KR20200116065A - 항암활성을 갖는 신규한 화합물 및 이의 제조방법 - Google Patents

항암활성을 갖는 신규한 화합물 및 이의 제조방법 Download PDF

Info

Publication number
KR20200116065A
KR20200116065A KR1020200038419A KR20200038419A KR20200116065A KR 20200116065 A KR20200116065 A KR 20200116065A KR 1020200038419 A KR1020200038419 A KR 1020200038419A KR 20200038419 A KR20200038419 A KR 20200038419A KR 20200116065 A KR20200116065 A KR 20200116065A
Authority
KR
South Korea
Prior art keywords
indol
methyl
methylphenylsulfonamido
propanamide
phenyl
Prior art date
Application number
KR1020200038419A
Other languages
English (en)
Other versions
KR102520437B1 (ko
Inventor
김성훈
김대규
이경
김민경
Original Assignee
재단법인 의약바이오컨버젼스연구단
동국대학교 산학협력단
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 재단법인 의약바이오컨버젼스연구단, 동국대학교 산학협력단 filed Critical 재단법인 의약바이오컨버젼스연구단
Publication of KR20200116065A publication Critical patent/KR20200116065A/ko
Application granted granted Critical
Publication of KR102520437B1 publication Critical patent/KR102520437B1/ko

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404—Indoles, e.g. pindolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4168—1,3-Diazoles having a nitrogen attached in position 2, e.g. clonidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D261/14—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/01—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having one nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/40—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Emergency Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

본 발명은 항암활성을 갖는 신규한 화합물 및 이의 제조방법에 관한 것으로, 보다 상세하게는 AIMP2-DX2의 발현을 억제하여 우수한 항암활성을 나타내는 신규한 화합물 및 이의 제조방법에 관한 것이다.
본 발명에 따른 상기 화학식 1로 표시되는 화합물은 AIMP2-DX2의 발현을 저해하는 효과가 매우 우수하여, AIMP2-DX2에 의해 유발되는 다양한 질환들, 특히 암 치료제 개발에 매우 유용하게 활용될 수 있다.

Description

항암활성을 갖는 신규한 화합물 및 이의 제조방법{Novel compound with anti-cancer activity, and method for preparing the same}
본 발명은 항암활성을 갖는 신규한 화합물 및 이의 제조방법에 관한 것으로, 보다 상세하게는 AIMP2-DX2의 발현을 억제하여 우수한 항암활성을 나타내는 신규한 화합물 및 이의 제조방법에 관한 것이다.
AIMP2(aminoacyl-tRNA synthetase complex-interacting multifunctional protein 2)는 아미노아실-tRNA 합성효소(aminoacyl-tRNA synthetase, ARS) 복합체의 형성에 관련된 단백질 중의 하나이다. AIMP2는 단백질 합성에서의 본원적인 기능 외에도, 신규한 암 억제자(tumor suppressor)로서 Smad2/3와의 직접적인 상호작용을 통하여 TGF-β의 신호전달을 강화시키는 기능이 있음이 알려져 있다.
본 발명자에 의한 대한민국 등록특허 제10-0762995호에 공지된 바와 같이, 폐암, 간암, 피부암, 유방암, 신장암, 골육종 등 다양한 암 세포주 및 조직에서는 AIMP2의 엑손(exon)2가 결손된 형태의 변이체인 AIMP2-DX2가 과발현되는 것이 관찰되었다. 한편, 정상 세포를 형질전환하여 AIMP2-DX2를 과발현되도록 하면, 야생형(WT) AIMP2의 수준이 크게 감소하며, AIMP2가 핵으로 이동하는 것을 막는 등 AIMP2의 활성이 억제되며, c-myc의 발현은 증가하고, 세포 성장은 촉진되는 등 TGF-β 신호의 기능 이상을 초래하는 것으로 나타났다. 이는 AIMP2-DX2와 암 발생과 진행 사이에 밀접한 관련성이 있음을 보여주는 것이다.
또한 본 발명자의 다른 대한민국 등록특허 제10-1067816호에서는 AIMP2가 TRAF2와의 상호작용을 통하여 TNF-α의 세포사멸 활성(apoptotic activity)을 매개하며, 이 활성은 AIMP2-DX2에 의해 조절된다는 것을 처음으로 공개하였다. 아울러 AIMP2-DX2는 염증 마커인 COX-2의 발현에도 영향을 미친다는 점을 규명하여, AIMP2-DX2의 활성을 억제함으로써 염증성 질환의 치료 효과를 낼 수 있음을 제시하였다.
이와 같이 AIMP2-DX2 단백질이 다양한 질환의 유발과 진행에 연관되어 있음이 밝혀짐에 따라 AIMP2-DX2가 신약 개발의 새로운 표적 물질로 대두되고 있다.
이에, 본 발명자들은 다양한 질환과 밀접하게 관련이 되어 있는 AIMP2-DX2의 발현을 저해할 수 있는 신규한 화합물을 개발하고자 예의 연구를 거듭한 결과, 본 명세서에서 화학식 1로 표시되는 화합물이 AIMP2-DX2의 발현을 억제하여 우수한 항암활성을 나타냄을 발견하고 본 발명을 완성하게 되었다.
따라서, 본 발명의 목적은 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 제공하는 것이다:
[화학식 1]
Figure pat00001
상기 화학식 1에서,
R1은 수소; 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸; C1~C5의 카복시메틸; C7~C10의 히드록시페닐알킬; 치환 또는 비치환의 C3~C8의 사이클로알킬; 치환 또는 비치환의 C1~C5의 아미노알킬;
Figure pat00002
;
Figure pat00003
;
Figure pat00004
;
Figure pat00005
;
Figure pat00006
;
Figure pat00007
;
Figure pat00008
;
Figure pat00009
;
Figure pat00010
;
Figure pat00011
;
Figure pat00012
;
Figure pat00013
;
Figure pat00014
;
Figure pat00015
;
Figure pat00016
;
Figure pat00017
;
Figure pat00018
;
Figure pat00019
;
Figure pat00020
;
Figure pat00021
;
Figure pat00022
;
Figure pat00023
;
Figure pat00024
;
Figure pat00025
;
Figure pat00026
또는
Figure pat00027
이고,
R2는 수소; C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐; 나프탈렌설포닐; 벤질설포닐; C1~C5의 직선형 또는 분지형 알킬 및 C1~C5의 직선형 또는 분지형 알킬아민기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤조일; 티오펜설포닐;
Figure pat00028
;
Figure pat00029
;
Figure pat00030
; C1~C5의 알킬옥시카보닐; 또는 페닐아미노카보닐이고,
R3은
Figure pat00031
;
Figure pat00032
;
Figure pat00033
;
Figure pat00034
;
Figure pat00035
;
Figure pat00036
;
Figure pat00037
;
Figure pat00038
;
Figure pat00039
;
Figure pat00040
;
Figure pat00041
;
Figure pat00042
;
Figure pat00043
;
Figure pat00044
;
Figure pat00045
;
Figure pat00046
;
Figure pat00047
;
Figure pat00048
;
Figure pat00049
;
Figure pat00050
;
Figure pat00051
;
Figure pat00052
;
Figure pat00053
;
Figure pat00054
;
Figure pat00055
;
Figure pat00056
;
Figure pat00057
;
Figure pat00058
;
Figure pat00059
;
Figure pat00060
;
Figure pat00061
;
Figure pat00062
;
Figure pat00063
;
Figure pat00064
;
Figure pat00065
;
Figure pat00066
;
Figure pat00067
;
Figure pat00068
;
Figure pat00069
;
Figure pat00070
Figure pat00071
;
Figure pat00072
;
Figure pat00073
;
Figure pat00074
;
Figure pat00075
;
Figure pat00076
;
Figure pat00077
;
Figure pat00078
;
Figure pat00079
;
Figure pat00080
;
Figure pat00081
,
Figure pat00082
;
Figure pat00083
;
Figure pat00084
;
Figure pat00085
;
Figure pat00086
;
Figure pat00087
;
Figure pat00088
;
Figure pat00089
;
Figure pat00090
;
Figure pat00091
;
Figure pat00092
;
Figure pat00093
;
Figure pat00094
;
Figure pat00095
;
Figure pat00096
;
Figure pat00097
;
Figure pat00098
;
Figure pat00099
;
Figure pat00100
;
Figure pat00101
;
Figure pat00102
;
Figure pat00103
;
Figure pat00104
;
Figure pat00105
;
Figure pat00106
;
Figure pat00107
;
Figure pat00108
;
Figure pat00109
;
Figure pat00110
;
Figure pat00111
;
Figure pat00112
;
Figure pat00113
;
Figure pat00114
;
Figure pat00115
또는
Figure pat00116
이다.
본 발명의 다른 목적은 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 암 예방 또는 치료용 약학적 조성물을 제공하는 것이다.
상기한 본 발명의 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 제공한다:
[화학식 1]
Figure pat00117
상기 화학식 1에서,
R1은 수소; 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸; C1~C5의 카복시메틸; C7~C10의 히드록시페닐알킬; 치환 또는 비치환의 C3~C8의 사이클로알킬; 치환 또는 비치환의 C1~C5의 아미노알킬;
Figure pat00118
;
Figure pat00119
;
Figure pat00120
;
Figure pat00121
;
Figure pat00122
;
Figure pat00123
;
Figure pat00124
;
Figure pat00125
;
Figure pat00126
;
Figure pat00127
;
Figure pat00128
;
Figure pat00129
;
Figure pat00130
;
Figure pat00131
;
Figure pat00132
;
Figure pat00133
;
Figure pat00134
;
Figure pat00135
;
Figure pat00136
;
Figure pat00137
;
Figure pat00138
;
Figure pat00139
;
Figure pat00140
;
Figure pat00141
;
Figure pat00142
또는
Figure pat00143
이고,
R2는 수소; C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐; 나프탈렌설포닐; 벤질설포닐; C1~C5의 직선형 또는 분지형 알킬 및 C1~C5의 직선형 또는 분지형 알킬아민기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤조일; 티오펜설포닐;
Figure pat00144
;
Figure pat00145
;
Figure pat00146
; C1~C5의 알킬옥시카보닐; 또는 페닐아미노카보닐이고,
R3은
Figure pat00147
;
Figure pat00148
;
Figure pat00149
;
Figure pat00150
;
Figure pat00151
;
Figure pat00152
;
Figure pat00153
;
Figure pat00154
;
Figure pat00155
;
Figure pat00156
;
Figure pat00157
;
Figure pat00158
;
Figure pat00159
;
Figure pat00160
;
Figure pat00161
;
Figure pat00162
;
Figure pat00163
;
Figure pat00164
;
Figure pat00165
;
Figure pat00166
;
Figure pat00167
;
Figure pat00168
;
Figure pat00169
;
Figure pat00170
;
Figure pat00171
;
Figure pat00172
;
Figure pat00173
;
Figure pat00174
;
Figure pat00175
;
Figure pat00176
;
Figure pat00177
;
Figure pat00178
;
Figure pat00179
;
Figure pat00180
;
Figure pat00181
;
Figure pat00182
;
Figure pat00183
;
Figure pat00184
;
Figure pat00185
;
Figure pat00186
Figure pat00187
;
Figure pat00188
;
Figure pat00189
;
Figure pat00190
;
Figure pat00191
;
Figure pat00192
;
Figure pat00193
;
Figure pat00194
;
Figure pat00195
;
Figure pat00196
;
Figure pat00197
,
Figure pat00198
;
Figure pat00199
;
Figure pat00200
;
Figure pat00201
;
Figure pat00202
;
Figure pat00203
;
Figure pat00204
;
Figure pat00205
;
Figure pat00206
;
Figure pat00207
;
Figure pat00208
;
Figure pat00209
;
Figure pat00210
;
Figure pat00211
;
Figure pat00212
;
Figure pat00213
;
Figure pat00214
;
Figure pat00215
;
Figure pat00216
;
Figure pat00217
;
Figure pat00218
;
Figure pat00219
;
Figure pat00220
;
Figure pat00221
;
Figure pat00222
;
Figure pat00223
;
Figure pat00224
;
Figure pat00225
;
Figure pat00226
;
Figure pat00227
;
Figure pat00228
;
Figure pat00229
;
Figure pat00230
;
Figure pat00231
또는
Figure pat00232
이다.
본 발명의 다른 목적을 달성하기 위하여 본 발명은 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 약학적 조성물을 제공한다.
이하, 본 발명을 상세히 설명한다.
본 발명은 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염을 제공한다:
[화학식 1]
Figure pat00233
상기 화학식 1에서,
R1은 수소; 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸; C1~C5의 카복시메틸; C7~C10의 히드록시페닐알킬; 치환 또는 비치환의 C3~C8의 사이클로알킬; 치환 또는 비치환의 C1~C5의 아미노알킬;
Figure pat00234
;
Figure pat00235
;
Figure pat00236
;
Figure pat00237
;
Figure pat00238
;
Figure pat00239
;
Figure pat00240
;
Figure pat00241
;
Figure pat00242
;
Figure pat00243
;
Figure pat00244
;
Figure pat00245
;
Figure pat00246
;
Figure pat00247
;
Figure pat00248
;
Figure pat00249
;
Figure pat00250
;
Figure pat00251
;
Figure pat00252
;
Figure pat00253
;
Figure pat00254
;
Figure pat00255
;
Figure pat00256
;
Figure pat00257
;
Figure pat00258
또는
Figure pat00259
이고,
R2는 수소; C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐; 나프탈렌설포닐; 벤질설포닐; C1~C5의 직선형 또는 분지형 알킬 및 C1~C5의 직선형 또는 분지형 알킬아민기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤조일; 티오펜설포닐;
Figure pat00260
;
Figure pat00261
;
Figure pat00262
; C1~C5의 알킬옥시카보닐; 또는 페닐아미노카보닐이고,
R3은
Figure pat00263
;
Figure pat00264
;
Figure pat00265
;
Figure pat00266
;
Figure pat00267
;
Figure pat00268
;
Figure pat00269
;
Figure pat00270
;
Figure pat00271
;
Figure pat00272
;
Figure pat00273
;
Figure pat00274
;
Figure pat00275
;
Figure pat00276
;
Figure pat00277
;
Figure pat00278
;
Figure pat00279
;
Figure pat00280
;
Figure pat00281
;
Figure pat00282
;
Figure pat00283
;
Figure pat00284
;
Figure pat00285
;
Figure pat00286
;
Figure pat00287
;
Figure pat00288
;
Figure pat00289
;
Figure pat00290
;
Figure pat00291
;
Figure pat00292
;
Figure pat00293
;
Figure pat00294
;
Figure pat00295
;
Figure pat00296
;
Figure pat00297
;
Figure pat00298
;
Figure pat00299
;
Figure pat00300
;
Figure pat00301
;
Figure pat00302
Figure pat00303
;
Figure pat00304
;
Figure pat00305
;
Figure pat00306
;
Figure pat00307
;
Figure pat00308
;
Figure pat00309
;
Figure pat00310
;
Figure pat00311
;
Figure pat00312
;
Figure pat00313
,
Figure pat00314
;
Figure pat00315
;
Figure pat00316
;
Figure pat00317
;
Figure pat00318
;
Figure pat00319
;
Figure pat00320
;
Figure pat00321
;
Figure pat00322
;
Figure pat00323
;
Figure pat00324
;
Figure pat00325
;
Figure pat00326
;
Figure pat00327
;
Figure pat00328
;
Figure pat00329
;
Figure pat00330
;
Figure pat00331
;
Figure pat00332
;
Figure pat00333
;
Figure pat00334
;
Figure pat00335
;
Figure pat00336
;
Figure pat00337
;
Figure pat00338
;
Figure pat00339
;
Figure pat00340
;
Figure pat00341
;
Figure pat00342
;
Figure pat00343
;
Figure pat00344
;
Figure pat00345
;
Figure pat00346
;
Figure pat00347
또는
Figure pat00348
이다.
본 발명에서 상기 "알킬"은 쇄 내에 1개 내지 5개의 탄소 원자를 포함하는, 직선형 또는 분지형일 수 있는 지방족 탄화수소 그룹을 의미한다. 바람직한 알킬 그룹은 상기 쇄 내에 1개 내지 3개의 탄소 원자를 포함한다. 보다 바람직한 알킬 그룹은 상기 쇄 내에 약 1개, 2개 또는 3개의 탄소 원자를 포함한다. 분지형은 하나 이상의 저급 알킬 그룹, 예를 들면, 메틸, 에틸 또는 프로필이 선형 알킬 쇄에 부착되어 있는 것을 의미한다. "저급알킬"은 직선형 또는 분지형일 수 있는 쇄 내에 1개 내지 5개의 탄소 원자를 갖는 그룹을 의미한다. "알킬"은 치환되지 않을 수 있거나 또는, 동일하거나 또는 상이할 수 있는 하나 이상의 치환체에 의해 임의로 치환될 수 있다.
본 발명에서 상기 "할로" 또는 "할로겐"은 불소 원자, 염소 원자, 브롬 원자 또는 요오드 원자를 의미한다.
본 발명에 개시된 기들이 "치환"이라고 표현될 때, 이 기들은 임의의 적당한 치환기 또는 치환기들로 치환될 수 있는 것이다. 치환기의 예시적인 예로서는 본 발명에에 개시된 예시적인 화합물과 구체예에서 살펴볼 수 있는 것들, 그리고 할로겐(클로로, 요도, 브로모 또는 플루오로 기), 알킬, 하이드록실, 알콕시, 알콕시알킬, 아미노, 알킬아미노, 카복시, 니트로, 아노, 티올, 티오에테르, 이민, 이미드, 아미딘, 구아니딘, 에나민, 아미노카보닐, 아실아미노, 포스포네이토, 포스핀, 티오카보닐, 설포닐, 설폰, 설폰아미드, 케톤, 알데히드, 에스테르, 우레아, 우레탄, 옥심, 하이드록실 아민, 알콕시아민, 아랄콕시아민, N-옥시드, 히드라진, 히드라지드, 히드라존, 아지드, 이소시아네이트, 이소티오시아네이트, 시아네이트, 티오시아네이트 등을 들 수 있다.
본 발명에서 상기 "알킬"은 쇄 내에 1개 내지 5개의 탄소 원자를 포함하는, 직선형 또는 분지형일 수 있는 지방족 탄화수소 그룹을 의미한다. 바람직한 알킬 그룹은 상기 쇄 내에 1개 내지 3개의 탄소 원자를 포함한다. 보다 바람직한 알킬 그룹은 상기 쇄 내에 약 1개, 2개 또는 3개의 탄소 원자를 포함한다. 분지형은 하나 이상의 저급 알킬 그룹, 예를 들면, 메틸, 에틸 또는 프로필이 선형 알킬 쇄에 부착되어 있는 것을 의미한다. "저급알킬"은 직선형 또는 분지형일 수 있는 쇄 내에 1개 내지 5개의 탄소 원자를 갖는 그룹을 의미한다. "알킬"은 치환되지 않을 수 있거나 또는, 동일하거나 또는 상이할 수 있는 하나 이상의 치환체에 의해 임의로 치환될 수 있다.
본 발명에서 상기 "할로" 또는 "할로겐"은 불소 원자, 염소 원자, 브롬 원자 또는 요오드 원자를 의미한다.
본 발명에 개시된 기들이 “치환”이라고 표현될 때, 이 기들은 임의의 적당한 치환기 또는 치환기들로 치환될 수 있는 것이다. 치환기의 예시적인 예로서는 본 발명에에 개시된 예시적인 화합물과 구체예에서 살펴볼 수 있는 것들, 그리고 할로겐(클로로, 요도, 브로모 또는 플루오로 기), 알킬, 하이드록실, 알콕시, 알콕시알킬, 아미노, 알킬아미노, 카복시, 니트로, 아노, 티올, 티오에테르, 이민, 이미드, 아미딘, 구아니딘, 에나민, 아미노카보닐, 아실아미노, 포스포네이토, 포스핀, 티오카보닐, 설포닐, 설폰, 설폰아미드, 케톤, 알데히드, 에스테르, 우레아, 우레탄, 옥심, 하이드록실 아민, 알콕시아민, 아랄콕시아민, N-옥시드, 히드라진, 히드라지드, 히드라존, 아지드, 이소시아네이트, 이소티오시아네이트, 시아네이트, 티오시아네이트 등을 들 수 있다.
본 발명의 일 양태에서, 상기 R1은 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; 또는 C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸이고,
상기 R2는 C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐이고,
상기 R3는
Figure pat00349
또는
Figure pat00350
일 수 있다.
바람직하게는, 상기 R1은 비치환된 C1~C5의 직선형 또는 분지형 알킬; 또는 비치환된 인돌일메틸이고,
상기 R2는 C1~C5의 직선형 또는 분지형 알킬로 치환되거나 비치환된 벤젠설포닐이고,
상기 R3는
Figure pat00351
또는
Figure pat00352
일 수 있다.
본 발명의 다른 일 양태에서, R1은 바람직하게는 수소, 사이클로헥산,
Figure pat00353
,
Figure pat00354
,
Figure pat00355
,
Figure pat00356
,
Figure pat00357
,
Figure pat00358
,
Figure pat00359
,
Figure pat00360
,
Figure pat00361
,
Figure pat00362
,
Figure pat00363
,
Figure pat00364
,
Figure pat00365
,
Figure pat00366
,
Figure pat00367
,
Figure pat00368
,
Figure pat00369
Figure pat00370
,
Figure pat00371
,
Figure pat00372
,
Figure pat00373
,
Figure pat00374
,
Figure pat00375
,
Figure pat00376
,
Figure pat00377
,
Figure pat00378
,
Figure pat00379
,
Figure pat00380
,
Figure pat00381
,
Figure pat00382
,
Figure pat00383
,
Figure pat00384
,
Figure pat00385
,
Figure pat00386
,
Figure pat00387
,
Figure pat00388
,
Figure pat00389
,
Figure pat00390
,
Figure pat00391
,
Figure pat00392
,
Figure pat00393
또는
Figure pat00394
일 수 있다.
본 발명의 다른 일 양태에서, 상기 R1은 가장 바람직하게는
Figure pat00395
,
Figure pat00396
,
Figure pat00397
,
Figure pat00398
,
Figure pat00399
,
Figure pat00400
,
Figure pat00401
,
Figure pat00402
,
Figure pat00403
,
Figure pat00404
,
Figure pat00405
,
Figure pat00406
,
Figure pat00407
,
Figure pat00408
,
Figure pat00409
,
Figure pat00410
,
Figure pat00411
,
Figure pat00412
,
Figure pat00413
,
Figure pat00414
,
Figure pat00415
,
Figure pat00416
,
Figure pat00417
,
Figure pat00418
,
Figure pat00419
,
Figure pat00420
또는
Figure pat00421
일 수 있다.
본 발명의 일 양태에서, 상기 R2는 바람직하게는 수소,
Figure pat00422
,
Figure pat00423
,
Figure pat00424
,
Figure pat00425
,
Figure pat00426
,
Figure pat00427
,
Figure pat00428
,
Figure pat00429
,
Figure pat00430
,
Figure pat00431
,
Figure pat00432
,
Figure pat00433
,
Figure pat00434
,
Figure pat00435
,
Figure pat00436
,
Figure pat00437
,
Figure pat00438
,
Figure pat00439
,
Figure pat00440
,
Figure pat00441
,
Figure pat00442
,
Figure pat00443
,
Figure pat00444
,
Figure pat00445
,
Figure pat00446
,
Figure pat00447
,
Figure pat00448
,
Figure pat00449
,
Figure pat00450
,
Figure pat00451
,
Figure pat00452
,
Figure pat00453
,
Figure pat00454
,
Figure pat00455
,
Figure pat00456
,
Figure pat00457
,
Figure pat00458
,
Figure pat00459
,
Figure pat00460
또는
Figure pat00461
일 수 있다.
본 발명의 일 양태에서, 상기 R3은 바람직하게는
Figure pat00462
;
Figure pat00463
;
Figure pat00464
;
Figure pat00465
;
Figure pat00466
;
Figure pat00467
;
Figure pat00468
;
Figure pat00469
;
Figure pat00470
;
Figure pat00471
;
Figure pat00472
;
Figure pat00473
;
Figure pat00474
;
Figure pat00475
;
Figure pat00476
;
Figure pat00477
;
Figure pat00478
;
Figure pat00479
;
Figure pat00480
;
Figure pat00481
;
Figure pat00482
;
Figure pat00483
;
Figure pat00484
;
Figure pat00485
;
Figure pat00486
;
Figure pat00487
;
Figure pat00488
;
Figure pat00489
;
Figure pat00490
;
Figure pat00491
;
Figure pat00492
;
Figure pat00493
;
Figure pat00494
;
Figure pat00495
;
Figure pat00496
;
Figure pat00497
;
Figure pat00498
;
Figure pat00499
;
Figure pat00500
;
Figure pat00501
Figure pat00502
;
Figure pat00503
;
Figure pat00504
;
Figure pat00505
;
Figure pat00506
;
Figure pat00507
;
Figure pat00508
;
Figure pat00509
;
Figure pat00510
;
Figure pat00511
;
Figure pat00512
,
Figure pat00513
;
Figure pat00514
;
Figure pat00515
;
Figure pat00516
;
Figure pat00517
,
Figure pat00518
,
Figure pat00519
Figure pat00520
,
Figure pat00521
,
Figure pat00522
,
Figure pat00523
,
Figure pat00524
,
Figure pat00525
,
Figure pat00526
,
Figure pat00527
,
Figure pat00528
,
Figure pat00529
,
Figure pat00530
,
Figure pat00531
,
Figure pat00532
또는
Figure pat00533
일 수 있다.
또한, 본 발명에서 상기 화학식 1의 화합물은
(S)-4-메틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
(R)-4-메틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((R)-4-methyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
(S)-4-메틸-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
(R)-4-메틸-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)-펜탄-2-일)벤젠설폰아미드 ((R)-4-methyl-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)-Pentan-2-yl)benzenesulfonamide),
(S)-N-(1-(1,1-디옥시도티오모폴리노)-4-메틸-1-옥소펜탄-2-일)-4-메틸벤젠설폰아미드((S)-N-(1-(1,1-dioxidothiomorpholino)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide),
N-((S)-1-((R)-2-(히드록시메틸)피롤리딘-1-일)-4-메틸-1-옥소펜탄-2-일)-4-메틸벤젠설폰아미드 (N-((S)-1-((R)-2-(hydroxymethyl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(피페리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(piperidin-1-yl)phenyl)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-메틸피페리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-methylpiperidin-1-yl)phenyl) pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-(4-메틸피페리딘-1-일)피리딘-3-일)펜탄아미드 ((S)-4-Methyl-2-(4-methylphenylsulfonamido)-N-(6-(4-methylpiperidin-1-yl)pyridin-3-yl)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-(4-메틸피페리딘-1-일)피리미딘-4-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(6-(4-methylpiperidin-1-yl)pyrimidin-4-yl)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-모폴리노피리딘-3-일)펜탄아미드) ((S)-4-Methyl-2-(4-methylphenylsulfonamido)-N-(6-morpholinopyridin-3-yl)pentanamide),
(S)-N-(6-((2S, 6R)-2,6-디메틸모폴리노)피리딘-3-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-N-(3-플루오로-4-모폴리노페닐)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(3-fluoro-4-morpholinophenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-N-(4-(1,1-디옥시도티오모폴리노)페닐)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드((S)-N-(4-(1,1-dioxidothiomorpholino)phenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-tert-부틸 4-(5-(4-메틸-2-(4-메틸페닐설폰아미도)펜타노일)피리딘-2-일)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(5-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido) pyridin-2-yl)piperazine-1-carboxylate),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(피롤리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(pyrrolidin-1-yl)phenyl)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(2-모폴리노에틸)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(2-morpholinoethyl)pentanamide)
(S)-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-니트로벤젠설폰아미드 ((S)-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-nitrobenzenesulfonamide),
(S)-3-아미노-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((S)-3-amino-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
(S)-2-(4-플루오로페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-fluorophenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
(S)-2-(4-브로모페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-bromophenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(4-(트리플루오로메틸)페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfonamido) pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(3-니트로페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(3-nitrophenylsulfonamido) pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(나프탈렌-1-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(naphthalene-1-sulfonamido)pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(나프탈렌-2-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(naphthalene-2-sulfonamido)pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(phenylsulfonamido)pentanamide),
(S)-벤질 4-메틸-2-(3-(페닐설포닐)프로판아미도)펜타노에이트((S)-Benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate),
(S)-2-(4-메톡시페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-methoxyphenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(티오펜-2-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(thiophene-2-sulfonamido)pentanamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(4-니트로페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)pentanamide),
(S)-2-(4-이소프로필페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-isopropylphenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
(S)-2-(비페닐-4-일설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(biphenyl-4-ylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
(S)-4-(벤질옥시)-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-(benzyloxy)-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
(S)-4-히드록시-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-hydroxy-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
(S)-벤질 4-(N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)설파모일)벤조에이트 ((S)-benzyl 4-(N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoate),
(S)-tert-부틸 3-(4-메틸페닐설폰아미도)-4-모폴리노-4-옥소부타노에이트 ((S)-tert-butyl 3-(4-methylphenylsulfonamido)-4-morpholino-4-oxobutanoate),
(S)-4-메틸-N-(1-모폴리노-1-옥소-3-페닐프로판-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(1-morpholino-1-oxo-3-phenylpropan-2-yl)benzenesulfonamide),
(S)-N-(3-하이드록시-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-hydroxy-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
(S)-4-메틸-N-(3-메틸-1-모폴리노-1-옥소부탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(3-methyl-1-morpholino-1-oxobutan-2-yl)benzenesulfonamide),
(R)-N-(3-메르캅토-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((R)-N-(3-mercapto-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
(2S,3S)-3-하이드록시-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)부탄아미드 ((2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)butanamide),
(2S,3S)-3-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)펜탄아미드 ((2S,3S)-3-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)pentanamide),
(S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-2-(4-메틸페닐설폰아미도)-4-(메틸티오)-N-(4-모폴리노페닐)부탄아미드 ((S)-2-(4-methylphenylsulfonamido)-4-(methylthio)-N-(4-morpholinophenyl)butanamide),
(S)-3-(1H-인돌-2-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-2-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) propanamide),
(S)-3-(1-메틸-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1-methyl-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) propanamide),
(S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-페닐프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-phenylpropanamide),
(S)-벤질 4-메틸-2-(4-메틸페닐설폰아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate),
(S)-벤질 4-메틸-2-(4-메틸벤즈아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(4-methylbenzamido)pentanoate),
(S)-벤질 2-(4-tert-부틸벤즈아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(4-tert-butylbenzamido)-4-methylpentanoate),
(S)-벤질 2-(벤조[d][1,3]다이옥솔-5-카복스아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(benzo[d][1,3]dioxole-5-carboxamido)-4-methylpentanoate),
(S)-벤질 2-(4-(tert-부톡시카르보닐아미노)벤즈아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(4-(tert-butoxycarbonylamino)benzamido)-4-methylpentanoate),
(S)-벤질 4-메틸-2-(3-(페닐설포닐)프로판아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate),
(S)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드((S)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-1-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-페닐우레아 ((S)-1-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-phenylurea),
(S)-4-tert-부틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤즈아미드 ((S)-4-tert-butyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzamide),
(S)-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-(페닐설포닐)프로판아미드 ((S)-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-(phenylsulfonyl)propanamide),
(S)-4-tert-부틸-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤즈아미드 ((S)-4-tert-butyl-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide),
(S)-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤조[d][1,3]디옥솔-5-카복스아미드 ((S)-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzo[d][1,3]dioxole-5-carboxamide),
(S)-4-메틸-N-(4-모폴리노페닐)-2-(3-(페닐설포닐)프로판아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(3-(phenylsulfonyl)propanamido)pentanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
(S)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)티아졸-2-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-3-(1H-인돌-3-일)-2-(2-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(2-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(3-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(3-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-2-(3,5-디메틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(3,5-dimethylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4 morpholinophenyl)propanamide),
(S)-2-(4-플루오로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-Fluorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(4-(트리플루오로메틸)페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfon-amido)propanamide),
(S)-3-(5-히드록시-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(5-Hydroxy-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-N-(3-(1H-인돌-3-일)-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(5-모폴리노티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(5-morpholinothiazol-2-yl)propan amide),
(S)-2-(2,4-디메틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(2,4-dimethylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
3-(3-에톡시-2-(4-메틸페닐설폰아미도)-3-옥소프로필)-1H-인돌-5-카르복실산 (3-(3-ethoxy-2-(4-methylphenylsulfonamido)-3-oxopropyl)-1H-indole-5-carboxylic acid),
(S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-(1-토실-1H-이미다졸-4-일)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-(1-tosyl-1H-imidazol-4-yl)propanamide),
(S)-N-(6-((2S,6R)-2,6-디메틸모폴린)피리딘-3-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도) ((S)-N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
(R)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((R)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-N-(3-플루오로-4-모폴리노페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(3-fluoro-4-morpholinophenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(4-니트로페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메톡시페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methoxyphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-이소프로필페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-isopropylphenylsulfonamido)-N-(4 morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-이소프로필페닐설폰아미도)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드((S)-3-(1H-indol-3-yl)-2-(4-isopropylphenylsulfonamido)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propenamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-methylthiazol-2-yl)propanamide),
(S)-N-(벤조[d]티아졸-2-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(benzo[d]thiazol-2-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판산 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanoic acid),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(5-모폴리노티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(5-morpholinothiazol-2-yl)pentanamide),
(S)-N-(5-(4-메톡시페닐)-1,3,4-티아디아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-N-(5-(4-메톡시페닐)이속사졸-3-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(5-(4-methoxyphenyl)isoxazol-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-N-(3-(4-메톡시페닐)이속사졸-5-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(3-(4-methoxyphenyl)isoxazol-5-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메틸)페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)pentanamide),
(S)-N-(4-(3,4-디메톡시페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(3,4-dimethoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-N-(4-(2-브로모-4-플루오로페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(2-bromo-4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-4-(2-아미노티아졸-4-일)페닐 4-메틸-2-(4-메틸페닐설폰아미도)펜타노에이트 ((S)-4-(2-aminothiazol-4-yl)phenyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate),
(S)-N-(4-(4-플루오로페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메톡시)페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethoxy)phenyl)thiazol-2-yl)pentanamide),
(S)-N-(4-(4-히드록시페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-hydroxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide)
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-p-톨릴티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-p-tolylthiazol-2-yl)pentanamide),
(S)-N-(4-(4-((S)-1-메톡시프로판-2-일옥시)페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-((S)-1-methoxypropan-2-yloxy)phenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-모폴리노페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-morpholinophenyl)thiazol-2-yl)pentanamide),
(S)-메틸 4-(2-(4-메틸-2-(4-메틸페닐설폰아미도)펜타노일)티아졸-4-일)벤조에이트 ((S)-methyl 4-(2-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido)thiazol-4-yl)benzoate),
(S)-4-(2-(4-메틸페닐설폰아미도)-3-(4-모폴리노페닐아미노)-3-옥소프로필)페닐 4-메틸벤젠설포네이트 ((S)-4-(2-(4-methylphenylsulfonamido)-3-(4-morpholinophenylamino)-3-oxopropyl)phenyl 4-methylbenzenesulfonate),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-이미다졸-4-일)-N-(4-(4-메톡시페닐)티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-imidazol-4-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
(S)-N-메톡시-N, 4-디메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-methoxy-N,4-dimethyl-2-(4-methylphenylsulfonamido)pentanamide),
(S)-3-(1H-인돌-3-일)-N-메톡시-N-메틸-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-methoxy-N-methyl-2-(4-methylphenylsulfonamido)propanamide),
(S)-N-(3-(1H-인돌-3-일)-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)propan-2-yl)-4-methylbenzenesulfonamide),
(S)-2-(4-tert-부틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-tert-butylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propan amide),
(S)-2-(4-브로모페닐설폰아미도)-N-(4-(2-클로로페닐)티아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-N-(4-(2-chlorophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-N-(4-(2,4-디메톡시페닐)티아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-N-(4-(2,4-dimethoxyphenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(thiazol-2-yl)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(5-메틸티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(5-methylthiazol-2-yl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-methylthiazol-2-yl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(5-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(5-methylthiazol-2-yl)propanamide),
(S)-메틸 4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조에이트 ((S)-methyl 4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate),
(S)-에틸 4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조에이트 ((S)-ethyl 4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate),
(S)-3-(4-벤조일페닐)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(4-benzoylphenyl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)-N-메틸벤즈아미드 ((S)-4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)-N-methylbenzamide),
(S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-(나프탈렌-2-일)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-(naphthalen-2-yl)propanamide),
(S)-tert-부틸 3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일카르바메이트 ((S)-tert-butyl 3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-ylcarbamate),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판산 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoic acid),
(S)-tert-부틸 4-(4-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-메톡시페닐)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(4-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-methoxyphenyl)piperazine-1-carboxylate),
(S)-3-(1H-인돌-3-일)-N-(2-메톡시-4-(피페라진-1-일)페닐)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(2-methoxy-4-(piperazin-1-yl)phenyl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-tert-부틸 4-(4-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)페닐)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(4-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)phenyl)piperazine-1-carboxylate),
(S)-3-(1H-인돌-3-일)-N-(2-메톡시-4-모폴리노페닐)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(2-methoxy-4-morpholinophenyl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(피페라진-1-일)페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(piperazin-1-yl)phenyl)propanamide),
(S)-3-(1-포밀-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1-formyl-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-N-(3-(4-메톡시페닐)이속사졸-5-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(3-(4-methoxyphenyl)isoxazol-5-yl)-2-(4-methylphenylsulfonamido)propanamide),
(S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로파노에이트 ((S)-benzyl 3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoate),
(S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸벤즈아미도)프로파노에이트 ((S)-benzyl 3-(1H-indol-3-yl)-2-(4-methylbenzamido)propanoate),
(S)-N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)-4-메틸벤즈아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)-4-methylbenzamide),
(S)-3-하이드록시-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-hydroxy-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-3-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)부탄아미드 ((S)-3-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)butanamide),
(S)-1-(3-(1H-인돌-3-일)-1-모폴리노-1-옥소프로판-2-일)-3-페닐우레아 ((S)-1-(3-(1H-indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-3-phenylurea),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(6-모폴리노피리딘-3-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(6-morpholinopyridin-3-yl)propanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(2-모폴리노피리미딘-5-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(2-morpholinopyrimidin-5-yl)propanamide),
(S)-2-(4-시아노페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-cyanophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
(S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(6-(트리플루오로메틸)피리딘-3-설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanamide),
(S)-메틸 4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노에이트 ((S)-methyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate),
(S)-3-(1H-벤조[d]이미다졸-1-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-benzo[d]imidazol-1-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(R)-3-(2,3-디옥소-3,4-디히드로퀴녹살린-1(2H)-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((R)-3-(2,3-dioxo-3,4-dihydroquinoxalin-1(2H)-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
(S)-N-(5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실)-5-(트리플루오로메틸)피콜린아미드 ((S)-N-(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)-5-(trifluoromethyl)picolinamide),
(S)-벤질 4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노에이트 ((S)-benzyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate),
(S)-벤질 3-(4-메틸페닐설폰아미도)-4-(4-모폴리노페닐아미노)-4-옥소부타노에이트 ((S)-benzyl 3-(4-methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoate),
(S)-4-메틸-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤즈아미드
((S)-4-methyl-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide),
2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)아세트아미드
(2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)acetamide),
(S)-3-(4-메틸페닐설폰아미도)-4-(4-모폴리노페닐아미노)-4-옥소부타노익산
((S)-3-(4-methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoic acid),
(S)-4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노익산
((S)-4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoic acid),
(S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-페닐프로판아미드
((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-phenylpropanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-페닐프로판아미드
((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-phenylpropanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-페닐프로판아미드
((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-phenylpropanamide),
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(티오펜-2-일)메틸)프로판아미드
((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(thiophen-2-ylmethyl)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(티오펜-2-일yl)메틸)프로판아미드
((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(thiophen-2-ylmethyl)propanamide),
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(2-메톡시페닐)사이아졸-2-일)프로판아미드
((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(2-methoxyphenyl)thiazol-2-yl)propanamide),
(S)-N-(3-(N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)설파모일)페닐)아세트아미드 ((S)-N-(3-(N-(4-methyl-1-morpholino-1-oxopentan-2-yl)sulfamoyl)phenyl)acetamide))
(S)-벤질 4-메틸-2-(3-페닐우레이도)펜타노에이트 ((S)-Benzyl 4-methyl-2-(3-phenylureido)pentanoate)
4-메틸-N-(2-모폴리노-2-옥소에틸)벤젠설폰아미드 (4-Methyl-N-(2-morpholino-2-oxoethyl)benzenesulfonamide)
4-메틸-N-(1-(모폴린-4-카보닐)사이클로헥실)벤젠설폰아미드 (4-Methyl-N-(1-(morpholine-4-carbonyl)cyclohexyl)benzenesulfonamide)
(S)-4-(N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자사이클로도데칸-10-일)펜탄-2-일)설파모일)벤조산 ((S)-4-(N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoic acid)
(S)-2-(4-히드록시페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-Hydroxyphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide)
(S)-4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조산 ((S)-4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoic acid)
(S)-2-아미노-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-Amino-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide)
(S)-N-(4-(4-아세틸피페라진-1-일)-2-메톡시페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-(4-Acetylpiperazin-1-yl)-2-methoxyphenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-N-(4-(4-아세틸피페라진-1-일)페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-(4-Acetylpiperazin-1-yl)phenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-N-(3-(1H-인돌-3-일)-1-(2-(4-모폴리노벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-morpholinobenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide)
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(4-모폴리노페닐)싸이아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(4-morpholinophenyl)thiazol-2-yl)propanamide)
(S)-메틸 4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조에이트 ((S)-Methyl 4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate)
(S)-벤질 3-(1H-인돌-3-일)-2-(6-(트리플루오로메틸)피리딘-3-설폰아미도)프로파노에이트 ((S)-Benzyl 3-(1H-indol-3-yl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanoate)
(S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-(4-니트로페닐)펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-(4-nitrophenyl)pentanediamide)
(S)-벤질 5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실카바메이트 ((S)-Benzyl 5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexylcarbamate)
(S)-6-아미노-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)헥산아미드 ((S)-6-Amino-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)hexanamide)
(S)-3,5-디메톡시-N-(5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실)벤즈아미드 ((S)-3,5-Dimethoxy-N-(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)benzamide)
(S)-N 5-(4-메톡시벤질)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-Methoxybenzyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide)
(S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-페닐펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-phenylpentanediamide)
(S)-2-(4-메틸페닐설폰아미도)-5-모폴리노-N-(4-모폴리노페닐)-5-옥소펜탄아미드 ((S)-2-(4-Methylphenylsulfonamido)-5-morpholino-N-(4-morpholinophenyl)-5-oxopentanamide)
(S)-N 5-(4-플루오로페닐)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-fluorophenyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide)
(S)-N 5-(4-tert-부틸페닐)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-tert-butylphenyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide)
(S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-(4-(트리플루오로메틸)페닐)펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-(4-(trifluoromethyl)phenyl)pentanediamide)
(S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 4-(4-니트로페닐)숙신아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 4-(4-nitrophenyl)succinamide)
(S)-N-(퓨란-2-일메틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(furan-2-ylmethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-N-(퓨란-2-일메틸)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(furan-2-ylmethyl)-3-(1H-indol-3-yl)propanamide)
(S)-3-(1H-인돌-3-일)-N-이소프로필-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-isopropyl-2-(4-methylphenylsulfonamido)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-이소프로필프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-isopropylpropanamide)
(S)-N-(3-(1H-인돌-3-일)-1-(2-(4-메톡시벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide)
(S)-2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로파노일)-N-(4-메톡시페닐)하이드라진카복사미드 ((S)-2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoyl)-N-(4-methoxyphenyl)hydrazinecarboxamide)
(S)-4-브로모-N-(1-(3,5-디메틸-1H-파이라졸-1-일)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide)
(S)-N-(3-(1H-인돌-3-일)-1-옥소-1-(3-페닐-1H-파이라졸-1-일)프로판-2-일)-4-브로모벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-oxo-1-(3-phenyl-1H-pyrazol-1-yl)propan-2-yl)-4-bromobenzenesulfonamide)
N-((S)-1-(2-((3S,5S,7S)-아다만탄-1-카보닐)하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 (N-((S)-1-(2-((3S,5S,7S)-adamantane-1-carbonyl)hydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(p-톨릴)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(p-tolyl)thiazol-2-yl)propanamide)
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-펜틸프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-phenethylpropanamide)
(S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-플루오로페닐)싸이아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-fluorophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-니트로페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-nitrophenyl)thiazol-2-yl)propanamide)
(S)-N-(3-(1H-인돌-3-일)-1-(2-(4-메톡시벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide)
(S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-시아노페닐)싸이아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-cyanophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-(트리플루오로메틸)페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide)
(S)-4-브로모-N-(1-(2-도데카노일하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(2-dodecanoylhydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide)
(S)-4-브로모-N-(1-(2-데카노일하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(2-decanoylhydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-펜틸프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-phenethylpropanamide)
N-((S)-1-(2-((3S,5S,7S)-아다만탄-1-카보닐)하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)-4-브로모벤젠설폰아미드 (N-((S)-1-(2-((3S,5S,7S)-adamantane-1-carbonyl)hydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide)
(S)-2-(4-브로모페닐설폰아미도)-N-(4-플루오로펜틸)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-fluorophenethyl)-3-(1H-indol-3-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-메톡시펜틸)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-methoxyphenethyl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(3-페닐프로필)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(3-phenylpropyl)propanamide)
(S)-N-((3R,5R,7R)-아다만탄-1-일)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판아미드 ((S)-N-((3R,5R,7R)-adamantan-1-yl)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanamide)
(S)-N-(3-(1H-인돌-3-일)-1-(4-(4-메톡시페닐)피페라진-1-일)-1-옥소프로판-2-일)-4-브로모벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide)
(S)-N-(3-(1H-인돌-3-일)-1-(4-(4-메톡시페닐)피페라진-1-일)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide)
(S)-N-((3R,5R,7R)-아다만탄-1-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-((3R,5R,7R)-adamantan-1-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-3-(1H-인돌-3-일)-N-(4-메톡시펜틸)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-methoxyphenethyl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(3-페닐프로필)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(3-phenylpropyl)propanamide)
(S)-N-(4-플루오로펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-fluorophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메틸)페닐)싸이아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide)
(S)-N-(2-(1H-인돌-3-일)에틸)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판아미드 ((S)-N-(2-(1H-indol-3-yl)ethyl)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanamide)
(S)-N-(3-(1H-인돌-3-일)-1-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-1-옥소프로판-2-일)-4-메틸벤즈아미드 ((S)-N-(3-(1H-indol-3-yl)-1-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-1-oxopropan-2-yl)-4-methylbenzamide)
(S)-2-(4-클로로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Chlorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide)
(S)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-2-(4-(트리플루오로메틸)페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-(trifluoromethyl)phenylsulfonamido)propanamide)
(S)-2-(4-플루오로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Fluorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-N-((1r,3R,5S,7S)-3,5-디메틸아다만탄-1-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-((1r,3R,5S,7S)-3,5-dimethyladamantan-1-yl)-3-(1H-indol-3-yl)propanamide)
(S)-2-(4-시아노페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Cyanophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide)
(S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸벤즈아미도)프로파노에이트 ((S)-Benzyl 3-(1H-indol-3-yl)-2-(4-methylbenzamido)propanoate)
(S)-2-(4-브로모페닐설폰아미도)-3-(5-히드록시-1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(5-hydroxy-1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-3-(5-메틸-1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-3-(5-methyl-1H-indol-3-yl)propanamide)
(S)-2-(4-브로모페닐설폰아미도)-3-(5-플루오로-1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(5-fluoro-1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide)
(S)-4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)에틸)벤조산 ((S)-4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)ethyl)benzoic acid)
(S)-N-(4-브로모펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-bromophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-N-(2-(1H-인돌-3-일)에틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(2-(1H-indol-3-yl)ethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-3-(1H-인돌-3-일)-N-(4-메틸펜틸)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-methylphenethyl)-2-(4-methylphenylsulfonamido)propanamide)
에틸 2-((S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-(1H-인돌-3-일)프로파노에이트 (Ethyl 2-((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1H-indol-3-yl)propanoate)
(S)-N-(4-클로로펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-chlorophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide)
2-((S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-(1H-인돌-3-일)프로판산 (2-((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1H-indol-3-yl)propanoic acid)
(S)-메틸 4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조에이트 ((S)-Methyl 4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate)
(S)-4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조산 ((S)-4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoic acid)
(S)-3-(벤조[d]옥사졸-2-일아미노)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(Benzo[d]oxazol-2-ylamino)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide)
(S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)벤즈아미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)benzamide)
(S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)니코틴아미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)nicotinamide) 또는
(S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)피리미딘-5-카복사미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)pyrimidine-5-carboxamide) 일 수 있다.
상기 나열한 화합물의 구조식, 이들 화합물의 AIMP2-DX2 발현 저해 효과 및 암 세포에 대한 세포독성을 하기 표 1에 나타내었다.
Figure pat00534
Figure pat00535
Figure pat00536
Figure pat00537
Figure pat00538
Figure pat00539
Figure pat00540
Figure pat00541
Figure pat00542
Figure pat00543
Figure pat00544
Figure pat00545
Figure pat00546
Figure pat00547
Figure pat00548
Figure pat00549
Figure pat00550
Figure pat00551
Figure pat00552
Figure pat00553
Figure pat00554
Figure pat00555
Figure pat00556
Figure pat00557
Figure pat00558
본 발명의 상기 화학식 1의 화합물은 약학적으로 허용가능한 염의 형태로 사용할 수 있다. 상기 염으로는 약학적으로나 생리학적으로 허용되는 다양한 유기산 또는 무기산에 의해 형성된 산 부가염이 유용하다. 적합한 유기산으로는, 예를 들면 카르복실산, 포스폰산, 술폰산, 아세트산, 프로피온산, 옥탄산, 데칸산, 글리콜산, 락트산, 푸마르산, 숙신산, 아디프산, 말산, 타르타르산, 시트르산, 글루탐산, 아스파르트산, 말레산, 벤조산, 살리실산, 프탈산, 페닐아세트산, 벤젠술폰산, 2-나프탈렌술폰산, 메틸황산, 에틸황산, 도데실황산 등을 사용할 수 있고, 적합한 무기산으로는, 예를 들면 염산, 황산 또는 인산 등을 사용할 수 있다.
본 발명의 화학식 1의 화합물은 약학적으로 허용가능한 염뿐만 아니라, 통상의 방법에 의해 제조될 수 있는 모든 염, 수화물 및 용매화물, 라세미체, 또는 입체 이성질체를 모두 포함할 수 있다.
본 발명의 일 실시예에 따르면, 상기 화합물들은 AIMP2-DX2의 발현을 저해하는 활성을 나타내는 것으로 확인이 되었다. 특히, 이와 같은 활성은 AIMP2-DX2 단백질의 안정화에 기여하는 HSP70과의 결합을 저해함으로써 발휘가 되는 것으로 확인이 되었다.
따라서, 본 발명이 제공하는 상기 화합물들은 AIMP2-DX2의 발현을 억제하는 활성을 나타내는 것을 특징으로 할 수 있다.
본 발명은 또한 하기 반응식에 의해 제조되는 제1항의 화합물 또는 이의 약학적으로 허용가능한 염의 제조방법을 제공한다:
[반응식 1]
Figure pat00559
상기 반응식 1에서,
R1, R2 및 R3는 제1항에서 정의한 바와 같다.
한편, 본 발명의 일실시예에 따르면, 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염은 AIMP2-DX2의 발현을 억제하여 암 세포에 대하여 우수한 세포독성을 나타내며, in vivo 종양모델에서도 종양의 성장을 억제하는 효과가 매우 우수한 것으로 확인이 되었다.
따라서, 본 발명은 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 암 예방 또는 치료용 약학적 조성물을 제공한다.
한편, 종래 보고된 바에 따르면, AIMP2-DX2의 발현을 저해하면 COX-2의 발현이 억제되어 염증 반응이 완화되는 것으로 확인이 된 바 있다(한국 등록특허 제1067816호). 따라서, AIMP2-DX2의 발현을 억제하는 본 발명의 화합물들은 염증성 질환에 대해서도 우수한 활성을 나타낼 수 있다.
이에, 본 발명은 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 약학적 조성물을 제공한다.
본 발명에서 상기 상기 염증성 질환은 염증성 피부질환, 크론씨 질환(Crohn's desease), 궤양성 대장염, 복막염, 골수염, 봉소염, 뇌막염, 뇌염, 췌장염, 외상 유발 쇼크, 기관지 천식, 알레르기성 비염, 낭포성 섬유증, 뇌졸중, 급성 기관지염, 만성 기관지염, 급성 세기관지염, 만성 세기관지염, 골관절염, 통풍, 척추관절병증, 강직성 척추염, 라이터 증후군, 건선성 관절병증, 장질환 척추염, 연소자성 관절병증, 연소자성 강직성 척추염, 반응성 관절병증, 감염성 관절염, 후-감염성 관절염, 임균성 관절염, 결핵성 관절염, 바이러스성 관절염, 진균성 관절염, 매독성 관절염, 라임 병, '혈관염 증후군'과 관련된 관절염, 결절성 다발동맥염, 과민성 혈관염, 루게닉 육아종증, 류마티스성 다발성근육통, 관절 세포 동맥염, 칼슘 결정 침착 관절병증, 가성 통풍, 비-관절 류마티즘, 점액낭염, 건초염, 상과염(테니스 엘보), 신경병증성 관절 질환(charco and joint), 출혈성 관절증(hemarthrosic), 헤노흐-쉔라인 자반병, 비후성 골관절병증, 다중심성 세망조직구종, 수르코일로시스(surcoilosis), 혈색소증, 겸상 적혈구증 및 기타 혈색소병증, 고지단백혈증, 저감마글로불린혈증, 가족성 지중해열, 베하트 병, 전신성 홍반성 루푸스, 재귀열, 건선, 다발성 경화증, 패혈증, 패혈성 쇼크, 다장기 기능장애 증후군, 급성 호흡곤란 증후군, 만성 폐쇄성 폐질환(chronic obstructive pulmonary disease), 류마치스성 관절염(rheumatoid arthritis), 급성 폐손상(acute lung injury) 및 기관지 폐 형성장애(broncho-pulmonary dysplasia)로 이루어진 군에서 선택될 수 있으나, 이에 제한되는 것은 아니다.
본 발명에 따른 약학적 조성물은 상기 화학식 1의 화합물 또는 이의 약학적으로 허용가능한 염을 단독으로 함유하거나 또는 하나 이상의 약학적으로 허용되는 담체, 부형제 또는 희석제를 추가로 함유할 수 있다.
약학적으로 허용되는 담체로는 예컨대, 경구 투여용 담체 또는 비경구 투여용 담체를 추가로 포함할 수 있다. 경구 투여용 담체는 락토스, 전분, 셀룰로스 유도체, 마그네슘 스테아레이트, 스테아르산 등을 포함할 수 있다. 또한, 비경구 투여용 담체는 물, 적합한 오일, 식염수, 수성 글루코스 및 글리콜 등을 포함할 수 있으며, 안정화제 및 보존제를 추가로 포함할 수 있다. 적합한 안정화제로는 아황산수소나트륨, 아황산나트륨 또는 아스코르브산과 같은 항산화제가 있다. 적합한 보존제로는 벤즈알코늄 클로라이드, 메틸- 또는 프로필-파라벤 및 클로로부탄올이 있다. 그 밖의 약학적으로 허용되는 담체로는 다음의 문헌에 기재되어 있는 것을 참고로 할 수 있다(Remington's Pharmaceutical Sciences, 19th ed., Mack Publishing Company, Easton, PA, 1995).
본 발명의 약학적 조성물은 인간을 비롯한 포유동물에 어떠한 방법으로도 투여할 수 있다. 예를 들면, 경구 또는 비경구적으로 투여할 수 있다. 비경구적인 투여방법으로는 이에 한정되지는 않으나, 정맥내, 근육내, 동맥내, 골수내, 경막내, 심장내, 경피, 피하, 복강내, 비강내, 장관, 국소, 설하 또는 직장내 투여일 수 있다. 예컨대, 본 발명의 약학적 조성물을 주사형 제형으로 제조하여 이를 30 게이지의 가는 주사 바늘로 피부를 가볍게 단자(prick)하는 방법, 또는 피부에 직접적으로 도포하는 방법으로 투여될 수 있다.
본 발명의 약학적 조성물은 상술한 바와 같은 투여 경로에 따라 경구 투여용 또는 비경구 투여용 제제로 제형화 할 수 있다.
경구 투여용 제제의 경우에 본 발명의 조성물은 분말, 과립, 정제, 환제, 당의정제, 캡슐제, 액제, 겔제, 시럽제, 슬러리제, 현탁액 등으로 당업계에 공지된 방법을 이용하여 제형화될 수 있다. 예를 들어, 경구용 제제는 활성성분을 고체 부형제와 배합한 다음 이를 분쇄하고 적합한 보조제를 첨가한 후 과립 혼합물로 가공함으로써 정제 또는 당의정제를 수득할 수 있다. 적합한 부형제의 예로는 락토즈, 덱스트로즈, 수크로즈, 솔비톨, 만니톨, 자일리톨, 에리스리톨 및 말티톨 등을 포함하는 당류와 옥수수 전분, 밀 전분, 쌀 전분 및 감자 전분 등을 포함하는 전분류, 셀룰로즈, 메틸 셀룰로즈, 나트륨 카르복시메틸셀룰로오즈 및 하이드록시프로필메틸-셀룰로즈 등을 포함하는 셀룰로즈류, 젤라틴, 폴리비닐피롤리돈 등과 같은 충전제가 포함될 수 있다. 또한, 경우에 따라 가교결합 폴리비닐피롤리돈, 한천, 알긴산 또는 나트륨 알기네이트 등을 붕해제로 첨가할 수 있다. 나아가, 본 발명의 약학적 조성물은 항응집제, 윤활제, 습윤제, 향료, 유화제 및 방부제 등을 추가로 포함할 수 있다.
비경구 투여용 제제의 경우에는 주사제, 크림제, 로션제, 외용연고제, 오일제, 보습제, 겔제, 에어로졸 및 비강 흡입제의 형태로 당업계에 공지된 방법으로 제형화할 수 있다. 이들 제형은 모든 제약 화학에 일반적으로 공지된 처방서인 문헌(Remington's Pharmaceutical Science, 15th Edition, 1975. Mack Publishing Company, Easton, Pennsylvania 18042, Chapter 87: Blaug, Seymour)에 기재되어 있다.
본 발명의 약학적 조성물의 총 유효량은 단일 투여량(single dose)으로 환자에게 투여될 수 있으며, 다중 투여량(multiple dose)으로 장기간 투여되는 분할 치료 방법(fractionated treatment protocol)에 의해 투여될 수 있다. 본 발명의 약학적 조성물은 질환의 정도에 따라 유효성분의 함량을 달리할 수 있다. 바람직하게는 본 발명의 약학적 조성물의 전체 용량은 1일당 환자 체중 1㎏ 당 약 0.01ug 내지 1,000mg, 가장 바람직하게는 0.1ug 내지 100mg일 수 있다. 그러나 상기 본 발명의 약학적 조성물의 투여 용량은 투여 경로 및 치료 횟수뿐만 아니라 환자의 연령, 체중, 건강 상태, 성별, 질환의 중증도, 식이 및 배설율 등 다양한 요인들을 고려하여 환자에 대한 유효 투여량이 결정되는 것이므로, 이러한 점을 고려할 때 당 분야의 통상적인 지식을 가진 자라면 상기 본 발명의 약학적 조성물을 퇴행성 신경질환 치료제로서의 특정한 용도에 따른 적절한 유효 투여량을 결정할 수 있을 것이다. 본 발명에 따른 약학적 조성물은 본 발명의 효과를 보이는 한 그 제형, 투여 경로 및 투여 방법에 특별히 제한되지 아니한다.
본 발명에서 상기 '치료'는 암 또는 염증성 질환의 증상을 개선시키는 것을 포괄적으로 지칭하고, 이는 바람직하게는 암 또는 염증성 질환을 치유하거나, 실질적으로 예방하거나, 또는 상태를 개선시키는 것을 포함할 수 있으며, 암 또는 염증성 질환으로부터 비롯된 한 가지 증상 또는 대부분의 증상을 완화시키거나, 치유하거나 예방하는 것을 포함하나, 이에 제한되는 것은 아니다.
본 발명에 따른 상기 화학식 1로 표시되는 화합물은 AIMP2-DX2의 발현을 저해하는 효과가 매우 우수하여, AIMP2-DX2에 의해 유발되는 다양한 질환들, 특히 암 치료제 개발에 매우 유용하게 활용될 수 있다.
도 1은 nanoruciferase-DX2 또는 -AIMP2를 발현하는 A549 세포에 본 발명의 63번 화합물을 농도별로 4시간 동안 처리한 후 형광을 측정하여 AIMP2-DX2 및 AIMP2에 대한 IC50 산출한 결과이다.
도 2는 본 발명의 63번 화합물이 AIMP2-DX2와 HPS70의 결합을 저해한다는 것을 in vitro pull-down assay를 통해 확인한 결과이다. 정제된 AIMP2-DX2-His6 및 HSP70 단백질을 혼합하고 63번 화합물을 농도별로 4시간 동안 처리한 후 AIMP2-DX2는 Ni-IDA 레진으로 침전시키고, AIMP2-DX2와 함께 침전된 HSP70을 SDS-PAGE 및 쿠마시 염색으로 시각화 한 것이다.
도 3은 H460 세포가 이식된 마우스에 63번 화합물 (50mg/kg)을 이틀마다 한 번씩 총 15일간 복강으로 투여하면서 종양의 성장을 관찰한 결과이다(A: 투여 종료 후 각 마우스 및 종양의 육안 관찰, B: 시간의 경과에 따른 종양의 성장 곡선, C: 투여 종료 시점에서 수득한 각 종양의 무게, D: 투여 기간 동안 동물의 체중변화).
도 4는 본 발명에 따른 상기 화학식 1의 화합물 중 55번 화합물 및 89번 화합물의 암 세포 성장 저해 효과 및 약물의 종양 분포도를 H460 xenograft 동물모델에서 실험한 결과이다. 양성대조군으로 Taxol을 이용하였다.
이하 본 발명을 상세히 설명한다.
단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명의 내용이 하기 실시예에 한정되는 것은 아니다.
실시예 1: 화합물의 제조
본 발명에서 상기 화학식 1의 화합물은 하기 반응식 1에 따라서 제조되었다:
[반응식 1]
Figure pat00560
상기 반응식에서, R1, R2 및 R3는 상기 정의한 바와 같다.
구체적으로, 출발물질인 산(1) (1.0 당량), 2M NaOH 용액 (1.0 당량)을 취하였다. 혼합물을 맑은 용액이 형성 될 때까지 0 ℃에서 수 분간 교반 하였다. 상기 용액에 설포닐 클로라이드 (1.05 당량), DIPEA (1.1 당량) 및 아세톤을 첨가 하였다. 혼합물을 0 ℃에서 10 분 동안 교반 한 후, 실온에서 12 시간 동안 교반 하였다. 반응 종료 후, 혼합물을 에테르로 세척하여 유기 불순물을 제거 하였다. 합쳐진 유기층을 2M NaOH로 다시 세척 하였다. 수성층에 2N HCl을 0 ℃에서 pH가 2가 될 때까지 첨가 하였다. 이후 전체 수성 혼합물을 에틸 아세테이트, 물 및 염수로 추출 하였다. 유기 용매를 MgSO4상에서 건조시키고 진공에서 증발 시켜서 화합물 (2)를 수득 하였다.
15 mL의 DMF 또는 DCM : THF = 1 : 1에 상기 화합물 (2) (2 당량), 아민 (1.1 당량), EDCl (1.1 당량) 및 HOBt (1.1 당량)를 첨가 하였다. 혼합물을 실온에서 밤새 교반하고, 이어서 에틸 아세테이트, 물 및 염수로 추출 하였다. 유기층을 MgSO4상에서 건조시키고 진공에서 증발시켜 화합물 (3)의 조생성물로서 수득하고,이를 컬럼 크로마토그래피로 정제하여 순수한 화합물 (3)을 수득 하였다.
상기 방법에 따라 제조된 상기 화학식 1 화합물의 구체적인 예시, 구조 및 NMR 분석결과를 이하 구체적으로 나타내었다.
( S )-4-Methyl- N -(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.70 (d, J = 8.40 Hz, 2H), 7.29 (d, J = 8.00 Hz, 2H), 5.74 (d, J = 9.60 Hz, 1H), 4.06 - 4.01 (m, 1H), 3.61 - 3.51 (m, 2H), 3.41 - 3.36 (m, 1H), 3.31 - 3.14 (m, 5H), 2.42 (s, 3H), 2.00 - 1.93 (m, 1H), 1.50 - 1.43 (m, 1H), 1.17 - 1.11 (m, 1H), 0.95 (d, J = 6.80 Hz, 3H), 0.92 (d, J = 6.80 Hz, 3H)
( R )-4-methyl- N -(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.70 (d, J = 8.80 Hz, 2H), 7.29 (d, J = 8.40 Hz, 2H), 5.78 (d, J = 9.60 Hz, 1H), 4.08 - 4.02 (m, 1H), 3.59 - 3.42 (m, 2H), 3.41 - 3.32 (m, 1H), 3.31 - 3.15 (m, 5H), 2.41 (s, 3H), 1.99 - 1.92 (m, 1H), 1.50 - 1.42 (m, 1H), 1.19 - 1.12 (m, 1H), 0.95 (d, J = 6.80 Hz, 3H), 0.92 (d, J = 6.80 Hz, 3H)
( S )-4-Methyl- N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.71 (d, J = 8.00 Hz, 2H), 7.27 (d, J = 8.00 Hz, 2H), 5.59 (d, J = 10.0 Hz, 1H), 4.25 - 4.19 (m, 1H), 3.78 - 3.71 (m, 2H), 3.69 - 3.37 (m, 11H), 3.22 - 3.12 (m, 3H), 2.40 (s, 3H), 1.98 - 1.91 (m, 1H), 1.49 - 1.33 (m, 2H), 0.91 (t, J = 6.00 Hz, 6H)
( R )-4-methyl- N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)-Pentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.71 (d, J = 8.00 Hz, 2H), 7.27 (d, J = 8.40 Hz, 2H), 5.66 (d, J = 9.60 Hz, 1H), 4.26 - 4.20 (m, 1H), 3.79 - 3.67 (m, 2H), 3.66 - 3.38 (m, 11H), 3.23 - 3.12 (m, 3H), 2.40 (s, 3H), 1.97 - 1.90 (m, 1H), 1.49 - 1.33 (m, 2H), 0.92 (d, J = 4.20 Hz, 3H), 0.89 (d, J = 5.60 Hz, 3H)
( S )- N -(1-(1,1-dioxidothiomorpholino)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.73 (d, J = 7.60 Hz, 2H), 7.34 (d, J = 7.60 Hz, 2H), 5.59 (d, J = 9.60 Hz, 1H), 4.40 (d, J = 14.0 Hz, 1H), 4.05 - 3.99 (m, 1H), 3.81 (d, J = 14.8 Hz, 1H), 3.66 (t, J = 12.6 Hz, 1H), 3.32 (t, J = 12.2 Hz, 1H), 2.88 (t, J = 11.2 Hz, 2H), 2.61 - 2.56 (m, 1H), 2.50 - 2.40 (m, 4H), 1.97 - 1.92 (m, 1H), 1.52 - 1.46 (m, 1H), 1.22 - 1.16 (m, 1H), 0.93 (d, J = 6.40 Hz, 3H), 0.85 (d, J = 6.40 Hz, 3H)
N -(( S )-1-(( R )-2-(hydroxymethyl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.70 (d, J = 8.20 Hz, 2H), 7.28 (d, J = 7.60 Hz, 2H), 5.60 (d, J = 9.60 Hz, 1H), 4.05 (dd, J = 3.00, 7.40 Hz, 1H), 3.97 - 3.91 (m, 1H), 4.06 - 4.03 (m, 1H), 3.97 - 3.91 (m, 1H), 3.63 - 3.61 (m, 1H), 3.52 - 3.49 (m, 1H), 3.29 - 3.25 (m, 2H), 2.42 (s, 3H), 1.94 - 1.85 (m, 2H), 1.77 - 1.68 (m, 2H), 1.56 - 1.47 (m, 2H), 1.25 - 1.19 (m, 1H), 0.94 (d, J = 3.20 Hz, 3H), 0.93 (d, J = 4.00 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(piperidin-1-yl)phenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.76 (d, J = 8.00 Hz, 2H), 7.22 - 7.12 (m, 4H), 6.82 - 6.78 (m, 2H), 5.48 (s, 1H), 3.84 - 3.82 (m, 1H), 3.07 (t, J = 5.60 Hz, 4H), 2.32 (s, 3H), 1.71 - 1.46 (m, 8H), 0.85 (d, J = 6.00 Hz, 3H), 0.72 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(4-methylpiperidin-1-yl)phenyl) pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.76 (d, J = 8.00 Hz, 2H), 7.21 - 7.12 (m, 4H), 6.81 - 6.77 (m, 2H), 5.66 (d, J = 7.60 Hz, 1H), 3.88 - 3.83 (m, 1H), 3.56 - 3.53 (m, 2H), 2.65 - 2.58 (m, 2H), 2.31 (s, 3H), 1.73 - 1.70 (m, 2H), 1.62 - 1.56 (m, 2H), 1.50 - 1.45 (m, 2H), 1.37 - 1.25 (m, 2H), 0.97 (d, J = 6.40 Hz, 3H), 0.84 (d, J = 6.00 Hz, 3H), 0.71 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(6-(4-methylpiperidin-1-yl)pyridin-3-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.98 (d, J = 2.80 Hz, 1H), 7.76 (d, J = 8.40 Hz, 2H), 7.48 (dd, J = 2.80, 8.80 Hz, 1H ), 7.22 (d, J = 8.00 Hz, 2H), 6.52 (d, J = 8.80 Hz, 1H), 5.85 (d, J = 8.00 Hz, 1H), 4.16 - 4.11 (m, 2H), 3.91 - 3.86 (m, 1H), 2.78 - 2.72 (m, 2H), 2.32 (s, 3H), 1.69 - 1.47 (m, 6H), 1.23 - 1.13 (m, 2H), 0.95 (d, J = 6.00 Hz, 3H), 0.83 (d, J = 6.40 Hz, 3H), 0.68 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(6-(4-methylpiperidin-1-yl)pyrimidin-4-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.76 (s, 1H), 8.31 (s, 1H), 7.75 (d, J = 8.40 Hz, 2H), 7.22 (d, J = 8.40 Hz, 3H), 6.21 (s, 2H), 4.37 (s, 2H), 3.85 (s, 1H), 2.90 - 2.84 (m, 2H), 2.31 (s, 3H), 1.80 - 1.60 (m, 4H), 1.53 - 1.1.47 (m, 2H), 1.19 - 1.09 (m, 2H), 0.97 (d, J = 6.80 Hz, 3H), 0.82 (d, J = 6.80 Hz, 3H), 0.70 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl) pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.95 (s, 1H), 7.76 (d, J = 8.00 Hz, 2H), 7.28 - 7.16 (m, 4H), 6.84 - 6.71 (m, 2H), 5.49 (d, J = 7.60 Hz, 1H), 3.84 (t, J = 4.80 Hz, 4H), 3.08 (t, J = 4.80 Hz, 4H), 2.33 (s, 3H), 1.60-1.58 (m, 2H), 1.50 - 1.46 (m, 1H), 0.84 (d, J = 6.00 Hz, 3H), 0.70 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(6-morpholinopyridin-3-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 8.04 (d, J = 2.40 Hz, 1H), 7.77 (d, J = 8.40 Hz, 2H), 7.59 (dd, J = 2.80, 9.20 Hz, 1H ), 7.23 (d, J = 8.40 Hz, 2H), 6.52 (d, J = 8.80 Hz, 1H), 5.90 (d, J = 8.00 Hz, 1H), 3.92 - 3.86 (m, 1H), 3.80 (t, J = 5.00 Hz, 4H), 3.42 (t, J = 4.60 Hz, 4H), 2.34 (s, 3H), 1.60 - 1.48 (m, 3H), 0.83 (d, J = 6.00 Hz, 3H), 0.67 (d, J = 6.00 Hz, 3H)
( S )- N -(6-((2 S ,6 R )-2,6-dimethylmorpholino)pyridin-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.03 (d, J = 2.40 Hz, 2H), 8.00 (s, 1H), 7.77 (d, J = 8.40 Hz, 2H), 7.61 (dd, J = 2.80, 9.20 Hz, 1H), 7.26 (d, J = 8.00 Hz, 2H), 6.53 (d, J = 9.20 Hz, 1H), 5.48 (d, J = 7.60 Hz, 1H), 4.13 (q, J = 7.20 Hz, 1H), 3.95 (dd, J = 2.00, 12.8 Hz, 2H), 3.87 - 3.82 (m, 1H), 3.72 - 3.68 (m, 2H), 2.49 - 2.44 (m, 2H), 2.35 (s, 3H), 1.63 - 1.58 (m, 2H), 1.52 - 1.47 (m, 1H), 1.25 (d, J = 8.00 Hz, 6H), 0.85 (d, J = 6.00 Hz, 3H), 0.69 (d, J = 6.40 Hz, 3H)
( S )- N -(3-fluoro-4-morpholinophenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.81 (s, 1H), 7.76 (d, J = 8.00 Hz, 2H), 7.29 (d, J = 8.00 Hz, 2H), 7.26 - 7.21 (m, 1H), 6.98 (d, J = 6.00 Hz, 1H), 6.85 (t, J = 9.00 Hz, 1H), 4.90 (d, J = 7.20 Hz, 1H), 3.86 (t, J = 4.60 Hz, 4H), 3.77 - 3.72 (m, 1H), 3.04 (t, J = 4.40 Hz, 4H), 2.38 (s, 3H), 1.67 - 1.43 (m, 3H), 0.86 (d, J = 6.40 Hz, 3H), 0.68 (d, J = 6.40 Hz, 3H)
( S )- N -(4-(1,1-dioxidothiomorpholino)phenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.78 (d, J = 8.40 Hz, 2H), 7.33 (d, J = 9.20 Hz, 2H), 7.28 (d, J = 8.40 Hz, 2H), 6.84 (d, J = 8.40 Hz, 2H), 5.31 (d, J = 7.20 Hz, 1H), 3.82 - 3.76 (m, 5H), 3.10 (t, J = 5.20 Hz, 4H), 2.37 (s, 3H), 1.67 - 1.45 (m, 3H), 0.84 (d, J = 6.40 Hz, 3H), 0.65 (d, J = 6.40 Hz, 3H)
( S )- tert -butyl 4-(5-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido) pyridin-2-yl)piperazine-1-carboxylate
1H-NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 8.02 (d, J = 2.80 Hz, 1H), 7.77 (d, J = 8.40 Hz, 2H), 7.6 (dd, J = 2.80, 9.20 Hz, 1H), 7.25 (d, J = 8.40 Hz, 2H), 6.55 (d, J = 9.20 Hz, 2H), 5.58 (d, J = 8.00 Hz, 1H), 3.89 - 3.84 (m, 1H), 3.53 - 3.43 (m, 8H), 2.33 (s, 3H), 1.62 - 1.59 (m, 2H), 1.52 - 1.48 (m, 10H), 0.85 (d, J = 5.60 Hz, 3H), 0.69 (d, J = 6.00 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(pyrrolidin-1-yl)phenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.76 (d, J = 8.00 Hz, 2H), 7.71 (s, 1H), 7.23 (d, J = 8.00 Hz, 2H), 7.08 - 7.04 (m, 2H), 6.43 - 6.39 (m, 2H), 5.47 (d, J = 7.60 Hz, 1H), 3.85 - 3.79 (m, 1H), 3.22 (t, J = 6.40 Hz, 4H), 2.43 (s, 3H), 2.03 - 1.96 (m, 4H), 1.64 - 1.47 (m, 3H), 0.86 (d, J = 6.40 Hz, 3H), 0.74 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(2-morpholinoethyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.76 - 7.73 (m, 2H), 7.29 (d, J = 8.00 Hz, 2H), 6.65 (t, J = 4.80 Hz, 1H), 5.50 (d, J = 7.20 Hz, 1H), 3.71 - 3.63 (m, 5H), 3.29 - 3.23 (m, 1H), 3.18 - 3.11 (m, 1H), 2.46 - 2.37 (m, 9H), 1.57 - 1.50 (m, 2H), 1.44 - 1.39 (m, 1H), 0.83 (d, J = 6.40 Hz, 3H), 0.67 (d, J = 6.00 Hz, 3H)
( S )- N -(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-nitrobenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 8.62 (t, J = 2.00 Hz, 1H), 8.43 - 8.40 (m, 1H), 8.17 - 8.14 (m, 1H), 7.73 (t, J = 8.00 Hz, 1H), 5.82 (d, J = 10.0 Hz, 1H), 4.28 - 4.22 (m, 1H), 3.66 - 3.58 (m, 1H), 3.57 - 3.51 (m, 2H), 3.39 - 3.21 (m, 5H), 1.97 - 1.90 (m, 1H), 1.53 - 1.45 (m, 1H), 1.25 - 1.18 (m, 1H), 0.98 (d, J = 6.80 Hz, 3H), 0.94 (d, J = 6.40 Hz, 3H)
( S )-3-Amino- N -(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.23 (t, J = 7.80 Hz, 1H), 7.14 - 7.09 (m, 2H), 6.80 (dd, J = 1.40, 7.80 Hz, 1H), 4.11 - 4.02 (m, 3H), 3.61 - 3.53 (m, 2H), 3.44 - 3.35 (m, 3H), 3.29 - 3.20 (m, 3H), 1.97 - 1.93 (m, 1H), 1.51 - 1.41 (m, 1H), 1.19 - 1.13 (m, 1H), 0.95 (d, J = 6.00 Hz, 3H), 0.91 (d, J = 6.80 Hz, 3H)
( S )-2-(4-Fluorophenylsulfonamido)-4-methyl- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.98 (s, 1H), 7.91 - 7.87 (m, 2H), 7.22 - 7.19 (m, 2H), 7.12 - 7.07 (m, 2H), 6.80 (dd, J = 2.20, 6.60 Hz, 2H), 5.74 (d, J = 7.60 Hz, 1H), 3.85 (t, J = 5.00 Hz, 4H), 3.09 (t, J = 4.80 Hz, 4H), 1.63 - 1.57 (m, 2H), 1.53 - 1.48 (m, 1H), 0.86 (d, J = 6.40 Hz, 3H), 0.73 (d, J = 6.00 Hz, 3H)
( S )-2-(4-Bromophenylsulfonamido)-4-methyl- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.72 (d, J = 8.40 Hz, 2H), 7.59 (d, J = 8.40 Hz, 2H), 7.45 (s, 1H), 7.18 (d, J = 9.20 Hz, 2H), 6.85 (d, J = 8.80 Hz, 2H), 5.19 (d, J = 8.00 Hz, 1H), 3.86 (t, J = 4.60 Hz, 4H), 3.82 - 3.77 (m, 1H), 3.12 (t, J = 5.00 Hz, 4H), 2.04 - 1.50 (m, 3H), 0.90 (d, J = 6.40 Hz, 3H), 0.8 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfonamido) pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.99 (d, J = 8.00 Hz, 2H), 7.68 (s, 1H), 7.66 (d, J = 4.00 Hz, 2H), 7.10 (d, J = 12.4 Hz, 2H), 6.79 (d, J = 12.0 Hz, 2H), 5.70 (d, J = 8.40 Hz, 1H), 3.92 - 3.98 (m, 1H), 3.85 (t, J = 4.80 Hz, 4H), 3.09 (t, J = 4.80 Hz, 4H), 1.67 - 1.54 (m, 3H), 0.89 (d, J = 6.00 Hz, 3H), 0.79 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(3-nitrophenylsulfonamido) pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.70 (s, 1H), 8.26 (d, J = 8.00 Hz, 1H), 8.0 (d, J = 8.20 Hz, 1H), 7.95 (s, 1H), 7.61 (t, J = 8.00 Hz, 1H), 7.12 (d, J = 8.80 Hz, 2H), 6.73 (d, J = 9.20 Hz, 2H)), 6.15 (d, J = 8.80 Hz, 1H), 4.07 - 4.03 (m, 1H), 3.85 (t, J = 4.60 Hz, 4H), 3.08 (t, J = 4.60 Hz, 4H), 1.72 - 1.67 (m, 1H), 1.60 - 1.56 (m, 2H), 0.90 (d, J = 6.40 Hz, 3H), 0.84 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(naphthalene-1-sulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.82 (d, J = 8.40 Hz, 1H), 8.38 (dd, J = 0.80, 7.60 Hz, 1H), 8.13 (s, 1H), 8.09 (d, J = 8.00 Hz, 1H), 7.99 (d, J = 8.00 Hz, 1H), 7.76 - 7.65 (m, 2H), 7.55 (t, J = 7.80 Hz, 1H), 7.09 - 7.06 (m, 2H), 6.79 - 6.76 (m, 2H), 6.07 (d, J = 7.20 Hz, 1H), 3.95 - 3.90 (m, 5H), 3.13 (t, J = 4.60 Hz, 4H), 1.65 - 1.61 (m, 1H), 1.51 - 1.44 (m, 2H), 0.76 (d, J = 6.00 Hz, 3H), 0.50 (d, J = 6.80 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(naphthalene-2-sulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 7.96 (s, 1H), 7.80 - 7.81 (m, 4H), 7.62 - 7.52 (m, 2H), 7.08 - 7.05 (m, 2H), 6.68 - 6.64 (m, 2H), 5.70 (d, J = 7.60 Hz, 1H), 3.97 - 3.91 (m, 1H), 3.83 (t, J = 4.80 Hz, 4H), 3.04 (t, J = 4.80 Hz, 4H), 1.63 - 1.48 (m, 3H), 0.81 (d, J = 6.40 Hz, 3H), 0.63 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(phenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.89 (d, J = 7.20 Hz, 2H), 7.75 (s, 1H), 7.56 (t, J = 7.40 Hz, 1H), 7.49 (t, J = 7.40 Hz, 2H), 7.24 (d, J = 9.20 Hz, 2H), 6.82 (d, J = 9.20 Hz, 2H), 5.20 (d, J = 7.20 Hz, 2H)), 3.85 (t, J = 4.80 Hz, 4H), 3.81 - 3.77 (m, 1H), 3.10 (t, J = 4.80 Hz, 4H), 1.66 - 1.46 (m, 3H), 0.85 (d, J = 6.00 Hz, 3H), 0.69 (d, J = 6.00 Hz, 3H)
( S )-Benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate
1H-NMR (400 MHz, CDCl3) δ 7.50 (s, 1H), 7.42 - 7.31 (m, 7H), 6.88 - 6.84 (m, 2H), 5.01 (d, J = 8.00 0Hz, 1H), 4.27 (d, J = 3.20 Hz, 2H), 3.86 - 3.81 (m, 5H), 3.12 (t, J = 4.80 Hz, 4H), 1.74 - 1.60 (m, 2H), 1.54 - 1.47 (m, 1H), 0.93 (d, J = 6.40 Hz, 3H), 0.90 (d, J = 6.40 Hz, 3H)
( S )-2-(4-Methoxyphenylsulfonamido)-4-methyl- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.83 - 7.79 (m, 2H), 7.26 - 7.22 (m, 2H), 6.89 - 6.86 (m, 2H), 6.80-6.76 (m, 2H), 5.60 (d, J = 7.60 Hz, 1H), 3.87 - 3.81 (m, 5H), 3.76 (s, 3H), 3.08 (t, J = 5.40 Hz, 4H), 1.63 - 1.58 (m, 2H), 1.51 - 1.47 (m, 1H), 0.85 (d, J = 6.00 Hz, 3H), 0.70 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(thiophene-2-sulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.73 (s, 1H), 7.65 (dd, J = 1.20, 4.00 Hz, 1H), 7.58 (dd, J = 1.20, 4.80 Hz, 1H), 7.30 - 7.27 (m, 2H), 7.05 (dd, J = 3.60, 5.20 Hz, 1H), 6.85 - 6.81 (m, 2H), 5.34 (s, 1H), 3.91 - 3.84 (m, 5H), 3.11 (t, J = 5.00 Hz, 4H), 1.72 - 1.51 (m, 3H), 0.89 (d, J = 6.00 Hz, 3H), 0.79 (d, J = 6.00 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.23 - 8.21 (m, 2H), 8.03 - 8.00 (m, 2H), 7.12 (d, J = 8.80 Hz, 2H), 6.79 (d, J = 9.20 Hz, 2H), 5.49 (d, J = 8.80 Hz, 1H), 3.91 - 3.84 (m, 5H), 3.10 (t, J = 4.80 Hz, 4H), 1.76 - 1.70 (m, 1H), 1.61 - 1.58 (m, 3H), 0.93 (d, J = 6.80 Hz, 3H), 0.87 (d, J = 6.80 Hz, 3H)
( S )-2-(4-Isopropylphenylsulfonamido)-4-methyl- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.81 - 7.78 (m, 3H), 7.31 (d, J = 8.40 Hz, 2H), 7.26 - 7.21 (m, 2H), 6.82 - 6.78 (m, 2H), 5.17 (d, J = 6.40 Hz, 1H), 3.85 (t, J = 4.00 Hz, 4H), 3.79 - 3.77 (m, 1H), 3.09 (t, J = 4.80 Hz, 4H), 2.94 - 2.87 (m, 1H), 1.68 - 1.44 (m, 3H), 1.19 (d, J = 6.80 Hz, 6H), 0.85 (d, J = 6.00 Hz, 3H), 0.67 (d, J = 6.00 Hz, 3H)
( S )-2-(Biphenyl-4-ylsulfonamido)-4-methyl- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.94 (d, J = 8.20 Hz, 2H), 7.87 (brs, 1H), 7.59 - 7.64 (m, 2H), 7.37 - 7.49 (m, 5H), 7.15 - 7.20 (m, 2H), 6.72 (d, J = 9.00 Hz, 2H), 5.48 - 5.60 (m, 1H), 3.87 - 3.95 (m, 1H), 3.79 - 3.85 (m, 4H), 2.98 - 3.05 (m, 4H), 1.62 - 1.69 (m, 2H), 1.51 - 1.60 (m, 1H), 0.88 (d, J = 5.80 Hz, 3H), 0.76 (d, J = 5.80 Hz, 3H)
( S )-4-(Benzyloxy)- N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.76 - 7.73 (m, 2H), 7.41 - 7.32 (m, 5H), 7.03 - 6.99 (m, 2H), 5.55 (d, J = 10.0 Hz, 1H), 5.11 (s, 2H), 4.22 - 4.17 (m, 1H), 3.78 - 3.39 (m, 13H), 3.22 - 3.06 (m, 3H), 1.97 - 1.90 (m, 1H), 1.48 - 1.33 (m, 2H), 0.92 (d, J = 4.00 Hz, 3H), 0.89 (d, J = 4.80 Hz, 3H)
( S )-4-Hydroxy- N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 7.65 (d, J = 8.80 Hz, 2H), 6.83 (d, J = 8.80 Hz, 2H), 5.65 (d, J = 9.60 Hz, 1H), 4.31 - 4.26 (m, 1H), 3.84 - 3.19 (m, 16H), 1.99 - 1.93 (m, 1H), 1.53 - 1.52 (m, 2H), 0.93 (t, J = 6.20 Hz, 6H)
( S )-Benzyl 4-( N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoate
1H-NMR (400 MHz, CDCl3) δ 8.19 - 8.16 (m, 2H), 7.92 - 7.89 (m, 2H), 7.45-7.34 (m, 5H), 5.76 (d, J = 9.20 Hz, 1H), 5.37 (s, 2H), 4.34 - 4.28 (m, 1H), 3.82 - 3.76 (m, 1H), 3.68 - 3.63 (m, 1H), 3.58 - 3.07 (m, 14H), 1.97 - 1.90 (m, 1H), 1.50 - 1.34 (m, 2H), 0.94 (d, J = 6.40 Hz, 3H), 0.91 (d, J = 6.80 Hz, 3H)
( S )- tert -Butyl 3-(4-methylphenylsulfonamido)-4-morpholino-4-oxobutanoate
1H-NMR (400 MHz, CDCl3) δ 7.72 (d, J = 8.40 Hz, 2H), 7.31 (d, J = 7.60 Hz, 2H), 5.89 (d, J = 9.60 Hz, 1H), 4.55 - 4.498 (m, 1H), 3.62 - 3.28 (m, 8H), 2.55 - 2.40 (m, 4H), 1.41 (m, 9H)
( S )-4-Methyl- N -(1-morpholino-1-oxo-3-phenylpropan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.68 (d, J = 4.80 Hz, 2H), 7.23 - 7.29 (m, 5H), 7.11 - 7.16 (m, 2H), 5.88 (d, J = 9.60 Hz, 1H), 4.29 - 4.35 (m, 1H), 3.22 - 3.34 (m, 3H), 3.05 - 3.14 (m, 2H), 2.90 - 2.98 (m, 2H), 2.74 - 2.81 (m, 1H), 2.55 - 2.61 (m, 2H), 2.40 (s, 3H)
( S )- N -(3-hydroxy-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.40 Hz, 2H), 7.32 (d, J = 8.4 Hz, 2H), 6.00 (d, J = 8.80 Hz, 1H), 4.19 - 4.24 (m, 1H), 3.52 - 3.68 (m, 4H), 3.34 - 3.49 (m, 6H), 2.82 (q, J = 4.30 Hz, 1H), 2.44 (s, 3H)
( S )-4-Methyl- N -(3-methyl-1-morpholino-1-oxobutan-2-yl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.69 (d, J = 8.40 Hz, 2H), 7.29 (d, J = 8.40 Hz, 2H), 5.66 (d, J = 9.20 Hz, 1H), 3.81 (q, J = 4.80 Hz, 1H), 3.51 - 3.58 (m, 2H), 3.24 - 3.35 (m, 5H), 3.10 - 3.17 (m, 1H), 2.42 (s, 3H), 1.76 - 1.84 (m, 1H), 1.02 (d, J = 6.80 Hz, 3H), 0.88 (d, J = 6.80 Hz, 3H)
( R )- N -(3-mercapto-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 7.76 (d, J = 8.00 Hz, 2H), 7.33 (d, J = 8.00 Hz, 2H), 5.95 (d, J = 9.60 Hz, 1H), 4.48 - 4.53 (m, 1H), 3.54 - 3.63 (m, 2H), 3.30 - 3.45 (m, 6H), 2.95 (dd, J = 7.00, 13.8 Hz, 1H), 2.84 (dd, J = 6.20, 14.2 Hz, 1H), 2.44 (s, 3H)
(2 S , 3 S )-3-Hydroxy-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)butanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 8.44 (s, 1H), 7.77 (d, J = 7.20 Hz, 2H), 7.28 - 7.30 (m, 3H), 6.82 (d, J = 8.80 Hz, 2H), 5.95 (d, J = 7.20 Hz, 1H), 4.38 - 4.40 (m, 1H), 3.84 (t, J = 4.60 Hz, 4H), 3.77 (dd, J = 2.20, 6.60 Hz, 1H), 3.08 - 3.10 (m, 5H), 2.39 (s, 3H), 0.96 (d, J = 6.40 Hz, 3H)
(2 S ,3 S )-3-Methyl-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.57 (s, 1H), 7.84 (d, J = 7.60 Hz, 1H), 7.61 (d, J = 8.40 Hz, 2H), 7.18 (d, J = 8.00 Hz, 2H), 7.11 (d, J = 9.20 Hz, 2H), 6.80 (d, J = 8.80 Hz, 2H), 3.71 (t, J = 4.80 Hz, 4H), 3.57 (t, J = 7.60 Hz, 1H), 3.00 (t, J = 4.60 Hz, 4H), 2.20 (s, 3H), 1.50 - 1.63 (m, 2H), 1.08 - 1.12 (m, 1H), 0.76 - 0.79 (m, 6H)
( S )-2-(4-Methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.63 (s, 1H), 8.00 (s, 1H) 7.66 (d, J = 7.60 Hz, 2H), 7.23 - 7.29 (m, 4H), 6.84 (d, J = 8.80 Hz, 2H), 3.87 (q, J = 6.80 Hz, 1H), 3.71 (t, J = 4.60 Hz, 4H), 3.01 (t, J = 4.40 Hz, 4H), 2.29 (s, 3H), 1.12 (d, J = 7.20 Hz, 3H)
( S )-2-(4-Methylphenylsulfonamido)-4-(methylthio)- N -(4-morpholinophenyl)butanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.06 (s, 1H), 8.42 (s, 1H), 8.03 (d, J = 8.00 Hz, 2H), 7.63 (d, J = 8.40 Hz, 2H), 7.59 (d, J = 9.20 Hz, 2H), 7.21 (d, J = 8.80 Hz, 2H), 4.26 - 4.29 (m, 1H), 4.09 (t, J = 4.40 Hz, 4H), 3.76 (s, 3H), 3.39 (t, J = 4.60 Hz, 4H), 2.74 - 2.87 (m, 2H), 2.33 (s, 3H), 2.05 - 2.25 (m, 2H)
( S )-3-(1 H -indol-2-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl) propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.75 (s, 1H), 9.64 (s, 1H), 8.05 (s, 1H), 7.50 (d, J = 8.00 Hz, 2H), 7.39 (d, J = 7.60 Hz, 1H), 7.27 (d, J = 8.40 Hz, 1H), 7.18 (d, J = 9.20 Hz, 2H), 7.09 (d, J = 8.40 Hz, 2H), 7.06 (d, J = 2.00 Hz, 1H), 7.02 (t, J = 7.40 Hz, 1H), 6.91 (t, J = 7.20 Hz, 1H), 6.81 (d, J = 8.80 Hz, 2H), 3.99 - 4.06 (m, 1H), 3.71 (t, J = 4.80 Hz, 4H), 2.99 - 3.05 (m, 5H), 2.79 - 2.85 (m, 1H), 2.18 (s, 3H)
( S )-3-(1-Methyl-1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl) propanamide
1H-NMR (400 MHz, CDCl3) δ 8.04 (s, 1H), 7.48 (d, J = 8.20 Hz, 2H), 7.17 - 7.31 (m, 5H), 7.06 (d, J = 8.20 Hz, 2H), 7.00 (dt, J = 1.10, 7.20 Hz, 1H), 6.82 (d, J = 9.00 Hz, 2H), 6.76 (s, 1H), 5.17 (d, J = 6.20 Hz, 1H), 4.01 (q, J = 6.20 Hz, 1H), 3.82 - 3.87 (m, 3H), 3.67 (s, 2H), 3.17 (dd, J = 2.93, 6.46 Hz, 1H), 3.07 - 3.12 (m, 2H), 2.34 (s, 3H)
( S )-2-(4-Methylphenylsulfonamido)- N -(4-morpholinophenyl)-3-phenylpropanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.64 (s, 1H), 8.11 (s, 1H), 7.48 (d, J = 7.60 Hz, 2H), 7.12 - 7.20 (m, 9H), 6.81 (d, J = 8.40 Hz, 2H), 4.03 - 4.05 (m, 1H), 3.71 (t, J = 4.40 Hz, 4H), 3.01 (t, J = 4.40 Hz, 4H), 2.85 - 2.90 (m, 1H), 2.70 - 2.73 (m, 1H), 2.24 (s, 3H)
( S )-Benzyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate
1H-NMR (400 MHz, CDCl3) δ 7.66 - 7.73 (m, 2H), 7.30 - 7.38 (m, 3H), 7.15 - 7.24 (m, 4H), 5.20 (d, J = 10.1 Hz, 1H), 4.79 - 4.89 (m, 2H), 3.98 (ddd, J = 6.20, 8.30, 10.0 Hz, 1H), 2.39 (s, 3H), 1.72 - 1.85 (m, 1H), 1.43 - 1.55 (m, 2H), 0.87 (dd, J = 6.60, 7.80 Hz, 6H)
( S )-Benzyl 4-methyl-2-(4-methylbenzamido)pentanoate
1H-NMR (400 MHz, CDCl3) δ 7.69 (d, J = 8.00 Hz, 2H), 7.39 - 7.32 (m, 5H), 7.24 (d, J = 8.40 Hz, 2H), 6.48 (d, J = 7.60 Hz, 1H), 5.20 (d, J = 1.20 Hz, 2H), 4.93 - 4.87 (m, 1H), 2.40 (s, 3H), 1.80 - 1.62 (m, 3H), 0.97 (d, J = 6.00 Hz, 3H), 0.95 (d, J = 6.00 Hz, 3H)
( S )-Benzyl 2-(4- tert -butylbenzamido)-4-methylpentanoate
1H-NMR (400 MHz, CDCl3) δ 7.74 - 7.72 (m, 2H), 7.52 - 7.44 (m, 2H), 7.37 - 7.31 (m, 5H), 6.49 (d, J = 8.40 Hz, 1H), 5.19 (s, 2H), 4.94 - 4.88 (m, 1H), 1.78 - 1.63 (m, 3H), 1.33 (s, 9H), 0.97 (d, J = 6.00 Hz, 3H), 0.94 (d, J = 5.60 Hz, 3H)
( S )-Benzyl 2-(benzo[ d ][1,3]dioxole-5-carboxamido)-4-methylpentanoate
1H-NMR (400 MHz, CDCl3) δ 7.71 (dd, J = 2.00, 8.00 Hz, 1H), 7.51 (d, J = 2.00 Hz, 1H), 7.38 - 7.33 (m, 5H), 6.86 (d, J = 8.40 Hz, 1H), 6.06 (s, 2H), 5.16 (d, J = 1.20 Hz, 2H), 3.56 - 3.52 (m, 1H), 1.78 - 1.73 (m, 1H), 1.63 - 1.56 (m, 1H), 1.48 - 1.41 (m, 1H), 0.93 (d, J = 6.40 Hz, 3H), 0.91 (d, J = 6.80 Hz, 3H)
( S )-Benzyl 2-(4-( tert -butoxycarbonylamino)benzamido)-4-methylpentanoate
1H-NMR (400 MHz, CDCl3) δ 7.75 - 7.72 (m, 2H), 7.43 (d, J = 8.40 Hz, 2H), 7.39 - 7.31 (m, 5H), 6.61 (s, 1H), 6.43 (d, J = 8.40 Hz, 1H), 5.19 (d, J = 2.00 Hz, 2H), 4.92 - 4.86 (m, 1H), 1.78 - 1.62 (m, 3H), 0.97 (d, J = 6.00 Hz, 3H), 0.95 (d, J = 6.40 Hz, 3H)
( S )-Benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate
1H-NMR (400 MHz, CDCl3) δ 7.91 - 7.89 (m, 2H), 7.68 - 7.54 (m, 3H), 7.38 - 7.31 (m, 5H), 5.97 (d, J = 8.00 Hz, 1H), 5.14 (s, 2H), 4.61 - 4.56 (m, 1H), 3.46 - 3.40 (m, 2H), 2.71 - 2.66 (m, 2H), 1.64 - 1.50 (m, 3H), 0.90 (d, J = 5.60 Hz, 6H)
( S )- N -(4-(4-methoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.54 (brs, 1H), 7.75 (t, J = 7.60 Hz, 4H), 7.26 (d, J = 8.20 Hz, 2H), 6.99 (d, J = 0.70 Hz, 1H), 6.95 (d, J = 8.20 Hz, 2H), 5.19 (d, J = 7.00 Hz, 1H), 3.91 (d, J = 5.00 Hz, 1H), 3.84 (d, J = 0.70 Hz, 3H), 2.32 (s, 3H), 1.53 - 1.63 (m, 2H), 1.43 - 1.51 (m, 1H), 0.84 (d, J = 5.80 Hz, 3H), 0.68 (d, J = 5.80 Hz, 3H)
( S )-1-(4-Methyl-1-morpholino-1-oxopentan-2-yl)-3-phenylurea
1H-NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 7.26 - 7.17 (m, 4H), 6.94 - 6.90 (m, 1H), 6.72 (d, J = 8.80 Hz, 1H), 5.03 - 4.97 (m, 1H), 3.81 - 3.57 (m, 8H), 1.84 - 1.77 (m, 1H), 1.61 - 1.43 (m, 2H), 0.90 (d, J = 3.60 Hz, 3H), 0.87 (d, J = 7.20 Hz, 3H)
( S )-4- tert -Butyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 8.40 (s, 1H), 7.81 (d, J = 8.00 Hz, 2H), 7.45 (d, J = 8.80 Hz, 2H), 4.82 - 4.73 (m, 1H), 3.53 - 3.42 (m, 8H), 1.74 - 1.50 (m, 3H), 1.28 (s, 9H), 0.89 (d, J = 6.80 Hz, 6H)
( S )- N -(4-Methyl-1-morpholino-1-oxopentan-2-yl)-3-(phenylsulfonyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 8.30 (d, J = 8.80 Hz, 1H), 7.88 - 7.86 (m, 2H), 7.75 (t, J = 8.00 Hz, 1H), 7.65 (d, J = 8.00 Hz, 2H), 4.66 - 4.61 (m, 1H), 3.52 - 3.25 (m, 10H), 2.46 - 2.42 (m, 2H), 1.52 - 1.46 (m, 1H), 1.38 - 1.33 (m, 2H), 0.82 (d, J = 6.60 Hz, 6H)
( S )-4- tert -Butyl- N -(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide
1H-NMR (400 MHz, MeOD) δ 7.81(d, J = 8.00 Hz, 2H), 7.51 (t, J = 8.80 Hz, 2H), 7.45 (d, J = 8.80 Hz, 2H), 6.94 (d, J = 8.80 Hz, 2H), 4.85 - 4.81 (m, 1H), 3.82 (t, J = 5.00 Hz, 3H), 3.10 (t, J = 4.80 Hz, 3H), 1.82 - 1.62 (m, 3H), 1.28 (s, 9H), 1.03 (d, J = 6.60 Hz, 6H)
( S )- N -(4-Methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzo[ d ][1,3]dioxole-5-carboxamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.84 (s, 1H), 8.35 (d, J = 7.60 Hz, 1H), 7.52 - 7.44 (m, 4H), 6.97 (d, J = 8.40 Hz, 1H), 6.87 (d, J = 9.20 Hz, 2H), 6.08 (d, J = 2.40 Hz, 2H), 4.60 - 4.54 (m, 1H), 3.71 (d, J = 4.80 Hz, 4H), 3.02 (t, J = 4.80 Hz, 4H), 1.74 - 1.50 (m, 3H), 0.92 (d, J = 6.80 Hz, 3H), 0.89 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl- N -(4-morpholinophenyl)-2-(3-(phenylsulfonyl)propanamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.69 - 8.63 (m, 1H), 7.87 (d, J = 7.20 Hz, 2H), 7.71 - 7.32 (m, 5H), 7.18 - 6.60 (m, 3H), 4.59 - 4.55 (m, 1H), 3.82 (t, J = 5.00 Hz, 3H), 3.54 - 3.48 (m, 2H), 3.06 (t, J = 4.80 Hz, 3H), 2.75 - 2.73 (m, 2H), 1.85 - 1.56 (m, 3H), 0.89 (d, J = 6.2 Hz, 6H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.44 (s, 1H), 10.78 (s, 1H), 8.51 (brs, 1H), 7.82 - 7.80 (d, J = 8.50 Hz, 2H), 7.47 - 7.37 (m, 6H), 7.28 - 7.26 (d, J = 8 .00 Hz), 7.08 - 6.90 (m, 5H), 4.32 (brs, 1H), 3.79 (s, 3H), 3.33 (s, 2H), 3.11 - 3.07 (dd, J = 14.5, 6.00 Hz, 1H), 2.90 - 2.85 (dd, J = 14.0, 8.50 Hz, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.3 (s, 1H), 10.7 (s, 1H), 8.24 - 8.22 (d, J = 8.50 Hz, 1H), 7.95 - 7.93 (d, J = 8.50 Hz, 1H), 7.50 - 7.48 (d, J = 8.50 Hz, 2H), 7.15 - 7.09 (m, 4H), 6.97 - 6.95 (d, J = 8.00 Hz, 1H), 6.74 - 6.58 (m, 6H), 4.01 - 3.96 (q, J = 7.50 Hz, 1H), 3.47 (s, 3H), 2.79 - 2.74 (dd, J = 14.2, 7.00 Hz, 1H), 2.56 - 2.51 (dd, J = 14.5, 8.00 Hz, 1H), 1.86 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(2-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.86 - 7.83 (m, 2H), 7.33 - 7.29 (m, 3H), 7.20 - 7.14 (m, 4H), 7.01 - 6.95 (m, 2H), 6.91 (d, J = 2.40 Hz, 4H), 6.80 - 6.78 (m, 2H), 5.38 (d, J = 5.60 Hz, 1H), 4.00 - 3.95 (m, 1H), 3.83 (t, J = 4.60 Hz, 4H), 3.27 - 3.14 (m, 2H), 3.07 (t, J = 5.00 Hz, 4H), 2.23 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(3-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.76 (s, 1H), 9.70 (s, 1H), 8.11 (s, 1H), 7.45 - 7.39 (m, 3H), 7.28 - 7.19 (m, 5H), 7.06 - 7.00 (m, 2H), 6.93 - 6.89 (m, 1H), 6.81 (d, J = 8.80 Hz, 2H), 4.09 - 4.07 (m, 1H), 3.71 (t, J = 4.80 Hz, 4H), 3.05 - 2.99 (m, 5H), 2.85 - 2.79 (m, 1H), 2.14 (s, 3H)
( S )-2-(3,5-Dimethylphenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4 morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.77 (s, 1H), 9.71 (s, 1H), 8.04 (s, 1H), 7.42 (d, J = 8.00 Hz, 1H), 7.28 - 7.22 (m, 5H), 7.07 - 7.00 (m, 3H), 6.92 (t, J = 7.40 Hz, 1H), 6.82 (d, J = 9.20 Hz, 2H), 4.11 - 4.07 (m, 1H), 3.71 (t, J = 4.80 Hz, 4H), 3.05 - 2.99 (m, 5H), 2.85 - 2.80 (m, 1H), 2.12 (s, 6H)
( S )-2-(4-Fluorophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.77 (d, J = 2.00 Hz, 1H), 9.75 (s, 1H), 8.26 (s, 1H), 7.62 - 7.59 (m, 2H), 7.46 (d, J = 8.00 Hz, 1H), 7.28 - 7.22 (m, 3H), 7.09 - 7.01 (m, 4H), 6.93 (t, J = 7.40 Hz, 1H), 6.85 - 6.81 (m, 2H), 4.10 (s, 1H), 3.72 (t, J = 4.80 Hz, 4H), 3.07 - 3.01 (m, 5H), 2.89 - 2.83 (m, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfon-amido)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.77 (d, J = 1.60 Hz, 1H), 9.79 (s, 1H), 8.55 (s, 1H), 7.72 (d, J = 8.80 Hz, 2H), 7.57 (d, J = 8.40 Hz, 2H), 4.47 (d, J = 8.00 Hz, 1H), 7.25 (d, J = 7.60 Hz, 1H), 7.19 (d, J = 9.20 Hz, 2H), 7.11 (d, J = 2.40 Hz, 1H), 7.02 (t, J = 7.60 Hz, 1H), 6.92 (t, J = 7.40 Hz, 1H), 6.81 (d, J = 9.20 Hz, 2H), 4.14 (s, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.08 - 2.99 (m, 5H), 2.92 - 2.86 (m, 1H)
( S )-3-(5-Hydroxy-1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.45 (d, J = 2.00 Hz, 1H), 9.63 (s, 1H), 8.54 (s, 1H), 8.02 (s, 1H), 7.53 (d, J = 8.00 Hz, 2H), 7.18 (d, J = 9.20 Hz, 2H), 7.11 (d, J = 8.20 Hz, 2H), 7.07 (d, J = 8.40 Hz, 1H), 6.97 (d, J = 2.40 Hz, 1H), 6.81 (d, J = 8.00 Hz, 2H), 6.77 (d, J = 2.00 Hz, 1H), 6.57 (dd, J = 2.00, 8.40 Hz, 1H), 4.09 - 4.06 (s, 1H), 3.72 (t, J = 4.80 Hz, 4H), 3.01 (t, J = 5.00 Hz, 4H), 2.96 - 2.91 (m, 1H), 2.76 - 2.70 (m, 1H), 2.23 (s, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 8.19 (brs, 1H), 7.67 - 7.71 (m, 2H), 7.48 (d, J = 7.83 Hz, 1H), 7.34 (d, J = 8.22 Hz, 1H), 7.25 (d, J = 7.83 Hz, 2H), 7.18 (dt, J = 1.17, 7.63 Hz, 1H), 7.07 - 7.12 (m, 1H), 7.06 (d, J = 1.96 Hz, 1H), 5.92 (d, J = 9.78 Hz, 1H), 4.42 (dt, J = 5.28, 9.88 Hz, 1H), 3.19 - 3.34 (m, 4H), 3.08 - 3.15 (m, 1H), 2.86 - 2.98 (m, 2H), 2.75 (m, 1H), 2.62 - 2.70 (m, 1H), 2.50 - 2.56 (m, 1H), 2.39 (s, 3H), 2.19 (m, 1H).
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(5-morpholinothiazol-2-yl)propan amide
1H-NMR (400 MHz, CDCl3) δ 8.20 - 8.24 (m, 1H), 7.54 (d, J = 8.22 Hz, 2H), 7.20 (d, J = 8.22 Hz, 2H), 7.01 - 7.10 (m, 3H), 6.91 (t, J = 7.43 Hz, 1H), 6.86 (d, J = 2.35 Hz, 1H), 6.48 (s, 1H), 6.17 - 6.23 (m, 1H), 4.27 (d, J = 6.65 Hz, 1H), 3.78 (t, J = 4.70 Hz, 4H), 3.16 (d, J = 6.65 Hz, 2H), 2.87 - 2.99 (m, 4H), 2.25 (s, 3H)
( S )-2-(2,4-Dimethylphenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.75 (s, 1H), 9.58 (s, 1H), 7.98 (s, 1H), 7.54 (d, J = 8.00 Hz, 1H), 7.38 (d, J = 8.00 Hz, 1H), 7.28 (d, J = 8.40 Hz, 1H), 7.19 (d, J = 9.20 Hz, 2H), 7.08 (d, J = 2.40 Hz, 1H), 7.02 (t, J = 7.40 Hz, 1H), 6.90 - 6.81 (m, 5H), 4.05 - 4.03 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.04 - 3.00 (m, 5H), 2.90 - 2.85 (m, 1H), 2.39 (s, 3H), 2.15 (s, 3H)
3-(3-Ethoxy-2-(4-methylphenylsulfonamido)-3-oxopropyl)-1 H -indole-5-carboxylic acid
1H-NMR (400 MHz, CDCl3) δ 12.37 (s, 1H), 11.17 (s, 1H), 8.37 (d, J = 8.40 Hz, 1H), 8.01 (s, 1H), 7.68 (dd, J = 1.40, 8.60 Hz, 1H), 7.48 (d, J = 8.00 Hz, 1H), 7.35 (d, J = 8.40 Hz, 1H), 7.20 - 7.08 (m, 3H), 3.96 - 3.90 (m, 1H), 3.08 - 3.06 (m, 1H), 2.94 - 2.88 (m, 1H), 2.31 (s, 1H), 0.86 (t, J = 6.60 Hz, 3H)
( S )-2-(4-Methylphenylsulfonamido)- N -(4-morpholinophenyl)-3-(1-tosyl-1H-imidazol-4-yl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 7.84 (s, 1H), 7.71 (t, J = 8.40 Hz, 4H), 7.29 - 7.23 (m, 6H), 6.98 (s, 1H), 6.89 (d, J = 6.40 Hz, 1H), 6.83 (dt, J = 8.80 Hz, 2H), 3.99 - 3.97 (m, 1H), 3.85 (t, J = 4.80 Hz, 4H), 3.10 (t, J = 4.80 Hz, 4H), 3.01 (dd, J = 5.60, 15.2 Hz, 1H), 2.61 (dd, J = 4.80, 14.8 Hz, 1H), 2.40 (d, J = 8.40 Hz, 6H)
( S )- N -(6-((2 S ,6 R )-2,6-dimethylmorpholino)pyridin-3-yl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.14 (brs, 1H), 8.00 (d, J = 2.35 Hz, 1H), 7.86 (s, 1H), 7.62 (dd, J = 2.74, 9.00 Hz, 1H), 7.49 - 7.53 (m, 2H), 7.33 (dd, J = 3.91, 7.83 Hz, 2H), 7.20 (t, J = 7.63 Hz, 1H), 7.08 - 7.12 (m, 2H), 7.02 (t, J = 7.63 Hz, 1H), 6.96 (d, J = 1.96 Hz, 1H), 6.57 (d, J = 9.00 Hz, 1H), 5.11 (d, J = 6.26 Hz, 1H), 4.05 (q, J = 6.52 Hz, 1H), 3.97 (d, J = 11.35 Hz, 2H), 3.67 - 3.77 (m, 2H), 3.12 - 3.28 (m, 2H), 2.45 - 2.53 (m, 2H), 2.36 (s, 3H), 1.27 (d, J = 6.26 Hz, 6H)
( R )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.80 (brs, 1H), 8.27 (s, 1H), 7.97 (s, 2H), 7.45 - 7.48 (m, 2H), 7.32 (d, J = 7.83 Hz, 1H), 7.29 (d, J = 3.52 Hz, 1H), 7.22 (s, 1H), 7.13 (t, J = 7.43 Hz, 1H), 7.00 (d, J = 8.22 Hz, 2H), 6.94 (s, 1H), 6.78 - 6.81 (m, J = 9.00 Hz, 2H), 5.57 (d, J = 6.65 Hz, 1H), 4.05 (d, J = 6.65 Hz, 1H), 3.80 - 3.86 (m, 4H), 3.19 (dd, J = 6.46, 13.50 Hz, 2H), 3.05 - 3.10 (m, 4H), 2.28 (s, 3H)
( S )- N -(3-fluoro-4-morpholinophenyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, DMSO-d 6) δ 10.78 (s, 1H), 9.90 (s, 1H), 8.16 (brs, 1H), 7.51 (d, J = 8.22 Hz, 2H), 7.40 (d, J = 7.83 Hz, 1H), 7.29 (d, J = 7.83 Hz, 1H), 7.22 (dd, J = 2.15, 15.1 Hz, 1H), 7.09 (d, J = 8.61 Hz, 3H), 7.04 (t, J = 7.63 Hz, 1H), 6.89 - 6.99 (m, 3H), 4.06 (brs, 1H), 3.70 - 3.74 (m, 4H), 3.04 (dd, J = 6.85, 14.3 Hz, 1H), 2.90 - 2.94 (m, 4H), 2.85 (dd, J = 7.40, 14.4 Hz, 1H), 2.21 (s, 3H)
( S )-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.71 (brs, 1H), 9.90 (s, 1H), 8.66 (brs, 1H), 7.84 - 7.90 (m, 2H), 7.56 - 7.61 (m, 2H), 7.48 (d, J = 7.83 Hz, 1H), 7.29 - 7.35 (m, J = 9.00 Hz, 2H), 7.12 (d, J = 7.83 Hz, 1H), 7.05 - 7.08 (m, 1H), 6.87 - 6.96 (m, 2H), 6.81 - 6.86 (m, 2H), 4.13 (dd, J = 5.28, 9.19 Hz, 1H), 3.70 - 3.75 (m, 4H), 2.98 - 3.05 (m, 5H), 2.88 (dd, J = 9.78, 14.5 Hz, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.77 (brs, 1H), 9.77 (s, 1H), 8.35 (brs, 1H), 7.40 - 7.48 (m, 5H), 7.28 (d, J = 8.22 Hz, 1H), 7.19 - 7.24 (m, 2H), 7.07 - 7.11 (m, 1H), 7.04 (t, J = 7.43 Hz, 1H), 6.91 - 6.96 (m, 1H), 6.81 - 6.86 (m, 2H), 4.10 (t, J = 7.24 Hz, 1H), 3.69 - 3.75 (m, 4H), 3.00 - 3.08 (m, 5H), 2.86 (dd, J = 8.41, 14.28 Hz, 1H)
( S )-3-(1 H -indol-3-yl)-2-(4-methoxyphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6) δ 10.78 (brs, 1H), 9.67 (s, 1H), 7.99 (brs, 1H), 7.54 (d, J = 8.61 Hz, 2H), 7.41 (d, J = 7.83 Hz, 1H), 7.28 (d, J = 8.22 Hz, 1H), 7.22 (d, J = 9.00 Hz, 2H), 7.07 - 7.10 (m, 1H), 7.03 (t, J = 7.63 Hz, 1H), 6.90 - 6.95 (m, 1H), 6.81 (t, J = 9.59 Hz, 4H), 4.06 (brs, 1H), 3.70 - 3.74 (m, 4H), 3.69 (s, 3H), 2.98 - 3.07 (m, 5H), 2.80 - 2.90 (m, 1H)
( S )-3-(1 H -indol-3-yl)-2-(4-isopropylphenylsulfonamido)- N -(4 morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.09 (brs, 1H), 8.03 (s, 1H), 7.81 (s, 1H), 7.58 - 7.62 (m, 2H), 7.33 - 7.38 (m, 2H), 7.18 - 7.25 (m, 5H), 7.05 (t, J = 7.43 Hz, 1H), 6.97 (d, J = 2.35 Hz, 1H), 6.80 - 6.85 (m, J = 9.00 Hz, 2H), 5.11 (d, J = 6.26 Hz, 1H), 4.08 (d, J = 6.26 Hz, 1H), 3.83 - 3.89 (m, 4H), 3.34 (dd, J = 6.06, 14.28 Hz, 1H), 3.09 - 3.16 (m, 5H), 1.25 (dd, J = 2.35, 7.04 Hz, 6H)
( S )-3-(1 H -indol-3-yl)-2-(4-isopropylphenylsulfonamido)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.40 Hz, 2H), 7.67 (d, J = 7.60 Hz, 2H), 7.21 (t, J = 6.80 Hz, 4H), 7.04 (s, 1H), 3.98 - 3.95 (m, 1H), 2.37 (s, 1H), 2.26 (m, 3H), 1.64 - 1.49 (m, 3H), 0.85 (d, J = 6.40 Hz, 3H), 0.72 (d, J = 6.40 Hz, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-methylthiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.13 (s, 1H), 10.83 (s, 1H), 8.26 - 8.24 (d, J = 8.50 Hz, 1H), 7.45 - 7.44 (d, J = 8.00 Hz, 2H), 7.39 - 7.38 (d, J = 7.50 Hz, 1H), 7.29 - 7.27 (d, J = 8.00 Hz, 1H), 7.06 - 7.02 (m, 4H), 6.91 - 6.89 (m, 1H), 6.72 (s, 1H), 4.27 - 4.22 (m, 1H), 3.07 - 3.03 (dd, J = 14.2, 7.50 Hz, 1H), 2.86 - 2.81 (dd, J = 14.2, 8.00 Hz, 1H), 2.24 (s, 3H), 2.22 (s, 3H)
( S )- N -(benzo[ d ]thiazol-2-yl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.4 (s, 1H), 10.8 (s, 1H), 8.32 (m, 1H), 7.91 (m, 1H), 7.72 (m, 1H), 7.47 - 7.44 (m, 6H), 7.03 - 6.91 (m, 5H), 4.34 (brs, 1H), 3.11 (m, 1H), 2.91 (m, 1H), 2.08 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)propanoic acid
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.73 (brs, 1H), 10.80 (s, 1H), 8.41 - 8.39 (d, J = 8.50 Hz, 1H), 7.51 - 7.49 (d, J = 8.50 Hz, 2H), 7.42 - 7.40 (d, J = 8.00 Hz, 2H), 7.32 - 7.29 (t, J = 8.00 Hz, 2H), 7.08 - 7.03 (m, 2H), 6.94 - 6.91 (t, J = 7.50 Hz, 1H), 3.94 - 3.89 (m, 1H), 3.10 - 3.08 (dd, J = 14.5, 6.00 Hz, 1H), 2.89 - 2.84 (dd, J = 14.0, 8.50 Hz, 1H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(5-morpholinothiazol-2-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.71 (d, J = 8.00 Hz, 2H), 7.16 (d, J = 8.00 Hz, 2H), 6.95 (s, 1H), 6.35 (d, J = 10.0 Hz, 1H), 4.14 - 4.06 (m, 1H), 3.86 (t, J = 4.80 Hz, 4H), 3.13 - 3.07 (m, 4H), 2.29 (s, 3H), 1.75 - 1.70(m, 1H), 1.60 - 1.53 (m, 1H), 1.46 - 1.41 (m, 1H), 0.81 (d, J = 6.80 Hz, 6H)
( S )- N -(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 13.52 (s, 1H), 8.14 (d, J = 8.80 Hz, 1H), 7.92 - 7.88 (m, 2H), 7.68 (d, J = 8.40 Hz, 2H), 7.18 (d, J = 8.40 Hz, 2H), 7.07 - 7.04 (m, 2H), 4.36 - 4.29 (m, 1H), 3.91 (s, 3H), 2.21 (s, 3H), 1.84 - 1.79 (m, 1H), 1.72 - 1.64 (m, 1H), 1.59 - 1.54 (m, 1H), 0.89 (d, J = 6.40 Hz, 3H), 0.86 (d, J = 6.80 Hz, 1H)
( S )- N -(5-(4-methoxyphenyl)isoxazol-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 10.55 (s, 1H), 7.80 - 7.76 (m, 4H), 7.19 - 7.15 (m, 3H), 6.99 (d, J = 9.20 Hz, 2H), 6.43 (d, J = 9.20 Hz, 1H), 4.22 - 4.16 (m, 1H), 3.86 (s, 3H), 2.21 (s, 3H), 1.88 - 1.83 (m, 1H), 1.72 - 1.59 (m, 2H), 0.91 (d, J = 6.80 Hz, 3H), 0.88 (d, J = 6.40 Hz, 3H).
( S )- N -(3-(4-methoxyphenyl)isoxazol-5-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.22 (s, 1H), 7.78 (d, J = 8.40 Hz, 2H), 7.74 - 7.71 (m, 2H), 7.30 (d, J = 8.00 Hz, 2H), 6.98 - 6.94 (m, 2H), 6.56 (s, 1H), 5.40 (d, J = 7.20 Hz, 1H), 3.97 - 3.92 (m, 1H), 3.85 (s, 3H), 2.35 (s, 3H), 1.64 - 1.47 (m, 3H), 0.83 (d, J = 6.40 Hz, 3H), 0.66 (d, J = 5.60 Hz, 1H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.69 (s, 1H), 7.91 (d, J = 8.40 Hz, 2H), 7.79 (d, J = 8.40 Hz, 2H), 7.65 (d, J = 8.40 Hz, 2H), 7.29 - 7.26 (m, 2H), 7.23 (s, 1H), 5.26 (d, J = 6.80 Hz, 1H), 3.97 - 3.92 (m, 1H), 2.33 (s, 3H), 1.67 - 1.45 (m, 3H), 0.83 (d, J = 6.40 Hz, 3H), 0.65 (d, J = 6.40 Hz, 3H)
( S )- N -(4-(3,4-dimethoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.74 (s, 1H), 7.76 (d, J = 7.60 Hz, 2H), 7.38 - 7.34 (m, 2H), 7.26 (d, J = 6.80 Hz, 2H), 7.01 (s, 1H), 6.90 (d, J = 8.00 Hz, 1H), 5.40 (d, J = 6.80 Hz, 1H), 4.19 - 4.10 (m, 1H), 3.95 (s, 3H), 3.90 (s, 3H), 2.32 (s, 3H), 1.60 - 1.42 (m, 3H), 0.80 (d, J = 6.00 Hz, 3H), 0.63 (d, J = 5.60 Hz, 3H)
( S )- N -(4-(2-bromo-4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.62 (s, 1H), 7.78 - 7.75 (m, 4H), 7.26 (s, 1H), 7.10 - 7.05 (m, 3H), 5.31 (d, J = 7.60 Hz, 1H), 3.95 - 3.92 (m, 1H), 2.32 (s, 3H), 1.64 - 1.46 (m, 3H), 0.82 (d, J = 6.40 Hz, 3H), 0.66 (d, J = 6.00 Hz, 3H).
( S )-4-(2-Aminothiazol-4-yl)phenyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate
1H-NMR (400 MHz, CDCl3) δ 7.79 (d, J = 7.60 Hz, 2H), 7.67 (d, J = 7.60 Hz, 2H), 7.29 (d, J = 7.20 Hz, 2H), 6.68 (d, J = 7.60 Hz, 2H), 6.65 (s, 1H), 5.53 (d, J = 9.20 Hz, 1H), 5.27 (s, 2H), 4.16 - 4.11 (m, 1H), 2.41 (m, 3H), 1.90 - 1.87 (m, 1H), 1.63 - 1.60 (m, 1H), 1.27 - 1.24 (m, 1H), 0.94 (s, 6H)
( S )- N -(4-(4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.58 (s, 1H), 7.79 - 7.76 (m, 3H), 7.28 - 7.26 (m, 2H), 7.11 - 7.06 (m, 2H), 5.20 (d, J = 6.80 Hz, 2H), 5.27 (s, 2H), 3.93 - 3.91 (m, 1H), 2.41 (m, 3H), 1.66 - 1.46 (m, 3H), 0.83 (d, J = 6.40 Hz, 3H), 0.65 (d, J = 6.40 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(4-(trifluoromethoxy)phenyl)thiazol-2-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.60 (s, 1H), 7.83 (d, J = 8.80 Hz, 2H), 7.79 (d, J = 8.00 Hz, 2H), 7.29 - 7.23 (m, 4H), 7.13 (s, 1H), 5.21 (d, J = 6.80 Hz, 1H), 3.93 (s, 1H), 2.33 (m, 3H), 1.65 - 1.48 (m, 3H), 0.83 (d, J = 6.40 Hz, 3H), 0.64 (d, J = 6.00 Hz, 3H)
( S )- N -(4-(4-hydroxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.72 (d, J = 8.00 Hz, 2H), 7.64 (d, J = 8.80 Hz, 2H), 7.20 (d, J = 8.00 Hz, 2H), 6.93 (s, 1H), 6.88 (d, J = 8.40 Hz, 2H), 3.97 - 3.93 (m, 1H), 2.25 (s, 3H), 1.65 - 1.51 (m, 3H), 0.88 (d, J = 6.40 Hz, 3H), 0.75 (d, J = 6.00 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-p-tolylthiazol-2-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.40 Hz, 2H), 7.67 (d, J = 7.60 Hz, 2H), 7.21 (t, J = 6.80 Hz, 4H), 7.04 (s, 1H), 3.98 - 3.95 (m, 1H), 2.37 (s, 1H), 2.26 (m, 3H), 1.64 - 1.49 (m, 3H), 0.85 (d, J = 6.40 Hz, 3H), 0.72 (d, J = 6.40 Hz, 3H)
( S )- N -(4-(4-(( S )-1-methoxypropan-2-yloxy)phenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 9.97 (s, 1H), 7.74 (d, J = 8.40 Hz, 2H), 7.69 (d, J = 8.80 Hz, 2H), 7.23 (d, J = 8.00 Hz, 2H), 6.97 (s, 1H), 6.95 (d, J = 9.20 Hz, 2H), 5.71 (d, J = 7.60 Hz, 1H), 4.58 - 4.54 (m, 1H), 4.00 - 3.94 (m, 1H), 3.60 - 3.46 (m, 2H), 3.40 (s, 3H), 2.28 (s, 3H), 1.56 - 1.40 (m, 3H), 1.31 (d, J = 6.00 Hz, 3H), 0.78 (d, J = 6.00 Hz, 3H), 0.66 (d, J = 5.60 Hz, 3H)
( S )-4-Methyl-2-(4-methylphenylsulfonamido)- N -(4-(4-morpholinophenyl)thiazol-2-yl)pentanamide
1H-NMR (400 MHz, CDCl3) δ 8.28 (dd, J = 9.00, 11.4 Hz, 4H), 7.19 (d, J = 8.40 Hz, 2H), 6.95 (t, J = 4.60 Hz, 3H), 4.13 - 3.95 (m, 1H), 3.89 (t, J = 4.80 Hz, 3H), 3.21 (t, J = 5.00 Hz, 3H), 2.25 (s, 3H), 1.67 - 1.64 (m, 1H), 1.55 - 1.51 (m, 2H), 0.88 (d, J = 6.80 Hz, 3H), 0.75 (d, J = 6.40 Hz, 3H)
( S )-Methyl 4-(2-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido)thiazol-4-yl)benzoate
1H-NMR (400 MHz, CDCl3) δ 10.05 (s, 1H), 8.18 (d, J = 8.00 Hz, 2H), 7.93 (d, J = 8.40 Hz, 2H), 7.76 (d, J = 8.00 Hz, 2H), 7.26 (s, 1H), 7.20 (d, J = 8.00 Hz, 2H), 5.63 (d, J = 8.00 Hz, 1H), 4.12 - 4.09 (m, 1H), 3.99 (s, 3H), 2.24 (s, 3H), 1.65 - 1.52 (m, 1H), 0.86 (d, J = 5.60 Hz, 3H), 0.74 (d, J = 5.60 Hz, 3H)
( S )-4-(2-(4-Methylphenylsulfonamido)-3-(4-morpholinophenylamino)-3-oxopropyl)phenyl 4-methylbenzenesulfonate
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.62 (s, 1H), 9.18 (s, 1H), 8.05 (s, 1H), 7.49 (d, J = 8.00 Hz, 2H), 7.15 (d, J = 8.40 Hz, 4H), 6.93 (d, J = 8.40 Hz, 2H), 6.83 (d, J = 9.20 Hz, 2H), 6.58 (d, J = 8.00 Hz, 2H), 3.95 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.60 Hz, 4H), 2.78 - 2.58 (m, 2H), 2.25 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -imidazol-4-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) 7.80-7.71 (d, J = 9.00 Hz, 2H), 7.59 (s, 4H), 7.45 - 7.41 (d, J = 15.0 Hz 2H), 6.98 - 6.96 (d, J = 11.5 Hz, 2H), 6.75 (brs, 1H), 4.31 - 4.28 (t, J = 7.50 Hz, 1H), 3.77 (s, 3H), 2.92 - 2.90 (dd, J 1 = 14.0, 7.00 Hz, 1H), 2.77 - 2.73 (dd, J = 14.0, 7.50 Hz, 1H)
( S )- N -methoxy- N ,4-dimethyl-2-(4-methylphenylsulfonamido)pentanamide
1H-NMR (400 MHz, CDCl3) δ 7.72 (d, J = 8.00 Hz, 2H), 7.27 (d, J = 8.40 Hz, 2H), 5.40 (d, J = 10.4 Hz, 1H), 4.28 (t, J = 10.4 Hz, 1H), 3.56 (s, 3H), 2.92 (s, 3H), 2.40 (m, 3H), 1.92 - 1.89 (m, 1H), 1.45 - 1.39 (m, 3H), 1.31 - 1.24 (m, 1H), 0.91 (d, J = 6.40 Hz, 6H)
( S )-3-(1 H -indol-3-yl)- N -methoxy- N -methyl-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.00 (s, 1H), 7.54 (d, J = 8.40 Hz, 2H), 7.44 (d, J = 7.60 Hz, 1H), 7.31 (d, J = 8.00 Hz, 1H), 7.16 (t, J = 7.40 Hz, 1H), 7.11 - 7.03 (m, 4H), 5.46 (d, J = 9.60 Hz, 1H), 4.61 - 4.55 (m, 1H), 3.45 (s, 3H), 3.17 - 3.12 (m, 1H), 3.05 - 3.00 (m, 1H), 2.95 (s, 3H), 2.34 (m, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)propan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.60 (d, J = 8.40 Hz, 2H), 7.47 (d, J = 8.00 Hz, 1H), 7.29 - 7.26 (m, 1H), 7.14 - 7.02 (m, 5H), 5.86 (d, J = 9.60 Hz, 1H), 4.66 - 4.60 (m, 1H), 3.67 - 3.63 (m, 1H), 3.58 - 3.36 (m, 13H), 3.25 - 2.97 (m, 4H)
( S )-2-(4- tert -Butylphenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propan amide
1H-NMR (400 MHz, CD3OD) δ 7.94 (s, 1H), 7.58 - 7.62 (m, 2H), 7.39 (d, J = 7.83 Hz, 1H), 7.30 - 7.34 (m, 2H), 7.25 (d, J = 7.83 Hz, 1H), 6.99 - 7.04 (m, 4H), 6.90 (s, 1H), 6.77 (d, J = 9.00 Hz, 2H), 4.06 (s, 1H), 3.75 - 3.79 (m, 4H), 3.12 - 3.20 (m, 1H), 2.98 - 3.05 (m, 5H), 1.18 (s, 9H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-(2-chlorophenyl)thiazol-2-yl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.89 - 2.93 (dd, J = 14.67, 8.80 Hz, 1H), 3.10 - 3.14 (dd, J = 14.18, 6.35 Hz, 1H), 4.34 (brs, 1H), 6.91 - 6.94 (t, J = 7.33 Hz, 1H), 7.04 - 7.07 (t, J = 7.82 Hz, 1H), 7.11 (s, 1H), 7.28 - 7.30 (d, J = 8.31 Hz, 1H), 7.37 - 7.45 (m, 6H), 7.47 - 7.49 (d, J = 7.82 Hz, 1H), 7.55 - 7.57 (d, J = 7.82 Hz, 1H), 7.60 (s, 1H), 7.81 - 7.83 (m, 1H), 8.55 (brs, 1H), 10.80 (brs, 1H), 12.53 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-(2,4-dimethoxyphenyl)thiazol-2-yl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.85 - 2.90 (dd, J = 14.18, 8.80 Hz, 1H), 3.08 - 3.12 (dd, J = 14.67, 6.35 Hz, 1H), 3.80 (s, 3H), 3.90 (s, 3H), 4.32 - 4.34 (d, J = 6.35 Hz, 1H), 6.61 - 6.63 (d, J = 8.80 Hz, 1H), 6.66 (s, 1H), 6.90 - 6.93 (t, J = 7.33 Hz, 1H), 7.03 - 7.06 (t, J = 7.33 Hz, 1H), 7.08 (s, 1H), 7.26 - 7.28 (d, J = 7.82 Hz, 1H), 7.36 - 7.40 (m, 4H), 7.47 - 7.48 (m, 2H), 7.96 - 7.98 (d, J = 8.80 Hz, 1H), 8.51 - 8.52 (d, J = 6.84 Hz, 1H), 10.78 (s, 1H), 12.39 (s, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.34 (s, 1H), 10.80 (s, 1H), 8.53 (s, 1H), 7.48 - 7.45 (m, 2H), 7.40 - 7.36 (m, 4H), 7.30 - 7.27 (m, 1H), 7.23 - 7.20 (m, 1H), 7.10 - 7.02 (m, 2H), 6.95 - 6.90 (m, 1H), 4.33 (brs, 1H), 3.12 - 3.07 (m, 1H), 2.92 - 2.86 (m, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(5-methylthiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.10 (s, 1H), 10.80 (s, 1H), 8.50 - 8.45 (d, J = 8.00 Hz, 1H), 7.46 - 7.45 (d, J = 7.50 Hz, 1H), 7.41 - 7.36 (m, 4H), 7.29 - 7.27 (d, J = 8.00 Hz, 1H), 7.11 - 7.03 (m, 3H), 6.93 - 6.90 (t, J = 7.00 Hz, 1H), 4.32 - 4.27 (m, 1H), 3.08 - 3.04 (dd, J = 14.20, 6.50 Hz, 1H), 2.89 - 2.85 (dd, J = 14.20, 8.50 Hz, 1H), 2.52 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-methylthiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.2 (s, 1H), 10.8 (s, 1H), 8.53 - 8.52 (d, J = 8.50 Hz, 1H), 7.45 - 7.44 (d, J = 8.00 Hz, 1H), 7.39 (m, 4H), 7.28 - 7.27 (d, J = 8.00 Hz, 1H), 7.07 - 7.02 (m, 2H), 6.92 - 6.90 (t, J = 7.00 Hz, 1H), 6.75 (s, 1H), 4.29 - 4.25 (m, 1H), 3.09 - 3.05 (dd, J = 14.2, 6.00 Hz, 1H), 2.89 - 2.85 (dd, J = 14.7, 8.00 Hz, 1H), 2.52 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(5-methylthiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 12.01 (s, 1H), 10.79 (s, 1H), 8.25 (d, J = 8.00 Hz, 1H), 7.46 - 7.44 (m, 2H), 7.40 - 7.39 (d, J = 7.50 Hz, 1H), 7.29 - 7.27 (d, J = 8.00 Hz, 1H), 7.10 - 7.02 (m, 5H), 6.93 - 6.90 (m, 1H), 4.28 - 4.26 (m, 1H), 3.04 - 3.03 (dd, J = 14.2, 7.00 Hz, 1H), 2.86 - 2.84 (dd, J = 14.2, 7.00 Hz, 1H), 2.32 (s, 3H), 2.22 (s, 3H)
( S )- M ethyl 4-( N -(3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.74 (s, 1H), 9.77 (s, 1H), 8.44 (s, 1H), 7.74 (d, J = 8.40 Hz, 2H), 7.62 (d, J = 8.00 Hz, 2H), 7.44 (d, J = 7.20 Hz, 1H), 7.22 (t, J = 8.40 Hz, 3H), 7.08 (d, J = 2.00 Hz, 1H), 6.99 (d, J = 7.40 Hz, 1H), 6.90 (t, J = 7.20 Hz, 1H), 6.81 (d, J = 9.20 Hz, 2H), 4.13 - 4.09 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.05 - 3.00 (m, 5H), 2.89 - 2.83 (m, 1H)
(S)-Ethyl 4-( N -(3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.74 (s, 1H), 9.76 (s, 1H), 7.73 (d, J = 8.80 Hz, 2H), 7.62 (d, J = 8.40 Hz, 2H), 7.44 (d, J = 7.60 Hz, 1H), 7.23 - 7.20 (m, 3H), 7.09 (d, J = 2.40 Hz, 1H), 7.00 - 6.81 (m, 2H), 6.81 (d, J = 9.20 Hz, 2H), 4.31 (d, J = 7.10 Hz, 2H), 4.12 - 4.09 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.05 - 3.00 (m, 5H), 2.89 - 2.83 (m, 1H), 1.34 (t, J = 7.00 Hz, 3H)
( S )-3-(4-Benzoylphenyl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.75 (s, 1H), 7.68 (d, J = 7.20 Hz, 3H), 7.57 (t, J = 5.80 Hz, 4H), 7.47 (d, J = 8.00 Hz, 2H), 7.33 (d, J = 8.00 Hz, 2H), 7.20 (d, J = 8.80 Hz, 2H), 7.12 (d, J = 7.60 Hz, 2H), 6.85 (d, J = 8.80 Hz, 2H), 4.31 (d, J = 7.10 Hz, 2H), 4.12 - 4.09 (m, 1H), 3.72 (t, J = 4.40 Hz, 4H), 3.04 - 2.95 (m, 5H), 2.20 (s, 3H)
( S )-4-( N -(3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)-N-methylbenzamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.75 (s, 1H), 9.72 (s, 1H), 8.44 (d, J = 4.00 Hz, 1H), 8.22 (s, 1H), 7.75 (d, J = 8.40 Hz, 2H), 7.67 (d, J = 8.00 Hz, 2H), 7.42 (d, J = 7.60 Hz, 1H), 7.26 (d, J = 8.00 Hz, 1H), 7.18 (d, J = 9.20 Hz, 2H), 7.07 (d, J = 1.60 Hz, 1H), 7.01 (t, J = 7.60 Hz, 1H), 6.92 (t, J = 7.60 Hz, 1H), 6.79 (d, J = 8.80 Hz, 2H), 4.15 - 4.11 (m, 1H), 3.72 (t, J = 4.80 Hz, 4H), 3.08 - 2.99 (m, 5H), 2.88 - 2.82 (m, 3H), 2.78 (d, J = 4.40 Hz, 3H)
( S )-2-(4-Methylphenylsulfonamido)- N -(4-morpholinophenyl)-3-(naphthalen-2-yl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.64 (s, 1H), 8.27 (s, 1H), 7.89 - 7.84 (m, 2H), 7.75 (t, J = 4.60 Hz, 1H), 7.50 - 7.46 (m, 4H), 7.33 (d, J = 4.20 Hz, 2H), 7.17 (d, J = 8.80 Hz, 2H), 7.09 (d, J = 8.40 Hz, 2H), 7.82 (d, J = 9.20 Hz, 2H), 4.17 - 4.14 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.40 - 3.34 (m, 1H), 3.18 - 3.13 (m, 1H), 3.02 (t, J = 5.00 Hz, 4H), 2.24 (s, 3H)
( S )- tert -Butyl 3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-ylcarbamate
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.80 (s, 1H), 9.80 (s, 1H), 7.64 (d, J = 8.00 Hz, 1H), 7.45 (d, J = 9.20 Hz, 2H), 7.32 (d, J = 8.40 Hz, 1H), 7.15 (s, 1H), 7.05 (t, J = 7.40 Hz, 1H), 6.97 (t, J = 7.20 Hz, 2H), 6.90 - 6.84 (m, 3H), 4.34 - 4.33 (m, 1H), 3.73 (t, J = 4.80 Hz, 4H), 3.13 - 2.95 (m, 6H), 1.32 (s, 9H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanoic acid
1H-NMR (400 MHz, DMSO-d6) δ 10.77 (s, 1H), 8.12 (d, J = 8.00 Hz, 1H), 7.45 (d, J = 4.00 Hz, 2H), 7.25 (t, J = 12.00 Hz, 2H), 7.12 (d, J = 16.40 Hz, 2H), 6.96 - 7.01 (m, 2H), 6.88 (t, J = 11.80 Hz, 1H), 3.86 (m, 1H), 3.03 (m, 1H), 2.83 (m, 1H), 2.30 (s, 3H)
( S )- tert -Butyl 4-(4-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-methoxyphenyl)piperazine-1-carboxylate
1H-NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 8.36 (s, 1H), 8.11 (d, J = 8.80 Hz, 1H), 7.48 (d, J = 8.00 Hz, 2H), 7.33 (d, J = 8.00 Hz, 1H), 7.28 (d, J = 8.40 Hz, 1H), 7.14 (t, J = 7.60 Hz, 1H), 7.02 - 6.96 (m, 2H), 6.92 (d, J = 2.40 Hz, 1H), 6.45 (dd, J = 2.40, 9.20 Hz, 1H), 6.41 (d, J = 2.40 Hz, 1H), 5.25 (d, J = 6.40 Hz, 1H), 4.14 - 4.05 (m, 1H), 3.57 (t, J = 5.20 Hz, 4H), 3.20 (d, J = 6.80 Hz, 2H), 3.05 (t, J = 4.80 Hz, 4H), 2.28 (s, 6H), 1.48 (s, 9H)
( S )-3-(1 H -indol-3-yl)- N -(2-methoxy-4-(piperazin-1-yl)phenyl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400MHz, DMSO-d 6 ) δ 10.69 (s, 1H), 8.97 (s, 1H), 7.50 (d, J = 9.20 Hz, 1H), 7.40 (d, J = 7.60 Hz, 2H), 7.35 (d, J = 8.00 Hz, 1H), 7.26 (d, J = 7.60 Hz, 1H), 7.08 (d, J = 2.00 Hz, 1H), 7.03 - 7.00 (m, 3H), 6.90 (d, J = 7.40 Hz, 1H), 6.56 (d, J = 2.40 Hz, 1H), 6.38 (dd, J = 2.60, 8.60 Hz, 1H), 4.12 - 4.09 (m, 2H), 3.77 (s, 3H), 3.10 - 3.05 (m, 1H), 3.01 (t, J = 4.80 Hz, 4H), 2.85 - 2.79 (m, 5H), 2.24 (s, 3H)
( S )- tert -Butyl 4-(4-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)phenyl)piperazine-1-carboxylate
1H-NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 8.02 (s, 1H), 7.46 (d, J = 8.40 Hz, 2H), 7.30 (d, J = 8.80 Hz, 2H), 7.24 (d, J = 7.20 Hz, 2H), 7.16 (t, J = 7.20 Hz, 1H), 7.04 (d, J = 8.00 Hz, 2H), 6.98 (t, J = 7.40 Hz, 1H), 6.93 (d, J = 2.40 Hz, 1H), 6.82 (d, J = 9.20 Hz, 2H), 5.19 (d, J = 5.60 Hz, 1H), 4.01 - 4.00 (m, 1H), 3.56 (t, J = 5.20 Hz, 4H), 3.18 (d, J = 6.00 Hz, 2H), 3.05 (t, J = 4.80 Hz, 4H), 2.31 (s, 3H), 1.48 (s, 9H)
( S )-3-(1 H -indol-3-yl)- N -(2-methoxy-4-morpholinophenyl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 8.13 (d, J = 8.80 Hz, 1H), 8.02 (s, 1H), 7.53 (d, J = 8.00 Hz, 2H), 7.36 (d, J = 8.00 Hz, 1H), 7.32 (d, J = 8.40 Hz, 1H), 7.18 (t, J = 7.60 Hz, 1H), 7.08 (d, J = 8.40 Hz, 2H), 7.02 (t, J = 7.00 Hz, 1H), 6.96 (d, J = 2.40 Hz, 1H), 6.47 (dd, J = 2.40, 8.80 Hz, 1H), 6.41 (d, J = 2.40 Hz, 1H), 5.08 (d, J = 6.40 Hz, 1H), 4.14 - 4.05 (m, 1H), 3.86 (t, J = 4.60 Hz, 4H), 3.73 (s, 3H), 3.29 - 3.14 (m, 2H), 3.11 (t, J = 4.80 Hz, 4H), 2.32 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-(piperazin-1-yl)phenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.76 (s, 1H), 9.63 (s, 1H), 7.51(d, J = 8.40 Hz, 2H), 7.40 (d, J = 7.60 Hz, 1H), 7.28 (d, J = 8.40 Hz, 1H), 7.17 (d, J = 8.80 Hz, 2H), 7.10 - 7.01 (m, 4H), 6.92 (t, J = 7.20 Hz, 1H), 6.79 (d, J = 9.20 Hz, 2H), 4.08 - 4.05 (m, 2H), 3.05 - 3.00 (m, 1H), 2.95 (t, J = 4.80 Hz, 4H), 2.85 - 2.79 (m, 5H), 2.23 (s, 3H)
( S )-3-(1-Formyl-1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.86 (s, 1H), 9.14 (s, 1H), 8.23 (s, 1H), 8.15 (s, 1H), 7.60 - 7.43 (m, 2H), 7.37 - 7.28 (m, 6H), 6.95 (d, J = 8.00 Hz, 2H), 6.88 (d, J = 8.40 Hz, 2H), 4.13 (m, 2H), 3.73 (t, J = 4.60 Hz, 3H), 3.05 - 2.96 (m, 5H), 2.89 - 2.83 (m, 1H), 2.20 (s, 3H)
( S )-3-(1 H -indol-3-yl)- N -(3-(4-methoxyphenyl)isoxazol-5-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3) δ 9.42 (s, 1H), 8.28 (d, J = 1.60 Hz, 1H), 7.73 - 7.70 (m, 2H), 7.42 (d, J = 8.40 Hz, 2H), 7.22 (t, J = 7.60 Hz, 1H), 7.12 (t, J = 7.60 Hz, 1H), 6.97 - 6.90 (m, 6H), 6.65 (s, 1H), 5.39 (d, J = 6.00 Hz, 1H), 4.15 - 4.09 (m, 1H), 3.83 (s, 3H), 3.26 - 3.08 (m, 2H), 2.25 (s, 3H)
( S )-Benzyl 3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanoate
1H-NMR (400 MHz, CDCl3) δ 8.06 (brs, 1H), 7.57 (d, J = 8.20 Hz, 2H), 7.42 (d, J = 8.20 Hz, 1H), 7.25 - 7.33 (m, 4H), 7.08 - 7.18 (m, 3H), 6.99 - 7.07 (m, 3H), 6.84 (d, J = 2.30 Hz, 1H), 5.24 (d, J = 9.00 Hz, 1H), 4.74 - 4.83 (m, 2H), 4.29 (td, J = 5.60, 9.00 Hz, 1H), 3.17 - 3.27 (m, 2H), 2.34 (s, 3H)
( S )-Benzyl 3-(1 H -indol-3-yl)-2-(4-methylbenzamido)propanoate
1H-NMR (400 MHz, CDCl3) δ 7.95 (brs, 1H), 7.52 - 7.60 (m, 3H), 7.33 - 7.38 (m, 3H), 7.27 - 7.32 (m, 2H), 7.16 - 7.21 (m, 3H), 7.06 (t, J = 7.43 Hz, 1H), 6.75 (d, J = 2.35 Hz, 1H), 6.64 (d, J = 7.83 Hz, 1H), 5.17 - 5.23 (m, 1H), 5.14 (d, J = 7.04 Hz, 2H), 3.44 (d, J = 5.09 Hz, 2H), 2.37 (s, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)-4-methylbenzamide
1H-NMR (400 MHz, CDCl3) δ 8.10 (brs, 1H), 7.84 (d, J = 7.83 Hz, 1H), 7.64 (d, J = 8.22 Hz, 2H), 7.38 (d, J = 8.22 Hz, 1H), 7.15 - 7.24 (m, 5H), 7.14 (d, J = 2.35 Hz, 1H), 7.03 (d, J = 7.43 Hz, 1H), 6.78 - 6.82 (m, 2H), 5.06 (dt, J = 5.09, 7.83 Hz, 1H), 3.82 - 3.86 (m, 4H), 3.57 (dd, J = 5.09, 14.48, 4H)
( S )-3-Hydroxy-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 7.79 (d, J = 8.40 Hz, 2H), 7.33-7.38 (m, 4H), 6.87 (d, J = 9.20 Hz, 2H), 5.69 (s, 1H), 4.11 (d, J = 10.40 Hz, 1H), 3.85 - 3.87 (m, 5H), 3.49 - 3.50 (m, 1H), 3.36 - 3.39 (m, 1H), 3.12 (t, J = 5.00 Hz, 4H), 2.43 (s, 3H), 2.30 (s, 1H)
( S )-3-Methyl-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)butanamide
1H-NMR (400 MHz, DMSO-d6) δ 9.56 (s, 1H), 7.81 (s, 1H), 7.62 (d, J = 8.00 Hz, 2H), 7.20 (d, J = 8.40 Hz, 2H), 7.13 (d, J = 8.80 Hz, 2H), 6.81 (d, J = 8.80 Hz, 2H), 3.71 (t, J = 4.80 Hz, 4H), 3.53 (d, J = 7.60 Hz, 1H), 3.00 (t, J = 4.60 Hz, 4H), 1.81 - 1.86 (m, 1H), 0.82 (q, J = 6.10 Hz, 6H)
( S )-1-(3-(1 H -indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-3-phenylurea
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.90 (s, 1H), 8.72 (s, 1H), 7.53 (d, J = 7.60 Hz, 1H), 7.36 (t, J = 8.20 Hz, 3H), 7.22 - 7.17 (m, 3H), 7.06 (d, J = 3.40 Hz, 1H), 7.00 - 6.89 (m, 2H), 6.59 (d, J = 8.00 Hz, 1H), 4.96 (d, J = 6.00 Hz, 1H), 3.45 - 3.42 (m, 2H), 3.26 - 3.04 (m, 8H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(6-morpholinopyridin-3-yl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.78 (s, 1H), 9.71 (s, 1H), 8.12 (s, 1H), 8.00 (d, J = 2.40 Hz, 1H), 7.53 (d, J = 8.00 Hz, 2H), 7.45 (dd, J = 2.40, 9.20 Hz, 1H), 7.40 (d, J = 8.00 Hz, 1H), 7.29 (d, J = 7.60 Hz, 1H), 7.12 (d, J = 7.60 Hz, 2H), 7.08 (d, J = 2.00 Hz, 1H), 7.04 (t, J = 7.40 Hz, 1H), 6.92 (t, J = 7.40 Hz, 1H), 6.74 (d, J = 9.20 Hz, 1H), 4.06 (s, 1H), 3.68 (t, J = 4.80 Hz, 4H), 3.34 - 3.33 (m, 4H), 3.07 - 3.01 (m, 1H), 2.88 - 2.82 (m, 1H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(2-morpholinopyrimidin-5-yl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.80 (s, 1H), 9.75 (s, 1H), 8.19 (s, 1H), 8.15 (s, 2H), 7.54 (d, J = 8.40 Hz, 2H), 7.40 (d, J = 8.00 Hz, 1H), 7.30 (d, J = 8.00 Hz, 1H), 7.15 (d, J = 8.40 Hz, 1H), 7.09 (s, 1H), 7.04 (t, J = 7.40 Hz, 1H), 6.93 (t, J = 7.40 Hz, 1H), 4.04 (m, 1H), 3.62 - 3.61 (m, 8H), 3.08 - 3.02 (m, 1H), 2.91 - 2.85 (m, 1H), 2.23 (s, 3H)
( S )-2-(4-Cyanophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.72 (s, 1H), 9.85 (s, 1H), 8.57 (s, 1H), 7.57 (s, 4H), 7.48 (d, J = 7.60 Hz, 1H), 7.29 - 7.23 (m, 3H), 7.07 - 7.01 (m, 2H), 6.93 (t, J = 7.20 Hz, 1H), 6.86 (d, J = 8.80 Hz, 2H), 4.12 (s, 1H), 3.73 (s, 4H), 3.04 - 3.00 (m, 3H), 2.90 - 2.84 (m, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.76 (s, 1H), 9.92 (s, 1H), 8.87 (s, 1H), 8.81 (s, 1H), 8.0 (d, J = 8.40 Hz, 1H), 7.60 (d, J = 8.00 Hz, 1H), 7.52 (d, J = 7.60 Hz, 1H), 7.22 - 7.19 (m, 3H), 7.12 (d, J = 1.60 Hz, 1H), 7.01 (d, J = 7.40 Hz, 1H), 6.92 (d, J = 7.40 Hz, 1H), 6.82 (d, J = 9.20 Hz, 2H), 4.21 (m, 1H), 3.73 (t, J = 4.40 Hz, 4H), 3.08 - 2.90 (m, 6H)
( S )-Methyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate
1H-NMR (400 MHz, CDCl3) δ 8.16 (s, 1H), 7.74 (d, J = 8.40 Hz, 2H), 7.27 - 7.25 (m, 4H), 6.83 (d, J = 8.80 Hz, 2H), 6.21 (d, J = 7.20 Hz, 1H), 3.9 - 3.84 (m, 5H), 3.69 (s, 3H), 3.10 (t, J = 4.60 Hz, 4H), 2.58 - 2.50 (m, 1H), 2.36 (s, 3H), 2.32 - 2.25 (m, 1H), 2.05 - 1.93 (m, 2H)
( S )-3-(1 H -benzo[ d ]imidazol-1-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.97 (s, 1H), 7.68 (s, 1H), 7.57 (d, J = 7.60 Hz, 2H), 7.38 (d, J = 8.00 Hz, 1H), 7.27 (d, J = 8.00 Hz, 1H), 7.12 - 7.00 (m, 6H), 6.72 (d, J = 8.80 Hz, 2H), 4.49 (s, 2H), 4.44 - 4.43 (m, 1H), 3.80 (t, J = 4.60 Hz, 4H), 3.03 (t, J = 4.60 Hz, 4H), 2.24 (s, 3H)
( R )-3-(2,3-dioxo-3,4-dihydroquinoxalin-1(2 H )-yl)-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 7.48 (d, J = 8.80 Hz, 2H), 7.43 (d, J = 7.60 Hz, 2H), 7.37 (d, J = 8.00 Hz, 1H), 7.32 (s, 1H), 7.27 - 7.20 (m, 2H), 7.07 (d, J = 7.20 Hz, 1H), 6.91 (t, J = 6.60 Hz, 4H), 4.75 - 4.68 (m, 1H), 4.32 (d, J = 12.4 Hz, 2H), 3.87 (s, 4H), 3.14 (s, 4H), 2.26 (s, 3H)
( S )- N -(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)-5-(trifluoromethyl)picolinamide
1H-NMR (400 MHz, CDCl3) δ 8.82 (s, 1H), 8.35 (d, J = 8.00 Hz, 1H), 8.22 (s, 1H), 8.13 (d, J = 8.00 Hz, 1H), 7.71 (d, J = 8.00 Hz, 2H), 7.28 - 7.25 (m, 2H), 7.19 (d, J = 8.40 Hz, 2H), 6.81 (d, J = 8.80 Hz, 2H), 3.85 (t, J = 4.80 Hz, 4H), 3.80 - 3.76 (m, 1H), 3.45 - 3.39 (m, 2H), 3.09 (t, J = 4.60 Hz, 4H), 2.31 (s, 3H), 1.87 - 1.73 (m, 2H), 1.60 - 1.55 (m, 2H), 1.33 - 1.30 (m, 2H)
( S )-Benzyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate
1H-NMR (400 MHz, CDCl3) δ 8.25 (s, 1H), 7.71 (d, J = 8.00 Hz, 2H), 7.36 - 7.30 (m, 5H), 7.21 (d, J = 8.80 Hz, 2H), 7.16 (d, J = 8.00 Hz, 2H), 6.77 (d, J = 8.80 Hz, 2H), 6.30 (d, J = 7.60 Hz, 1H), 5.12 - 5.04 (m, 2H), 3.95 - 3.90 (m, 1H), 3.83 (t, J = 4.60 Hz, 4H), 3.06 (t, J = 4.80 Hz, 4H), 2.55 - 2.48 (m, 1H), 2.36 - 2.30 (m, 1H), 2.28 (s, 3H), 2.06 - 2.03 (m, 1H), 1.96 - 1.93 (m, 1H)
( S )-Benzyl 3-(4-methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoate
1H-NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 7.75 (d, J = 8.00 Hz, 2H), 7.33 - 7.23 (m, 9H), 6.81 (d, J = 8.80 Hz, 2H), 6.25 (d, J = 8.80 Hz, 1H), 5.09 - 5.00 (m, 2H), 4.22 - 4.21 (m, 1H), 3.84 (t, J = 4.80 Hz, 4H), 3.08 (t, J = 4.80 Hz, 4H), 3.03 (dd, J = 4.00, 17.2 Hz, 1H), 2.41 (dd, J = 6.20, 17.4 Hz, 1H), 2.36 (s, 3H)
(S)-4-Methyl-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide
1H-NMR (400 MHz, CDCl3)δ 8.73 (s, 1H), 7.69 (d, J = 8.00 Hz, 2H), 7.42 (d, J = 8.00 Hz, 2H), 7.22 (d, J = 8.80 Hz, 2H), 6.84 - 6.80 (m, 3H) 4.90 - 4.86 (m, 1H), 3.84 (t, J = 4.80 Hz, 4H), 3.08 (t, J = 4.80 Hz, 4H), 2.39 (s, 3H), 1.90 - 1.88 (m, 1H), 1.86 - 1.71 (m, 2H), 0.97 (d, J = 6.40 Hz, 3H), 0.90 (d, J = 6.40 Hz, 3H)
2-(4-Methylphenylsulfonamido)- N -(4-morpholinophenyl)acetamide
1H-NMR (400 MHz, CDCl3)δ 7.96 (s, 1H), 7.76 (d, J = 8.40 Hz, 2H), 7.35 - 7.32 (m, 4H), 6.85 (d, J = 8.80 Hz, 2H), 5.31 (t, J = 6.80 Hz, 1H), 3.85 (t, J = 4.80 Hz, 4H), 3.69 (d, J = 6.40 Hz, 2H), 3.11 (t, J = 4.80 Hz, 4H), 2.42 (s, 3H)
( S )-3-(4-Methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoic acid
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.77 (s, 1H), 7.65 - 7.20 (m, 4H), 7.21 (d, J = 4.00 Hz, 2H), 6.82 (d, J = 8.80 Hz, 2H), 4.17 (t, J = 7.00 Hz, 1H), 3.72 (t, J = 4.40 Hz, 4H), 3.02 (t, J = 4.60 Hz, 4H), 2.57 (dd, J = 16.2, 6.60 Hz, 1H), 2.35 (dd, J = 16.0, 7.60 Hz, 1H), 2.25 (s, 3H)
( S )-4-(4-Methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoic acid
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.67 (s, 1H), 7.65 (d, J = 8.40 Hz, 2H), 7.25 (d, J = 7.60 Hz, 2H), 7.19 (d, J = 8.80 Hz, 2H), 6.84 (d, J = 8.40 Hz, 2H), 3.83 - 3.79 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.80 Hz, 4H), 2.26 (s, 3H), 2.20 - 2.11 (m, 2H), 1.80 - 1.70 (m, 2H)
(S)-3-(4-hydroxyphenyl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.61 (s, 1H), 9.18 (s, 1H), 8.05 (s, 1H), 7.49 (d, J = 8.00 Hz, 2H), 7.15 (d, J = 8.40 Hz, 4H), 6.93 (d, J = 7.60 Hz, 2H), 6.82 (d, J = 9.20 Hz, 2H), 6.57 (d, J = 8.80 Hz, 2H), 3.98 - 3.85 (m, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.01 (t, J = 4.60 Hz, 4H), 2.78 - 2.73 (m, 1H), 2.67 - 2.59 (m, 1H), 2.33 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -phenylpropanamide
1H-NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 8.10 (s, 1H), 7.45 (d, J = 8.40 Hz, 2H), 7.34 (d, J = 7.60 Hz, 2H), 7.30 - 7.24 (m, 4H), 7.17 - 7.11 (m, 2H), 7.09 - 6.92 (m, 3H), 6.91 (s, 1H), 5.19 (d, J = 5.60 Hz, 1H), 4.05 - 4.01 (m, 1H), 3.20 - 3.17 (m, 2H), 2.29 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -phenylpropanamide)
1H NMR (400 MHz, DMSO-d 6) δ 10.78 (s, 1H), 9.98 (s, 1H), 8.40 (s, 1H), 7.40 - 7.39 (m, 5H), 7.36 (d, J = 8.40 Hz, 2H), 7.30 - 7.23 (m, 3H), 7.10 (s, 1H), 7.06 - 7.01 (m, 2H), 6.93 (t, J = 7.20 Hz, 1H), 4.16 - 4.13 (m, 1H), 3.05 (dd, J = 14.2, 6.00 Hz, 1H), 2.87 (dd, J = 14.7, 8.00 Hz, 1H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(thiophen-2-ylmethyl)propanamide
1H-NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 7.41 (d, J = 8.40 Hz, 2H), 7.28 - 7.24 (m, 2H), 7.16 - 7.11 (m, 2H), 7.01 - 6.88 (m, 3H), 6.87 (s, 1H), 6.81 (s, 1H), 6.74 (s, 1H), 5.13 (d, J = 6.00 Hz, 1H), 4.48 - 4.45 (m, 2H), 3.94 - 3.91 (m, 1H), 3.11 - 3.09 (m, 2H), 2.31 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(thiophen-2-ylmethyl)propanamide
1H-NMR (400 MHz, DMSO-d 6) δ 10.73 (s, 1H), 8.62 (t, J = 6.00 Hz, 1H), 8.22 (s, 1H), 7.42 - 7.33 (m, 6H), 7.27 (d, J = 8.40 Hz, 1H), 7.05 - 7.01 (m, 2H), 6.94 - 6.88 (m, 2H), 6.86 (d, J = 2.40 Hz, 1H), 4.30 - 4.26 (m, 2H), 3.99 - 3.95 (m, 1H), 2.99 (dd, J = 14.2, 6.00 Hz, 1H), 2.80 (dd, J = 14.7, 8.00 Hz, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(2-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 12.39 (s, 1H), 10.76 (s, 1H), 8.48 (s, 1H), 7.64 (s, 1H), 7.47 (d, J = 7.60 Hz, 1H), 7.41 - 7.11 (m, 6H), 7.08 - 7.01 (m, 5H), 6.91(t, J = 7.60 Hz, 1H), 4.34 - 4.30 (m, 1H), 3.91 (s, 3H), 3.12 - 3.07 (m, 1H), 2.91 - 2.85 (m, 1H)
( S )- N -(3-( N -(4-methyl-1-morpholino-1-oxopentan-2-yl)sulfamoyl)phenyl)acetamide
1H-NMR (400 MHz, CDCl3)δ 8.47 (s, 1H), 8.25 (d, J = 8.80 Hz, 1H), 7.76 (t, J = 1.80 Hz, 1H), 7.54 (d, J = 7.60 Hz, 1H), 7.45 (t, J = 8.00 Hz, 1H), 6.69 (d, J = 9.60 Hz, 1H), 4.15 - 4.08 (m, 1H), 3.59 - 3.49 (m, 2H), 3.42 - 3.18 (m, 6H), 2.16 (s, 3H), 1.99 - 1.94 (m, 1H), 1.52 - 1.45 (m, 1H), 1.18 - 1.11 (m, 1H), 0.95 (d, J = 6.80 Hz, 3H), 0.91 (d, J = 6.80 Hz, 3H)
( S )-Benzyl 4-methyl-2-(3-phenylureido)pentanoate
1H-NMR (400 MHz, CDCl3)δ 7.38 (s, 1H), 7.34 - 7.01 (m, 8H), 6.99 - 6.97 (m, 1H), 5.83 (d, J = 8.00 Hz, 1H), 5.19 - 5.07 (m, 2H), 4.65 - 4.60 (m, 1H), 1.71 - 1.57 (m, 2H), 1.51 - 1.46 (m, 1H), 0.91 (d, J = 6.40 Hz, 3H), 0.88 (d, J = 6.40 Hz, 3H)
4-Methyl- N -(2-morpholino-2-oxoethyl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3)δ 7.76 (d, J = 8.00 Hz, 2H), 7.30 (d, J = 8.00 Hz, 2H), 6.20 (t, J = 4.60 Hz, 1H), 3.79 (d, J = 4.80 Hz, 2H), 3.58 - 3.62 (m, 4H), 3.51 (t, J = 4.40 Hz, 2H), 3.32 (t, J = 4.60 Hz, 2H), 2.4 (s, 3H)
4-Methyl- N -(1-(morpholine-4-carbonyl)cyclohexyl)benzenesulfonamide
1H-NMR (400 MHz, CDCl3)δ 7.79 (d, J = 8.00 Hz, 2H), 7.29 (d, J = 8.00 Hz, 2H), 5.33 (s, 1H), 3.74 - 3.78 (m, 8H), 2.43 (s, 3H), 1.74 - 1.91 (m, 4H), 1.17 - 1.40 (m, 6H).
( S )-4-( N -(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoic acid
1H-NMR (400 MHz, CDCl3)δ 8.20 (d, J = 8.40 Hz, 2H), 7.94 (d, J = 8.40 Hz, 2H), 6.49 (d, J = 9.20 Hz, 1H), 4.46 - 4.41 (m, 1H), 3.84 - 3.78 (m, 2H), 3.65 - 3.25 (m, 14H), 1.93 - 1.89 (m, 1H), 1.56 - 1.36 (m, 2H), 0.91 (t, J = 7.00 Hz, 6H)
( S )-2-(4-Hydroxyphenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.78 (s, 1H), 10.18 (s, 1H), 9.64 (s, 1H), 7.84 (d, J = 8.40 Hz, 1H), 7.50 (d, J = 8.80 Hz, 2H), 7.39 (d, J = 7.60 Hz, 1H), 7.29 (d, J = 7.60 Hz, 1H), 7.22 (d, J = 9.20 Hz, 2H), 7.06 (d, J = 2.40 Hz, 1H), 7.03 (d, J = 7.20 Hz, 1H), 6.93 (t, J = 7.40 Hz, 1H), 6.82 (d, J = 9.20 Hz, 2H), 6.70 (d, J = 8.40 Hz, 2H), 4.08 - 4.02 (m, 1H), 3.72 (t, J = 4.80 Hz, 4H), 3.07 - 3.00 (m, 5H), 2.84 - 2.79 (m, 1H)
( S )-4-( N -(3-(1 H -indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoic acid
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.77 (s, 1H), 9.83 (s, 1H), 8.43 (d, J = 9.20 Hz, 1H), 7.76 (d, J = 8.00 Hz, 2H), 7.63 (d, J = 8.40 Hz, 2H), 7.44 (d, J = 7.60 Hz, 1H), 7.26 - 7.22 (m, 3H), 7.09 (d, J = 2.04 Hz, 1H), 7.00 (t, J = 7.20 Hz, 1H), 6.91 (t, J = 7.60 Hz, 3H), 4.14 - 4.12 (m, 1H), 3.76 (t, J = 4.60 Hz, 4H), 3.07 - 3.03 (m, 5H), 2.90 - 2.86 (m, 1H)
( S )-2-Amino-3-(1 H -indol-3-yl)- N -(4-morpholinophenyl)propanamide
1H-NMR (400 MHz, CDCl3)δ 9.27 (s, 1H), 8.21 (s, 1H), 7.70 (d, J = 8.00 Hz, 1H), 7.51 - 7.47 (m, 2H), 7.37 (d, J = 8.40 Hz, 1H), 7.22 - 7.11 (m, 2H), 7.08 (d, J = 2.40 Hz, 1H), 6.89 - 6.86 (m, 2H), 3.86 - 3.82 (m, 5H), 3.49 - 3.45 (m, 1H), 3.11 (t, J = 4.80 Hz, 4H), 3.04 - 2.99 (m, 1H), 1.81 (s, 2H)
( S )- N -(4-(4-Acetylpiperazin-1-yl)-2-methoxyphenyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3)δ 8.54 (s, 1H), 8.49 (s, 1H), 8.12 (d, J = 8.40 Hz, 1H), 7.46 (d, J = 8.40 Hz, 2H), 7.32 - 7.26 (m, 2H), 7.13 (t, J = 7.60 Hz, 1H), 7.00 - 6.95 (m, 3H), 6.92 (d, J = 2.40 Hz, 1H), 6.45 - 6.40 (m, 2H), 5.37 (d, J = 5.60 Hz, 1H), 4.09 - 4.05 (m, 1H), 3.75 (t, J = 5.40 Hz, 2H), 3.71 (s, 3H), 3.59 (t, J = 5.00 Hz, 2H), 3.21 - 3.04 (m, 6H), 2.28 (s, 3H), 2.13 (s, 3H)
( S )- N -(4-(4-Acetylpiperazin-1-yl)phenyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (400 MHz, CDCl3)δ 8.31 (s, 1H), 8.11 (s, 1H), 8.47 (d, J = 8.40 Hz, 2H), 7.31 - 7.25 (m, 5H), 7.16 (t, J = 7.60 Hz, 1H), 7.04 (d, J = 8.40 Hz, 2H), 6.99 (t, J = 7.60 Hz, 1H), 6.94 (d, J = 2.40 Hz, 1H), 6.82 (d, J = 9.20 Hz, 2H), 5.22 (d, J = 6.00 Hz, 1H), 4.02 - 4.00 (m, 1H), 3.74 (t, J = 5.00 Hz, 2H), 3.59 (t, J = 5.00 Hz, 2H), 3.18 (d, J = 6.40 Hz, 2H), 3.10 (t, J = 5.00 Hz, 2H), 3.05 (t, J = 5.00 Hz, 2H), 2.31 (s, 3H), 2.12 (s, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-(2-(4-morpholinobenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.71 (s, 1H), 10.17 (s, 2H), 7.99 (s, 1H), 7.82 (d, J = 8.80 Hz, 2H), 7.37 (d, J = 8.00 Hz, 1H), 7.33 (d, J = 8.40 Hz, 2H), 7.26 (d, J = 7.26 Hz, 1H), 7.14 (s, 1H), 7.04 - 6.98 (m, 5H), 6.90 (t, J = 7.40 Hz, 1H), 4.07 (s, 1H), 3.74 (t, J = 4.40 Hz, 4H), 3.24 (t, J = 4.80 Hz, 4H), 3.11 - 3.06 (m, 1H), 2.80 - 2.74 (m, 1H), 2.21 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-(4-morpholinophenyl)thiazol-2-yl)propanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 12.24 (s, 1H), 10.76 (s, 1H), 8.21 (s, 1H), 7.73 (d, J = 8.80 Hz, 2H), 7.46 (d, J = 8.00 Hz, 2H), 7.41 (d, J = 8.00 Hz, 1H), 7.35 (s, 1H), 7.27 (d, J = 8.40 Hz, 1H), 7.05 - 6.97 (m, 6H), 6.91 (t, J = 7.60 Hz, 1H), 4.29 (s, 1H), 3.74 (t, J = 4.60 Hz, 4H), 3.15 (t, J = 4.60 Hz, 4H), 3.10 - 3.05 (m, 1H), 2.88 - 2.82 (m, 1H), 2.18 (s, 3H)
( S )-Methyl 4-(2-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate
1H-NMR (400 MHz, DMSO-d 6 ) δ 12.39 (s, 1H), 10.77 (s, 1H), 8.25 (d, J = 8.00 Hz, 1H), 8.02 (s, 4H), 7.81 (s, 1H), 7.46 (d, J = 8.40 Hz, 2H), 7.42 (d, J = 8.00 Hz, 1H), 7.27 (d, J = 8.40 Hz, 1H), 7.06 - 7.01 (m, 4H), 6.91 (t, J = 7.60 Hz, 1H), 4.32 - 4.30 (s, 1H), 3.86 (s, 3H), 3.12 - 3.06 (m, 1H), 2.90 - 2.84 (m, 1H), 2.17 (s, 3H)
( S )-Benzyl 3-(1 H -indol-3-yl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanoate
1H-NMR (400 MHz, CDCl3)δ 8.85 (d, J = 1.60 Hz, 1H), 7.91 (s, 1H), 7.83 (dd, J = 1.60, 8.40 Hz, 1H), 7.42 (d, J = 8.40 Hz, 1H), 7.36 - 7.33 (m, 4H), 7.26 - 7.15 (m, 5H), 7.08 - 7.04 (m, 1H), 6.84 (d, J = 2.40 Hz, 1H), 5.40 (d, J = 8.80 Hz, 1H), 5.03 (s, 2H), 4.43 - 4.38 (m, 1H), 3.33 - 3.28 (m, 1H), 3.16 - 3.10 (m, 1H)
( S )-2-(4-Methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)- N 5 -(4-nitrophenyl)pentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.57 (s, 1H), 9.71 (s, 1H), 8.21 (d, J = 8.80 Hz, 2H), 8.08 (s, 1H), 7.81 (d, J = 9.20 Hz, 2H), 7.65 (d, J = 8.40 Hz, 2H), 7.22 - 7.18 (m, 4H), 6.84 (d, J = 8.80 Hz, 2H), 3.86 (t, J = 6.80 Hz, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.80 Hz, 4H), 2.46 - 2.37 (m, 2H), 2.21 (s, 3H), 1.93 - 1.79 (m, 2H)
( S )-Benzyl 5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexylcarbamate
1H-NMR (400 MHz, CD3OD)δ 7.71 (d, J = 8.00 Hz, 2H), 7.32 - 7.25 (m, 5H), 7.22 (d, J = 8.40 Hz, 2H), 7.15 (d, J = 8.40 Hz, 2H), 6.86 (d, J = 9.20 Hz, 2H), 5.06 (s, 2H), 3.82 - 3.78 (m, 5H), 3.07 - 3.03 (m, 6H), 2.26 (s, 3H), 1.69 - 1.59 (m, 2H), 1.48 - 1.28 (m, 4H)
( S )-6-Amino-2-(4-methylphenylsulfonamido)- N -(4-morpholinophenyl)hexanamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.65 (s, 1H), 7.65 (d, J = 8.40 Hz, 2H), 7.25 - 7.19 (m, 4H), 6.83 (d, J = 8.80 Hz, 2H), 3.77 - 3.71 (m, 5H), 3.02 (t, J = 4.80 Hz, 4H), 2.42 (t, J = 6.40 Hz, 2H), 2.26 (s, 3H), 1.52 - 1.44 (m, 2H), 1.24 - 1.12 (m, 4H)
( S )-3,5-Dimethoxy- N -(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)benzamide
1H-NMR (400 MHz, CDCl3)δ 8.60 (s, 1H), 7.68 (d, J = 8.00 Hz, 2H), 7.25 (d, J = 8.80 Hz, 2H), 7.14 (d, J = 8.40 Hz, 2H), 6.98 (d, J = 2.40 Hz, 2H), 6.77 (d, J = 9.20 Hz, 2H), 6.86 (t, J = 6.00 Hz, 1H), 6.58 (s, 1H), 6.35 (d, J = 7.20 Hz, 1H), 3.83 (t, J = 4.60 Hz, 4H), 3.78 - 3.75 (m, 7H), 3.39 - 3.32 (m, 2H), 3.06 (t, J = 4.80 Hz, 4H), 2.26 (s, 3H), 1.85 - 1.71 (m, 2H), 1.52 - 1.47 (m, 2H), 1.30 - 1.23 (m, 2H)
( S )- N 5 -(4-Methoxybenzyl)-2-(4-methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)pentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.60 (s, 1H), 8.25 (t, J = 5.80 Hz, 1H), 7.95 (s, 1H), 7.64 (d, J = 8.40 Hz, 2H), 7.23 (d, J = 8.40 Hz, 2H), 7.19 (d, J = 9.20 Hz, 2H), 7.14 (d, J = 8.80 Hz, 2H), 6.84 (t, J = 8.80 Hz, 4H), 4.15 (d, J = 6.00 Hz, 2H), 3.82 - 3.71 (m, 8H), 3.02 (t, J = 4.80 Hz, 4H), 2.26 (s, 3H), 2.17 - 2.05 (m, 2H), 1.82 - 1.75 (m, 2H)
( S )-2-(4-Methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)- N 5 -phenylpentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.89 (s, 1H), 9.64 (s, 1H), 7.98 (s, 1H), 7.66 (d, J = 8.00 Hz, 2H), 7.56 (d, J = 8.40 Hz, 2H), 7.28 - 7.19 (m, 6H), 7.01 (t, J = 7.40 Hz, 1H), 6.84 (d, J = 8.80 Hz, 2H), 3.86 (t, J = 6.80 Hz, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.60 Hz, 4H), 2.41 - 2.26 (m, 2H), 2.23 (s, 3H), 1.94 - 1.80 (m, 2H)
( S )-2-(4-Methylphenylsulfonamido)-5-morpholino- N -(4-morpholinophenyl)-5-oxopentanamide
1H-NMR (400 MHz, CDCl3)δ 8.75 (s, 1H), 7.74 (d, J = 8.40 Hz, 2H), 7.34 (d, J = 8.80 Hz, 2H), 7.28 (d, J = 8.00 Hz, 2H), 7.11 (d, J = 6.00 Hz, 1H), 8.65 (d, J = 8.80 Hz, 2H), 3.86 (t, J = 4.60 Hz, 1H), 3.78 - 3.65 (m, 6H), 3.59 - 3.55 (m, 1H), 3.45 - 3.33 (m, 2H), 3.10 (t, J = 5.00 Hz, 4H), 2.64 - 2.63 (m, 2H), 2.38 (s, 3H), 2.23 - 2.18 (m, 2H), 2.07 - 2.02 (m, 2H)
( S )- N 5 -(4-fluorophenyl)-2-(4-methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)pentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.99 (s, 1H), 9.68 (s, 1H), 8.04 (s, 1H), 7.65 (d, J = 8.00 Hz, 2H), 7.58 - 7.55 (m, 2H), 7.21 (t, J = 8.00 Hz, 4H), 7.12 (t, J = 8.80 Hz, 2H), 6.84 (d, J = 8.80 Hz, 2H), 3.85 (s, 1H), 3.72 (s, 4H), 3.02 (s, 4H), 2.38 - 2.26 (m, 2H), 2.22 (s, 3H), 1.89 - 1.81 (m, 2H)
( S )- N 5 -(4- tert -butylphenyl)-2-(4-methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)pentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 9.86 (s, 1H), 9.69 (s, 1H), 8.05 (s, 1H), 7.65 (d, J = 8.40 Hz, 2H), 7.47 (d, J = 8.80 Hz, 2H), 7.29 (d, J = 8.80 Hz, 2H), 7.22 - 7.19 (m, 4H), 6.84 (d, J = 8.80 Hz, 2H), 3.84 (t, J = 6.80 Hz, 1H), 3.73 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.80 Hz, 4H), 2.40 - 2.25 (m, 2H), 2.22 (s, 3H), 1.92 - 1.77 (m, 2H), 1.24 (s, 9H)
( S )-2-(4-Methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)- N 5 -(4-(trifluoromethyl)phenyl)pentanediamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.30 (s, 1H), 9.69 (s, 1H), 8.05 (s, 1H), 7.77 (d, J = 8.80 Hz, 2H), 7.65 (d, J = 8.00 Hz, 4H), 7.22 - 7.19 (m, 4H), 6.84 (d, J = 8.80 Hz, 2H), 3.86 (s, 1H), 3.72 (s, 4H), 3.02 (s, 4H), 2.44 - 2.33 (m, 2H), 2.21 (s, 3H), 1.93 - 1.82 (m, 2H)
( S )-2-(4-Methylphenylsulfonamido)- N 1 -(4-morpholinophenyl)- N 4 -(4-nitrophenyl)succinamide
1H-NMR (400 MHz, DMSO-d 6 ) δ 10.55 (s, 1H), 9.80 (s, 1H), 8.21 (d, J = 8.80 Hz, 2H), 8.18 (s, 1H), 7.75 (d, J = 9.20 Hz, 2H), 7.65 (d, J = 8.40 Hz, 2H), 7.25 (d, J = 8.80 Hz, 2H), 7.18 (d, J = 8.40 Hz, 2H), 6.84 (d, J = 8.80 Hz, 2H), 4.35 (t, J = 6.80 Hz, 1H), 3.72 (t, J = 4.60 Hz, 4H), 3.02 (t, J = 4.80 Hz, 4H), 2.78 (dd, J = 6.60, 15.40 Hz, 1H), 2.62 (dd, J = 7.80, 15.40 Hz, 1H), 2.21 (s, 3H)
( S )- N -(furan-2-ylmethyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CDCl3)δ 8.10 (s, 1H), 7.45 - 7.43 (d, J = 10.00 Hz, 2H), 7.32 (s, 1H), 7.31 - 7.30 (d, J = 5.00 Hz, 1H), 7.26 - 7.25 (d, J = 5.00 Hz, 1H), 7.18 - 7.15 (t, J = 7.50 Hz, 1H), 7.06 - 7.05 (d, J = 5.00 Hz, 2H), 7.01 - 6.98 (t, J = 7.50 Hz, 1H), 6.83 (s, 1H), 6.67 (s, 1H), 6.30 (s, 1H), 6.15 (s, 1H), 4.97 - 4.96 (d, J = 0.94 Hz, 1H), 4.40 - 4.31 (m, 2H), 3.93 - 3.90 (m, 1H), 3.15 - 3.07 (m, 2H), 2.34 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)- N -(furan-2-ylmethyl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, CDCl3)δ 8.64 (s, 1H), 7.98 (s, 3H), 7.32 - 7.22 (m, 6H), 7.18 - 7.15 (t, J = 7.50 Hz, 1H), 6.88 (s, 1H), 6.29 (s, 1H), 6.15 (s, 1H), 5.69 (s, 1H), 4.33 (m, 2H), 3.95 - 3.91 (m, 1H), 3.28 - 3.24 (m, 1H), 3.05 - 3.00 (m, 1H)
( S )-3-(1 H -indol-3-yl)- N -isopropyl-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CDCl3)δ 8.27 (s, 1H), 7.47 - 7.45 (d, J = 10.00 Hz, 2H), 7.33 - 7.31 (d, J = 10.00 Hz, 2H), 7.19 - 7.16 (t, J = 7.50 Hz, 1H), 7.07 - 7.05 (d, J = 10.00 Hz, 2H), 7.02 - 6.99 (t, J = 7.50 Hz, 1H), 6.92 (s, 1H), 6.02 - 6.00 (d, J = 10.00 Hz, 1H), 5.09 - 5.07 (d, J = 10.00 Hz, 1H), 3.97 - 3.90 (m, 1H), 3.86 - 3.82 (m, 1H), 3.15 - 3.07 (m, 2H), 2.33 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -isopropylpropanamide
1H-NMR (500 MHz, MeOD)δ 10.23 (s, 1H), 7.97 - 7.95 (d, J = 5.00 Hz, 1H), 7.50 - 7.48 (d, J = 10.00 Hz, 2H), 7.42 - 7.41 (d, J = 5.00 Hz, 1H), 7.27 - 7.25 (d, J = 10.00 Hz, 1H), 7.06 - 7.02 (m, 4H), 6.94 - 6.90 (m, 2H), 6.86 - 6.84 (d, J = 10.00 Hz, 1H), 6.80 - 6.76 (t, J = 10.00 Hz, 1H), 4.66 (s, 1H), 4.15 - 4.12 (t, J = 7.50 Hz, 1H), 3.22 - 3.18 (m, 1H), 3.03 - 2.99 (m, 1H), 2.11 (s, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 7.86 - 7.64 (d, J = 8.50 Hz, 2H), 7.31 - 7.26 (m, 4H), 7.11 - 7.08 (t, J = 7.50 Hz, 1H), 7.04 (s, 1H), 6.95 - 6.91 (m, 3H), 6.89 - 6.87 (d, J = 8.00 Hz, 2H), 4.10 - 4.07 (m, 1H), 3.85 (s, 3H), 3.35 - 3.31 (m, 1H), 3.04 - 3.00 (m, 1H), 2.26 (s, 3H)
( S )-2-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanoyl)- N -(4-methoxyphenyl)hydrazinecarboxamide
1H-NMR (500 MHz, MeOD)δ 7.39 - 7.36 (t, J = 7.00 Hz, 4H), 7.28 - 7.26 (d, J = 8.00 Hz, 1H), 7.22 - 7.20 (d, J = 7.50 Hz, 1H), 7.08 - 7.05 (t, J = 7.50 Hz, 1H), 7.01 (s, 1H), 6.98 (s, 1H), 6.97 (s, 1H), 6.89 - 6.84 (m, 3H), 3.89 - 3.86 (m, 1H), 3.76 (s, 3H), 3.25 - 3.21 (m, 1H), 2.93 - 2.89 (m, 1H), 2.30 (s, 3H)
( S )-4-Bromo- N -(1-(3,5-dimethyl-1 H -pyrazol-1-yl)-3-(1 H -indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide
1H-NMR (500 MHz, DMSO-d 6 )δ 10.76 (s, 1H), 8.65 (s, 1H), 7.66 - 7.65 (d, J = 9.50 Hz, 1H), 7.30 - 7.27 (t, J = 7.50 Hz, 3H), 7.16 - 7.15 (d, J = 8.00 Hz, 2H), 7.10 (s, 1H), 7.07 - 7.04 (t, J = 7.50 Hz, 1H), 6.96 - 6.93 (t, J = 7.50 Hz, 1H), 6.24 (s, 2H), 5.39 - 5.37 (d, J = 8.50 Hz, 1H), 3.20 - 3.16 (d, J = 14.00, 3.00 Hz, 1H), 2.89 - 2.84 (d, J = 14.00, 10.50 Hz, 1H), 2.92 (s, 3H), 2.27 (s, 3H)
( S )- N -(3-(1 H -indol-3-yl)-1-oxo-1-(3-phenyl-1 H -pyrazol-1-yl)propan-2-yl)-4-bromobenzenesulfonamide
1H-NMR (500 MHz, DMSO-d6)δ 10.77 (s, 1H), 8.86 (s, 1H), 8.48 (s, 1H), 8.00 - 7.98 (d, J = 7.50 Hz, 2H), 7.69 - 7.68 (d, J = 7.50 Hz, 1H), 7.58 - 7.55 (t, J = 7.00 Hz, 2H), 7.52 - 7.49 (t, J = 7.50 Hz, 1H), 7.29 - 7.23 (m, 4H), 7.17 (s, 1H), 7.15 (s, 1H), 7.11 - 7.04 (m, 2H), 6.98 - 6.92 (m, 1H), 5.50 - 5.49 (d, J = 7.00 Hz, 1H), 3.28 - 3.25 (d, J = 14.00, 4.00 Hz, 1H), 2.97 - 2.92 (d, J = 14.00, 10.00 Hz, 1H)
N -(( S )-1-(2-((3 S ,5 S ,7 S )-adamantane-1-carbonyl)hydrazinyl)-3-(1 H -indol-3-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (500 MHz, MeOD)δ 7.33 - 7.32 (d, J = 8.00 Hz, 1H), 7.25 - 7.20 (t, J = 7.50 Hz, 3H), 7.06 - 7.03 (t, J = 7.50 Hz, 1H), 7.00 (s, 1H), 6.91 - 6.88 (t, J = 8.00 Hz, 1H), 6.85 - 6.83 (d, J = 8.00 Hz, 2H), 4.04 - 4.01 (d, J = 9.50, 4.50 Hz, 1H), 3.29 - 3.25 (d, J = 15.00, 5.00 Hz, 1H), 2.94 - 2.89 (d, J = 15.00, 10.00 Hz, 1H), 2.24 (s, 3H), 2.02 - 2.01 (d, J = 6.00 Hz, 3H), 1.95 (s, 6H), 1.80 - 1.74 (t, J = 12.50 Hz, 6H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(p-tolyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 )δ 12.47 (s, 1H), 10.79 (s, 1H), 8.53 - 8.52 (d, J = 7.50 Hz, 1H), 7.78 - 7.77 (d, J = 8.00 Hz, 2H), 7.55 (s, 1H), 7.48 - 7.47 (d, J = 7.50 Hz, 1H), 7.44 - 7.37 (m, 4H), 7.29 - 7.27 (d, J = 8.00 Hz, 1H), 7.25 - 7.23 (d, J = 8.50 Hz, 2H), 7.09 (d, J = 2.50 Hz, 1H), 7.06 - 7.03 (t, J = 7.50 Hz, 1H), 6.94 - 6.91 (t, J = 7.50 Hz, 1H), 4.35 - 4.31 (m, 1H), 3.12 - 3.08 (d, J = 14.50, 6.50 Hz, 1H), 2.91 - 2.86 (d, J = 15.00, 10.00 Hz, 1H), 2.33 (s, 3H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -phenethylpropanamide
1H-NMR (500 MHz, CDCl3)δ 8.27 (s, 1H), 8.02 (s, 1H), 7.47 - 7.46 (d, J = 10.00 Hz, 2H), 7.32 - 7.31 (d, J = 5.00 Hz, 2H), 7.28 - 7.25 (d, J = 7.50 Hz, 2H), 7.23 - 7.22 (d, J = 5.00 Hz, 1H), 7.20 - 7.17 (t, J = 7.50 Hz, 1H), 7.08 - 7.01 (m, 5H), 6.84 (s, 1H), 6.37 - 6.35 (t, J = 5.00 Hz, 1H), 5.08 - 5.07 (d, J = 5.00 Hz, 1H), 3.43 - 3.35 (m, 2H), 3.10 - 3.07 (t, J = 7.50 Hz, 2H), 2.70 - 2.59 (m, 2H), 2.35 (s, 3H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-(4-fluorophenyl)thiazol-2-yl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, MeOD)δ 7.91 - 7.88 (m, 2H), 7.45 - 7.42 (m, 3H), 7.32 (s, 1H), 7.30 - 7.27 (m, 3H), 7.14 - 7.10 (t, J = 10.00 Hz, 2H), 7.09 - 7.06 (t, J = 7.50 Hz, 1H), 7.02 (s,1H), 6.97 - 6.94 (t, J = 7.50 Hz, 1H), 4.31 - 4.28 (m, 1H), 3.28 - 3.24 (m, 1H), 3.08 - 3.03 (m, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-nitrophenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, MeOD)δ 8.28 - 8.26 (d, J = 10.00 Hz, 2H), 8.12 - 8.10 (d, J = 10.00 Hz, 2H), 7.68 (s, 1H), 7.47 - 7.44 (m, 3H), 7.31 - 7.27 (m, 3H), 7.09 - 7.06 (t, J = 7.50 Hz, 1H), 6.97 - 6.94 (t, J = 7.50 Hz, 1H), 4.31 - 4.28 (m, 1H), 3.29 - 3.25 (m, 1H), 3.10 - 3.05 (m, 1H)
( S )- N -(3-(1 H -indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (500 MHz, MeOD)δ 7.89 - 7.88 (d, J = 8.50 Hz, 2H), 7.43 - 7.41 (d, J = 8.80 Hz, 1H), 7.28 - 7.26 (d, J = 8.00 Hz, 1H), 7.22 - 7.21 (d, J = 8.50 Hz, 2H), 7.16 - 7.14 (d, J = 8.00 Hz, 2H), 7.10 - 7.07 (t, J = 7.00 Hz, 1H), 7.03 - 7.01 (d, J = 11.00 Hz, 3H), 6.96 - 6.93 (t, J = 7.00 Hz, 1H), 4.18 - 4.15 (d, J = 10.00, 5.00 Hz, 1H), 3.87 (s, 3H), 3.35 - 3.32 (m, 1H), 3.00 - 2.95 (d, J = 10.50, 4.00 Hz, 1H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-(4-cyanophenyl)thiazol-2-yl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.88 - 2.93 (dd, J = 14.18, 8.80 Hz, 1H), 3.09 - 3.13 (dd, J = 14.18, 6.35 Hz, 1H), 4.34 - 4.35 (d, J = 6.35 Hz, 1H), 6.91 - 6.94 (t, J = 7.33 Hz, 1H), 7.02 - 7.05 (t, J = 7.82 Hz, 1H), 7.09 - 7.10 (d, J = 1.95 Hz, 1H), 7.27 - 7.28 (d, J = 8.31 Hz, 1H), 7.37 - 7.42 (m, 4H), 7.47 - 7.48 (d, J = 7.82 Hz, 1H), 7.88 - 7.91 (m, 3H), 8.05 - 8.06 (d, J = 8.31 Hz, 2H), 8.55 - 8.57 (d, J = 7.33 Hz, 1H), 10.80 (s, 1H), 12.55 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.88 - 2.92 (dd, J = 14.18, 8.80 Hz, 1H), 3.09 - 3.13 (dd, J = 14.18, 6.35 Hz, 1H), 4.33 - 4.35 (m, 1H), 6.90 - 6.93 (t, J = 7.33 Hz, 1H), 7.02 - 7.05 (t, J = 7.33 Hz, 1H), 7.09 (d, J = 1.95 Hz, 1H), 7.27 - 7.28 (d, J = 8.31 Hz, 1H), 7.37 - 7.42 (q, J = 8.31, 8.80, 7.82 Hz, 4H), 7.47 - 7.48 (d, J = 7.82 Hz, 1H), 7.78 - 7.80 (d, J = 8.31 Hz, 2H), 7.85 (s, 1H), 8.08 - 8.10 (d, J = 8.31 Hz, 2H), 8.52 - 8.54 (d, J = 7.33 Hz, 1H), 10.78 (s, 1H), 12.54 (brs, 1H).
( S )-4-Bromo- N -(1-(2-dodecanoylhydrazinyl)-3-(1 H -indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 0.86 - 0.89 (t, J = 6.84 Hz, 3H), 1.26 (s, 16H), 1.51 - 1.54 (t, J = 6.35 Hz, 2H), 2.30 - 2.37 (m, 2H), 3.13 - 3.17 (dd, J = 14.67, 7.82 Hz, 1H), 3.22 - 3.26 (dd, J = 14.67, 5.86 Hz, 1H), 4.36 - 4.38 (t, J = 6.84 Hz, 1H), 7.02 (s, 1H), 7.06 - 7.09 (t, J = 7.33 Hz, 1H), 7.18 - 7.21 (t, J = 7.33 Hz, 1H), 7.32 - 7.34 (d, J = 8.31 Hz, 1H), 7.38 - 7.39 (d, J = 8.31 Hz, 2H), 7.42 - 7.44 (d, J = 7.82 Hz, 1H), 7.47 - 7.48 (d, J = 8.31 Hz, 2H), 8.34 (brs, 1H)
( S )-4-Bromo- N -(1-(2-decanoylhydrazinyl)-3-(1 H -indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 0.87 - 0.89 (t, J = 6.35 Hz, 3H), 1.28 (s, 12H), 1.50 - 1.54 (m, 2H), 2.28 - 2.39 (m, 2H), 3.13 - 3.23 (dd, J = 14.67, 7.33 Hz, 1H), 3.23 - 3.27 (dd, J = 14.67, 5.38 Hz, 1H), 4.36 - 4.39 (t, J = 6.84 Hz, 1H), 7.02 (s, 1H), 7.06 - 7.09 (t, J = 7.82 Hz, 1H), 7.19 - 7.22 (t, J = 7.33 Hz, 1H), 7.33 - 7.34 (d, J = 8.31 Hz, 1H), 7.39 - 7.40 (d, J = 8.31 Hz, 2H), 7.42 - 7.44 (d, J = 7.82 Hz, 1H), 7.47 - 7.48 (d, J = 8.31 Hz, 2H), 8.33 (brs. 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -phenethylpropanamide
1H-NMR (500 MHz, CDCl3)δ 2.60 - 2.73 (m, 2H), 2.93 - 2.98 (dd, J = 14.18, 7.82 Hz, 1H), 3.17 - 3.21 (dd, J = 14.67, 5.38 Hz, 1H), 3.33 - 3.40 (dq, J = 13.69, 6.84x3 Hz, 1H), 3.43 - 3.49 (dq, J = 13.20, 6.84x2, 6.35 Hz, 1H), 3.83 - 3.87 (q, J = 6.35x2, 6.84 Hz, 1H), 5.26 - 5.27 (d, J = 6.35 Hz, 1H), 6.36 - 6.38 (t, J = 5.38 Hz, 1H), 6.82 (s, 1H), 7.00 - 7.03 (t, J = 7.33 Hz, 1H), 7.06 - 7.08 (d, J = 7.82 Hz, 2H), 7.19 - 7.31 (m, 10H), 8.16 (brs, 1H)
N -(( S )-1-(2-((3 S ,5 S ,7 S )-adamantane-1-carbonyl)hydrazinyl)-3-(1 H -indol-3-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 1.66 - 1.75 (m, 6H), 1.89 (s, 6H), 2.03 (s, 3H), 3.03 - 3.07 (dd, J = 14.67, 9.29 Hz, 1H), 3.26 - 3.30 (dd, J = 15.16, 4.89 Hz, 1H), 4.27 (brs, 1H), 6.54 (brs, 1H), 6.96 - 7.01 (m, 2H), 7.13 - 7.18 (m, 3H), 7.24 - 7.32 (m, 4H), 8.32 (brs, 1H), 8.49 (brs, 1H), 9.66 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-fluorophenethyl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, CDCl3)δ 2.59 - 2.71 (m, 2H), 2.92 - 3.00 (m, 1H), 3.18 - 3.22 (dd, J = 14.67, 5.86 Hz, 1H), 3.31 - 3.37 (m, 1H), 3.43 - 3.49 (m, 1H), 3.83 - 3.87 (m, 1H), 5.19 - 5.22 (m, 1H), 6.41 - 6.43 (m, 1H), 6.86 - 7.04 (m, 5H), 7.20 - 7.35 (m, 7H), 8.17 - 7.20 (m, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-methoxyphenethyl)propanamide
1H-NMR (500 MHz, CDCl3)δ 2.55 - 2.67 (m, 2H), 2.95 - 3.00 (m, 1H), 3.17 - 3.21 (m, 1H), 3.32 - 3.35 (m, 1H), 3.41 - 3.45 (m, 1H), 3.77 - 3.78 (d, J = 4.40 Hz, 3H), 3.86 (m, 1H), 5.21 - 5.23 (t, J = 4.40 Hz, 1H), 6.34 - 6.35 (d, J = 4.40 Hz, 1H), 6.80 - 6.82 (m, 3H), 6.98 - 7.05 (m, 3H), 7.20 - 7.33 (m, 7H), 8.17 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(3-phenylpropyl)propanamide
1H-NMR (500 MHz, CDCl3)δ 1.69 - 1.74 (m, 2H), 2.53 - 2.56 (t, 6.84 Hz, 2H), 2.95 - 2.99 (dd, J = 14.67, 6.84 Hz, 1H), 3.13 - 3.19 (m, 1H), 3.22 - 3.26 (dd, J = 13.20, 5.86 Hz, 2H), 3.83 - 3.86 (m, 1H), 5.20 - 5.21 (d, J = 3.91 Hz, 1H), 6.37 (brs, 1H), 6.90 (s, 1H), 7.00 - 7.03 (m, 1H), 7.11 - 7.12 (d, J = 7.33 Hz, 2H), 7.17 - 7.31 (m, 10H), 8.15 (brs, 1H)
( S )- N -((3 R ,5 R ,7 R )-adamantan-1-yl)-2-(4-bromophenylsulfonamido)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, CDCl3)δ 1.58 - 1.64 (m, 6H), 1.74 - 1.80 (m, 6H), 2.01 (s, 3H), 3.05 - 3.09 (dd, J = 14.67, 7.33 Hz, 1H), 3.15 - 3.20 (dd, J = 14.67, 6.84 Hz, 1H), 3.77 - 3.81 (q, J = 7.33, 6.84, 6.35 Hz, 1H), 5.35 - 5.36 (d, J = 6.35 Hz, 1H), 5.65 (s, 1H), 6.96 (d, J = 1.95 Hz, 1H), 7.04 - 7.07 (t, J = 7.82 Hz, 1H), 7.20 - 7.23 (t, J = 7.82 Hz, 1H), 7.33 - 7.39 (m, 6H), 8.21 (brs, 1H)
( S )- N -(3-(1 H -indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 1.77 - 1.80 (t, J = 8.31 Hz, 1H), 2.34 - 2.41 (m, 2H), 2.62 - 2.66 (m, 1H), 2.78 - 2.81 (m, 1H), 2.92 - 2.97 (m, 1H), 3.10 - 3.16 (m, 2H), 3.19 - 3.23 (m, 1H), 3.38 - 3.42 (m, 1H), 3.76 (s, 3H), 4.48 - 4.53 (m, 1H), 6.02 - 6.04 (d, J = 9.78 Hz, 1H), 6.68 - 6.66 (m, 2H), 6.77 - 6.80 (m, 2H), 7.04 (d, J = 2.44 Hz, 1H), 7.11 - 7.14 (t, J = 7.82 Hz, 1H), 7.17 - 7.20 (t, J = 7.33 Hz, 1H), 7.30 - 7.31 (d, J = 8.31 Hz, 1H), 7.50 - 7.54 (m, 3H), 7.62 - 7.64 (d, J = 8.31 Hz, 2H), 8.11 (brs, 1H)
( S )- N -(3-(1 H -indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide
1H-NMR (500 MHz, CDCl3)δ 1.65 - 1.69 (m, 1H), 2.21 - 2.24 (m, 1H), 2.28 - 2.37 (m, 4H), 2.53 - 2.56 (m, 1H), 2.66 - 2.69 (m, 1H), 2.81 - 2.84 (m, 1H), 3.04 - 3.15 (m, 2H), 3.21 - 3.25 (dd, J = 13.69, 4.89 Hz, 1H), 3.32 - 3.35 (m, 1H), 3.75 (s, 3H), 4.45 - 4.50 (td, J = 5.38x2, 4.40 Hz, 1H), 5.91 - 5.93 (d, J = 9.78 Hz, 1H), 6.59 - 6.61 (d, J = 9.29 Hz, 2H), 6.77 - 6.79 (d, J = 9.29 Hz, 2H), 7.05 - 7.06 (d, J = 2.44 Hz, 1H), 7.10 - 7.13 (t, J = 7.82 Hz, 1H), 7.16 - 7.19 (t, J = 7.33 Hz, 1H), 7.20 - 7.22 (d, J = 8.31 Hz, 2H), 7.29 - 7.31 (d, J = 7.82 Hz, 1H), 7.51 - 7.53 (d, J = 7.82 Hz, 1H), 7.68 - 7.70 (d, J = 8.31 Hz, 2H, 8.14 (brs, 1H)
( S )- N -((3 R ,5 R ,7 R )-adamantan-1-yl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CDCl3)δ 1.57 - 1.64 (m, 6H), 1.74 - 1.80 (m, 6H), 2.00 (brs, 3H), 2.34 (s, 3H), 3.04 - 3.08 (m, 1H), 3.12 - 3.16 (m, 1H), 3.78 - 3.82 (q, J = 6.84, 6.35x2 Hz, 1H), 5.13 - 5.14 (d, J = 6.35 Hz, 1H), 5.75 (s, 1H), 6.94 - 6.95 (d, J = 1.46 Hz, 1H), 7.01 - 7.04 (t, J = 7.33 Hz, 1H), 7.08 - 7.09 (d, J = 7.82 Hz, 2H), 7.15 - 7.19 (m, 1H), 7.32 - 7.36 (t, J = 8.80 Hz, 2H), 7.48 - 7.50 (d, J = 8.31 Hz, 2H), 8.27 (brs, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-methoxyphenethyl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CDCl3)δ 2.33 (s, 3H), 2.50 - 2.63 (m, 2H), 3.01 - 3.10 (m, 2H), 3.30 - 3.40 (m, 2H), 3.77 (s, 3H), 3.85 - 3.89 (q, J = 6.35 Hz, 1H), 5.03 - 5.04 (d, J = 5.86 Hz, 1H), 6.36 - 6.38 (t, 5.38 Hz, 1H), 6.77 - 6.81 (m, 3H), 6.93 - 6.95 (d, J = 8.80 Hz, 2H), 6.98 - 7.01 (t, J = 7.33 Hz, 1H), 7.04 - 7.06 (d, J = 7.82 Hz, 2H), 7.15 - 7.18 (t, J = 7.82 Hz, 1H), 7.26 - 7.31 (m, 2H), 7.43 - 7.45 (d, J = 8.31 Hz, 2H), 8.22 (brs, 1H)
( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(3-phenylpropyl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 1.40 - 1.46 (m, 2H), 2.23 (s, 3H), 2.34 - 2.37 (t, J = 7.33 Hz, 2H), 2.75 - 2.83 (m, 3H), 2.94 - 2.99 (dd, J = 14.18, 6.84 Hz, 1H), 3.89 - 3.92 (t, J = 6.84 Hz, 1H), 6.90 - 6.93 (t, J = 7.33 Hz, 1H), 7.01 - 7.04 (t, J = 7.33 Hz, 1H), 7.07 - 7.17 (m, 6H), 7.24 - 7.28 (m, 3H), 7.34 - 7.36 (d, J = 7.82 Hz, 1H), 7.48 - 7.49 (d, J = 7.82 Hz, 2H), 7.85 - 7.87 (t, J = 5.38 Hz, 1H), 7.93 (brs, 1H), 10.77 (s, 1H)
( S )- N -(4-fluorophenethyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CD3OD) δ 2.28 (s, 3H), 2.49 - 2.54 (m, 2H), 2.80 - 2.84 (dd, J = 14.18, 7.82 Hz, 1H), 3.07 - 3.14 (m, 2H), 3.23 - 3.27 (m, 1H), 3.86 - 3.89 (t, J = 7.82 Hz, 1H), 6.92 - 7.06 (m, 9H), 7.26 - 7.27 (d, J = 7.82 Hz, 1H), 7.31 - 7.33 (d, J = 7.82 Hz, 1H), 7.40 - 7.42 (d, J = 7.82 Hz, 2H)
( S )-3-( 1H -indol-3-yl)-2-(4-methylphenylsulfonamido)- N -(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.15 (s, 3H), 2.85 - 2.90 (dd, J = 14.67, 7.82 Hz, 1H), 3.07 - 3.11 (dd, J = 14.67, 6.84 Hz, 1H), 4.28 - 4.31 (t, J = 7.33 Hz, 1H), 6.89 - 6.92 (t, J = 7.33 Hz, 1H), 7.01 - 7.06 (m, 4H), 7.26 - 7.28 (d, J = 8.31 Hz, 1H), 7.40 - 7.42 (d, J = 7.82 Hz, 1H), 7.45 - 7.47 (d, J = 8.31 Hz, 2H), 7.78 - 7.80 (m, 3H), 8.06 - 8.08 (d, J = 8.31 Hz, 2H), 8.27 (brs, 1H), 10.78 (s, 1H), 12.39 (brs, 1H)
(S)- N -(2-(1 H -indol-3-yl)ethyl)-2-(4-bromophenylsulfonamido)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, CD3OD) δ 2.72 - 2.84 (m, 3H), 3.14 - 3.18 (dd, J = 14.67, 5.38 Hz, 1H), 3.27 - 3.30 (m, 1H), 3.38 - 3.42 (m, 1H), 3.92 - 3.95 (dd, 9.29, 5.38 Hz, 1H), 6.93 - 6.96 (m, 2H), 6.99 - 7.03 (m, 2H), 7.07 - 7.11 (m, 2H), 7.22 - 7.24 (m, 2H), 7.27 - 7.29 (m, 3H), 7.32 - 7.36 (dd, J = 7.82, 4.40 Hz, 2H), 7.52 - 7.53 (d, J = 7.82 Hz, 1H)
( S )- N -(3-(1 H -indol-3-yl)-1-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-1-oxopropan-2-yl)-4-methylbenzamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.33 (s, 3H), 3.23 - 3.34 (m, 2H), 3.78 (s, 3H), 4.95 - 4.99 (m, 1H), 6.97 - 7.00 (m, 3H), 7.04 - 7.07 (t, J = 7.82 Hz, 1H), 7.24 - 7.26 (d, J = 7.82 Hz, 2H), 7.30 - 7.32 (m, 2H), 7.45 (s, 1H), 7.73 - 7.75 (d, J = 7.82 Hz, 2H), 7.83 - 7.84 (d, J = 8.80 Hz, 3H), 8.62 - 8.63 (d, J = 7.82 Hz, 1H), 10.84 (s, 1H), 12.64 (s, 1H)
( S )-2-(4-Chlorophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.86 - 2.91 (dd, J = 14.18, 8.80 Hz, 1H), 3.08 - 3.12 (dd, J = 14.67, 6.35 Hz, 1H), 3.78 (s, 3H), 4.33 (brs, 1H), 6.90 - 6.93 (t, J = 7.33 Hz, 1H), 6.97 - 6.99 (d, J = 8.80 Hz, 2H), 7.02 - 7.05 (t, J = 7.33 Hz, 1H), 7.08 (d, J = 1.95 Hz, 1H), 7.22 - 7.24 (d, J = 8.80 Hz, 2H), 7.26 - 7.27 (d, J = 8.31 Hz, 1H), 7.43 (s, 1H), 7.46 - 7.48 (d, J = 8.80 Hz, 3H), 7.79 - 7.81 (d, J = 8.80 Hz, 2H), 8.50 (brs, 1H), 10.78 (s, 1H), 12.44 (brs, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-(trifluoromethyl)phenylsulfonamido)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.88 - 2.93 (dd, J = 14.67, 9.29 Hz, 1H), 3.09 - 3.13 (dd, J = 14.18, 5.18 Hz, 1H), 3.78 (s, 3H), 4.37 (brs, 1H), 6.88 - 6.91 (t, J = 7.33 Hz, 1H), 6.97 - 7.02 (m, 3H), 7.10 (d, J = 1.95 Hz, 1H), 7.22 - 7.24 (d, J = 8.31 Hz, 1H), 7.42 (s, 1H), 7.48 - 7.53 (m, 3H), 7.65 - 7.67 (d, J = 7.82 Hz, 2H), 7.79 - 7.80 (d, J = 8.31 Hz, 2H), 8.70 (brs, 1H), 10.77 (s, 1H), 12.46 (brs, 1H)
( S )-2-(4-Fluorophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, CD3OD) δ 2.87 - 2.92 (dd, J = 14.67, 8.80, Hz, 1H), 3.08 - 3.12 (dd, J = 14.18, 6.35 Hz, 1H), 3.76 (s, 3H), 4.28 - 4.31 (dd, J = 8.31, 6.84 Hz, 1H), 6.89 - 6.92 (m, 1H), 6.96 - 7.06 (m, 4H), 7.08 (s, 1H), 7.26 - 7.28 (m, 1H), 7.39 (s, 1H), 7.46 - 7.47 (d, J = 7.82 Hz, 1H), 7.54 - 7.58 (m, 2H), 7.78 - 7.81 (m, 2H), 10.82 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)- N -((1 r ,3 R ,5 S ,7 S )-3,5-dimethyladamantan-1-yl)-3-(1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, CDCl3)δ 0.80 (s, 6H), 1.08 (s, 2H), 1.22 - 1.43 (m, 8H), 1.59 (s, 2H), 2.07 (s, 1H), 3.03 - 3.07 (dd, J = 14.67, 7.33 Hz, 1H), 3.16 - 3.20 (dd, J = 14.67, 6.84 Hz, 1H), 3.77 - 3.80 (m, 1H), 5.36 - 5.37 (d, J = 6.35 Hz, 1H), 5.70 (s, 1H), 6.97 (s, 1H), 7.03 - 7.06 (t, J = 7.33 Hz, 1H), 7.20 - 7.23 (t, J = 7.33 Hz, 1H), 7.32 - 7.38 (m, 4H), 7.63 - 7.64 (d, J = 8.80 Hz, 1H), 7.77 - 7.79 (d, J = 8.31 Hz, 1H), 8.20 (s, 1H)
( S )-2-(4-Cyanophenylsulfonamido)-3-(1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.85 - 2.90 (dd, J = 14.67, 9.78 Hz, 1H), 3.05 - 3.09 (dd, J = 14.18, 5.38 Hz, 1H), 3.78 (s, 3H), 4.34 (brs, 1H), 6.89 - 6.92 (t, J = 7.82 Hz, 1H), 6.98 - 7.04 (m, 3H), 7.07 - 7.08 (d, J = 1.95 Hz, 1H), 7.22 - 7.23 (d, J = 8.31 Hz, 1H), 7.46 - 7.52 (m, 6H), 7.82 - 7.83 (d, J = 8.80 Hz, 2H), 8.74 (brs, 1H), 10.72 - 10.72 (d, J = 1.46 Hz, 1H), 12.58 (brs, 1H)
( S )-Benzyl 3-(1 H -indol-3-yl)-2-(4-methylbenzamido)propanoate
1H-NMR (500 MHz, CDCl3)δ 3.36 - 3.43 (m, 2H), 5.03 - 5.10 (m, 2H), 5.15 - 5.18 (dt, J = 7.82, 5.38x2 Hz, 1H), 6.69 - 6.70 (d, J = 2.44 Hz, 1H), 6.76 - 6.78 (d, J = 7.82 Hz, 1H), 7.01 - 7.04 (t, J = 7.33 Hz, 1H), 7.07 - 7.08 (d, J = 8.31 Hz, 2H), 7.10 - 7.13 (t, J = 7.33 Hz, 1H), 7.21 - 7.31 (m, 6H), 7.50 - 7.51 (d, J = 7.82 Hz, 1H), 7.53 - 7.54 (d, J = 8.31 Hz, 2H), 8.64 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(5-hydroxy-1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.79 - 2.83 (dd, J = 14.18, 8.31 Hz, 1H), 2.99 - 3.03 (dd, J = 14.18, 6.84 Hz, 1H), 3.77 (s, 3H), 4.31 - 4.34 (q, J = 8.31, 7.82, 7.33 Hz, 1H), 6.58 - 6.60 (dd, J = 8.80, 2.44 Hz, 1H), 6.86 (d, J = 1.95 Hz, 1H), 6.97 - 6.99 (m, 3H), 7.06 - 7.07 (d, J = 8.80 Hz, 1H), 7.40 - 7.46 (m, 4H), 7.77 - 7.84 (m, 2H), 8.46 - 8.48 (d, J = 8.31 Hz, 1H), 8.61 (brs, 1H), 10.47 - 10.48 (d, J = 1.95 Hz, 1H), 12.4 (s, 1H)
( S )-2-(4-Bromophenylsulfonamido)- N -(4-(4-methoxyphenyl)thiazol-2-yl)-3-(5-methyl-1 H -indol-3-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.33 (s, 3H), 2.82 - 2.86 (dd, J = 14.18, 8.31 Hz, 1H), 3.04 - 3.09 (dd, J = 14.67, 6.84 Hz, 1H), 3.77 (s, 3H), 4.29 (brs, 1H), 6.84 - 6.86 (d, J = 8.31 Hz, 1H), 6.97 - 7.02 (m, 3H), 7.14 - 7.16 (m, 2H), 7.41 - 7.45 (m, 5H), 7.79 - 7.81 (d, J = 8.31 Hz, 2H), 8.47 (brs, 1H), 10.64 (s, 1H), 12.40 (brs, 1H)
( S )-2-(4-Bromophenylsulfonamido)-3-(5-fluoro-1 H -indol-3-yl)- N -(4-(4-methoxyphenyl)thiazol-2-yl)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.97 - 3.02 (dd, J = 14.18, 8.80 Hz, 1H), 3.17 - 3.22 (dd, J = 14.18, 5.86 Hz, 1H), 3.81 (s, 3H), 4.24 - 4.27 (dd, J = 8.80, 6.35 Hz, 1H), 4.62 (s, 1H), 6.81 - 6.85 (td, J = 9.29x2, 2.44 Hz, 1H), 6.92 - 6.94 (d, J = 8.80 Hz, 2H), 7.08 (s, 1H), 7.12 - 7.14 (dd, J = 10.27, 1.95 Hz, 1H), 7.17 (s, 1H), 7.21 - 7.22 (dd, J = 8.80, 4.40 Hz, 1H), 7.27 - 7.29 (d, J = 8.31 Hz, 2H), 7.41 - 7.43 (d, J = 8.31 Hz, 2H), 7.77 - 7.79 (d, J = 8.31 Hz, 2H)
( S )-4-(2-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)ethyl)benzoic acid
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.28 (s, 3H), 2.54 - 2.64 (m, 2H), 2.80 - 2.85 (dd, J = 14.18, 7.82 Hz, 1H), 3.09 - 3.20 (m, 2H), 3.26 - 3.30 (dd, J = 13.20, 6.35 Hz, 1H), 3.86 - 3.89 (dd, J = 7.82, 6.35 Hz, 1H), 6.90 - 6.93 (t, J = 7.82 Hz, 1H), 6.95 (s, 1H), 7.00 - 7.02 (d, J = 8.31 Hz, 2H), 7.04 - 7.07 (t, J = 6.84 Hz, 1H), 7.14 - 7.15 (d, J = 8.31 Hz, 2H), 7.26 - 7.27 (d, J = 7.82 Hz, 1H), 7.31 - 7.32 (d, J = 7.82 Hz, 1H), 7.40 - 7.41 (d, J = 8.31 Hz, 2H), 7.90 - 7.91 (d, J = 7.82 Hz, 3H), 10.22 (s, 1H)
( S )- N -(4-bromophenethyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.27 (s, 3H), 2.36 - 2.43 (m, 2H), 2.69 - 2.73 (dd, J = 14.18, 7.82 Hz, 1H), 2.88 - 2.98 (m, 2H), 3.03 - 3.08 (dt, J = 13.20, 6.84, 6.35 Hz, 1H), 3.82 - 3.85 (t, J = 6.84 Hz, 1H), 6.89 - 6.92 (t, J = 7.33 Hz, 1H), 6.97 - 6.99 (d, 8.31 Hz, 2H), 7.01 - 7.04 (t, J = 7.33 Hz, 2H), 7.12 - 7.14 (d, J = 8.31 Hz, 2H), 7.28 - 7.32 (dd, J = 11.24, 8.31 Hz, 2H), 7.37 - 7.39 (d, J = 7.33 Hz, 2H), 7.44 - 7.46 (d, J = 7.82 Hz, 2H), 7.91 - 7.93 (t, J = 5.38 Hz, 2H), 10.75 (brs, 1H)
( S )- N -(2-(1 H -indol-3-yl)ethyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500Mz, CD3OD) δ 2.24 (s, 3H), 2.64 - 2.76 (m, 2H), 2.82 - 2.86 (dd, J = 14.67, 8.31 Hz, 1H), 3.11 - 3.15 (dd, J = 14.67, 5.86 Hz, 1H), 3.20 - 3.26 (m, 1H), 3.30 - 3.36 (m, 1H), 3.89 - 3.91 (dd, J = 8.31, 6.35 Hz, 1H), 6.91 - 7.01 (m, 6H), 7.04 - 7.10 (m, 2H), 7.25 - 7.27 (d, J = 7.82 Hz, 1H), 7.32 - 7.35 (m, 2H), 7.36 - 7.38 (d, J = 8.31 Hz, 2H), 7.48 - 7.49 (d, J = 7.82 Hz, 1H)
( S )-3-(1 H -indol-3-yl)- N -(4-methylphenethyl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CD3OD) δ 2.27 - 2.27 (d, J = 4.89 Hz, 6H), 2.43 - 2.54 (m, 2H), 2.80 - 2.85 (dd, J = 14.18, 8.13 Hz, 1H), 3.07 - 3.14 (m, 2H), 3.21 - 3.26 (m, 1H), 3.86 - 3.89 (t, J = 6.84 Hz, 1H), 6.91 - 7.07 (m, 9H), 7.25 - 7.27 (d, J = 7.82 Hz, 1H), 7.32 - 7.33 (d, J = 7.82 Hz, 1H), 7.40 - 7.41 (d, J = 7.82 Hz, 2H)
Ethyl 2-(( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1 H -indol-3-yl)propanoate
1H-NMR (500 MHz, CD3OD) δ 1.07 - 1.10 (t, J = 7.33 Hz, 3H), 2.18 (s, 3H), 2.80 - 2.85 (dd, J = 14.67, 8.80 Hz, 1H), 3.06 - 3.18 (m, 3H), 3.97 - 4.05 (m, 3H), 4.53 - 4.55 (t, J = 6.84 Hz, 1H), 6.82 - 6.84 (d, J = 7.82 Hz, 2H), 6.90 - 6.94 (m, 1H), 6.96 (s, 1H), 7.00 - 7.06 (m, 3H), 7.10 - 7.13 (td, J = 7.82,7.33 Hz, 1H), 7.24 - 7.26 (d, J = 7.82 Hz, 1H), 7.29 - 7.30 (d, J = 8.31 Hz, 2H), 7.34 - 7.36 (dt, J = 8.31x2 Hz, 2H), 7.45 - 7.46 (d, J = 7.82 Hz, 1H)
( S )- N -(4-chlorophenethyl)-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, CD3OD) δ 2.29 (s, 3H), 2.46 - 2.57 (m, 2H), 2.80 - 2.84 (dd, J = 14.18, 7.82 Hz, 1H), 3.07 - 3.14 (m, 2H), 3.24 - 3.29 (m, 1H), 3.86 - 3.89 (t, J = 6.35 Hz, 1H), 6.91 - 6.96 (m, 2H), 7.02 - 7.08 (m, 5H), 7.19 - 7.21 (d, J = 8.31 Hz, 2H), 7.26 - 7.28 (d, J = 7.82 Hz, 1H), 7.31 - 7.33 (d, J = 7.82 Hz, 1H), 7.41 - 7.42 (d, J = 7.82 Hz, 2H)
2-(( S )-3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1 H -indol-3-yl)propanoic acid
1H-NMR (500 MHz, CD3OD) δ 2.18 (s, 3H), 2.57 - 2.62 (dd, J = 14.67, 10.27, Hz, 1H), 3.12 - 3.21 (dd, J = 14.67, 3.42 Hz, 1H), 3.21 - 3.25 (dd, J = 14.67, 6.35 Hz, 1H), 3.37 - 3.41 (dd, J = 14.67, 4.89 Hz, 1H), 3.87 - 3.89 (dd, J = 9.78, 3.91 Hz, 1H), 4.51 - 4.53 (t, J = 5.86 Hz, 1H), 6.72 - 6.74 (d, J = 8.31 Hz, 2H), 6.84 (s, 1H), 6.86 - 6.89 (t, J = 7.82 Hz, 1H), 6.97 - 7.00 (t, J = 7.82 Hz, 1H), 7.02 - 7.09 (m, 2H), 7.13 - 7.15 (m, 3H), 7.20 - 7.21 (d, J = 7.82 Hz, 1H), 7.29 - 7.32 (dd, J = 7.33, 6.84 Hz, 2H), 7.59 - 7.61 (d, J = 7.82 Hz, 1H)
( S )-Methyl 4-(2-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.16 (s, 3H), 2.49 - 2.50 (dd, J = 14.18, 7.82, 6.35 Hz, 1H), 3.07 - 3.11 (dd, J = 14.18, 7.33, 6.84 Hz, 1H), 3.85 (s, 3H), 4.30 (brs, 1H), 6.89 - 6.92 (t, J = 7.33 Hz, 1H), 7.01 - 7.07 (m, 4H), 7.26 - 7.28 (d, J = 7.82 Hz, 1H), 7.41 - 7.42 (d, J = 7.82 Hz, 1H), 7.45 - 7.47 (d, J = 8.31 Hz, 2H), 7.80 (s, 1H), 8.01(s, 4H), 8.27 (brs, 1H), 10.79 (s, 1H), 12.41 (brs, 1H)
( S )-4-(2-(3-(1 H -indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoic acid
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.18 (s, 3H), 2.87 - 2.91 (dd. J = 14.18, 7.82 Hz, 1H), 3.09 - 3.13 (dd, J = 14.18, 6.84 Hz, 1H), 4.31 - 4.36 (q, J = 7.82x3 Hz, 1H), 6.91 - 6.94 (t, J = 7.33 Hz, 1H), 7.03 - 7.09 (m, 4H), 7.28 - 7.30 (d, J = 7.82 Hz, 1H), 7.43 - 7.44 (d, J = 7.82 Hz, 1H), 7.47 - 7.49 (d, J = 7.82 Hz, 2H), 7.80 (s, 1H), 7.99 - 8.03 (m, 4H), 8.28 - 8.30 (d, J = 8.80 Hz, 1H), 10.81 (s, 1H), 12.43 (s, 1H), 12.98 (brs, 1H)
( S )-3-(Benzo[ d ]oxazol-2-ylamino)- N -(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.13 (s, 3H), 3.51 - 3.55 (m, 2H), 3.79 (s, 3H), 4.35 - 4.36 (d, J = 5.38 Hz, 1H), 6.98 - 7.01 (m, 3H), 7.11 - 7.15 (m, 3H), 7.22 - 7.24 (d, J = 7.82 Hz, 1H), 7.30 - 7.32 (d, J = 7.82 Hz, 1H), 7.44 (s, 1H), 7.65 - 7.66 (d, J = 8.31 Hz, 2H), 7.80 - 7.82 (d, J = 8.31 Hz, 2H), 7.99 - 8.01 (t, J = 6.35 Hz, 1H), 8.20 - 8.21 (d, J = 5.86 Hz, 1H), 12.33 (brs, 1H)
( S )- N -(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)benzamide
1H-NMR (500 MHz, CD3OD) δ 2.20 (s, 3H), 3.63 - 3.67 (m, 1H), 3.73 - 3.75 (m, 1H), 3.88 (s, 3H), 4.33 - 4.35 (t, J = 6.35 Hz, 1H), 6.99 - 7.01 (d, J = 8.80 Hz, 2H), 7.17 - 7.18 (d, J = 7.82 Hz, 2H), 7.24 (s, 1H), 7.47 - 7.50 (m, 2H), 7.57 - 7.60 (m, 1H), 7.74 - 7.78 (dd, J = 14.18, 7.82 Hz, 4H), 7.85 - 7.86 (d, J = 8.31 Hz, 2H)
( S )- N -(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)nicotinamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.14 (s, 3H), 3.48 - 3.53 (dt, J = 13.20, 6.84, 6.35 Hz, 1H), 3.56 - 3.63 (m, 1H), 3.78 (s, 3H), 4.23 - 4.26 (t, J = 6.84 Hz, 1H), 6.97 - 6.99 (d, J = 8.80 Hz, 2H), 7.14 - 7.16 (d, J = 8.31 Hz, 2H), 7.42 (s, 1H), 7.45 - 7.48 (dd, J = 7.82, 4.89, 2.93 Hz, 1H), 7.64 - 7.66 (d, J = 8.31 Hz, 2H), 7.79 - 7.80 (d, J = 8.80 Hz, 2H), 8.01 - 8.03 (dt, J = 7.82, 1.95x2 Hz, 1H), 8.11 (brs, 1H), 8.65 - 8.68 (m, 2H), 8.84 - 8.85 (d, J = 1.46 Hz, 1H), 12.28 (brs, 1H)
( S )- N -(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)pyrimidine-5-carboxamide
1H-NMR (500 MHz, DMSO-d 6 ) δ 2.16 (s, 3H), 3.49 - 3.53 (dt, J = 13.69, 6.84 x 2 Hz, 1H), 3.57 - 3.63 (dt, J = 13.20, 6.35x2 Hz, 1H), 3.79 (s, 3H), 4.23 - 4.26 (m, 1H), 6.98 - 7.00 (d, J = 8.80 Hz, 2H), 7.17 - 7.19 (d, J = 8.31 Hz, 2H), 7.45 (s, 1H), 7.65 - 7.67 (d, J = 8.31 Hz, 2H), 7.79 - 7.81 (d, J = 8.80 Hz, 2H), 8.18 - 8.19 (d, J = 7.82 Hz, 1H), 8.87 - 8.89 (t, J = 5.86 Hz, 1H), 9.00 (s, 2H), 9.31 (s, 1H), 12.31 (brs, 1H)
실시예 2: DX2-Nanoluciferase activity (40uM) 및 Cell viability(% inhibition)
Nanoluciferase를 발현하는 plasmid에 DX2를 클로닝한 후, 해당 plasmid를 A549 세포에 transfection하였다. Transfection된 세포를 96well plate에 각 well 당 1X104개씩 seeding하였고 12시간 동안 안정화 시켰다. 화합물을 4시간 동안 처리하였고, 이후 luciferase assay를 통해 DX2의 발현 변화를 관찰할 수 있었다.
A549 세포에 화합물을 농도별로 처리한 후 72시간 후 MTT 방법으로 cell viability를 측정하였다.
이에 대한 결과는 상기 표 1에 나타내었다.
실시예 3: AIMP2-DX2 및 AIMP2 저해능 평가(nanoluciferase assay)
상기 표 1에서 우수한 효과를 나타낸 화합물들 중에서 63번 화합물을 선택하여 이하 실험을 진행하였다.
상기 63번 화합물의 IC50를 산출하기 위하여 nanoluciferase-DX2 또는 -AIMP2를 발현하는 A549 세포에 상기 63번 화합물을 농도별로 4시간 동안 처리한 후, 형광을 측정하였다.
이에 대한 결과를 도 1에 나타내었다.
도 1에 나타낸 바와 같이, 63번 화합물의 AIMP2-DX2 및 AIMP2에 대한 저해율은 AIMP2-DX2에 대해 100배 이상의 선택성을 나타내는 것으로 확인이 되었다(DX2 IC50 = 0.92 μM 및 AIMP2 IC50 >100 μM).
실시예 4: AIMP2-DX2 저해 기전 연구
종래 보고된 바에 따르면, AIMP2-DX2는 HSP70과의 결합에 의해서 안정화가 된다. 따라서, 본 발명자는 가장 우수한 AIMP2-DX2 저해능을 나타낸 상기 63번 화합물이 AIMP2-DX2와 HSP70의 결합을 저해할 수 있는지 확인해 보았다.
구체적으로, 정제된 AIMP2-DX2와 HSP70 단백질을 이용하여 상기 63번 화합물의 존재 하에 in vitro pull-down assay를 수행하였다.
이에 대한 결과를 도 2에 나타내었다.
도 2에 나타낸 바와 같이, 63번 화합물은 농도 의존적으로 AIMP2-DX2와 HSP70과의 결합을 저해하는 것으로 확인되었다.
실시예 5: In vivo 항암 효능 평가
그 다음으로, H460 세포가 이식된 마우스 모델에서 상기 63번 화합물의 항암 효능을 평가해 보았다.
구체적으로, H460 세포가 이식된 마우스에 상기 63번 화합물을 50mg/kg으로, 이틀에 한 번씩 총 15일간 복강투여하였다.
이에 대한 결과를 도 3에 나타내었다.
도 3에 나타낸 바와 같이, 63번 화합물은 종양의 성장을 현저히 억제하였으며, 투여 기간 동안 동물의 체중에는 아무런 변화가 없는 것으로 확인되었다.
실시예 6: 55번 화합물 및 89번 화합물의 in vivo 암 성장 저해효과
추가적으로, 상기 표 1에서 55번 화합물과 88번 화합물을 선택하여 in vivo 암 성장 저해효과 실험을 진행하였다.
H460 세포 (2X107)를 7주령 BALB/cAnCr 암컷 쥐의 피하 밑에 심은 후 55번 화합물 또는 89번 화합물 (50 mg/kg)와 Taxol (10 mg/kg)를 2일에 한번씩 복강으로 투여하였다. 16일간 약물을 투여하였으며, 투여시 종양의 크기와 동물의 무게를 측정하였다. 16일 후 동물을 희생시키고 제거된 종양의 크기 및 무게를 측정하였다.
이에 대한 결과를 도 4에 나타내었다.
처리된 농도에서 55번 화합물은 처리 기간동안 약 50% 정도의 암 성장 억제 효과를 보였으며, 89번 화합물은 전혀 효과를 보이지 않았다. 처리된 기간동안 동물의 몸무게 변화가 없는 것으로 보아 화합물의 부작용은 없는 것으로 판단된다.
본 발명에 따른 상기 화학식 1로 표시되는 화합물은 AIMP2-DX2의 발현을 저해하는 효과가 매우 우수하여, AIMP2-DX2에 의해 유발되는 다양한 질환들, 특히 암 치료제 개발에 매우 유용하게 활용될 수 있다.

Claims (11)

  1. 하기 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용 가능한 염:
    [화학식 1]
    Figure pat00561

    상기 화학식 1에서,
    R1은 수소; 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸; C1~C5의 카복시메틸; C7~C10의 히드록시페닐알킬; 치환 또는 비치환의 C3~C8의 사이클로알킬; 치환 또는 비치환의 C1~C5의 아미노알킬;
    Figure pat00562
    ;
    Figure pat00563
    ;
    Figure pat00564
    ;
    Figure pat00565
    ;
    Figure pat00566
    ;
    Figure pat00567
    ;
    Figure pat00568
    ;
    Figure pat00569
    ;
    Figure pat00570
    ;
    Figure pat00571
    ;
    Figure pat00572
    ;
    Figure pat00573
    ;
    Figure pat00574
    ;
    Figure pat00575
    ;
    Figure pat00576
    ;
    Figure pat00577
    ;
    Figure pat00578
    ;
    Figure pat00579
    ;
    Figure pat00580
    ;
    Figure pat00581
    ;
    Figure pat00582
    ;
    Figure pat00583
    ;
    Figure pat00584
    ;
    Figure pat00585
    ;
    Figure pat00586
    또는
    Figure pat00587
    이고,
    R2는 수소; C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐; 나프탈렌설포닐; 벤질설포닐; C1~C5의 직선형 또는 분지형 알킬 및 C1~C5의 직선형 또는 분지형 알킬아민기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤조일; 티오펜설포닐;
    Figure pat00588
    ;
    Figure pat00589
    ;
    Figure pat00590
    ; C1~C5의 알킬옥시카보닐; 또는 페닐아미노카보닐이고,
    R3은
    Figure pat00591
    ;
    Figure pat00592
    ;
    Figure pat00593
    ;
    Figure pat00594
    ;
    Figure pat00595
    ;
    Figure pat00596
    ;
    Figure pat00597
    ;
    Figure pat00598
    ;
    Figure pat00599
    ;
    Figure pat00600
    ;
    Figure pat00601
    ;
    Figure pat00602
    ;
    Figure pat00603
    ;
    Figure pat00604
    ;
    Figure pat00605
    ;
    Figure pat00606
    ;
    Figure pat00607
    ;
    Figure pat00608
    ;
    Figure pat00609
    ;
    Figure pat00610
    ;
    Figure pat00611
    ;
    Figure pat00612
    ;
    Figure pat00613
    ;
    Figure pat00614
    ;
    Figure pat00615
    ;
    Figure pat00616
    ;
    Figure pat00617
    ;
    Figure pat00618
    ;
    Figure pat00619
    ;
    Figure pat00620
    ;
    Figure pat00621
    ;
    Figure pat00622
    ;
    Figure pat00623
    ;
    Figure pat00624
    ;
    Figure pat00625
    ;
    Figure pat00626
    ;
    Figure pat00627
    ;
    Figure pat00628
    ;
    Figure pat00629
    ;
    Figure pat00630
    Figure pat00631
    ;
    Figure pat00632
    ;
    Figure pat00633
    ;
    Figure pat00634
    ;
    Figure pat00635
    ;
    Figure pat00636
    ;
    Figure pat00637
    ;
    Figure pat00638
    ;
    Figure pat00639
    ;
    Figure pat00640
    ;
    Figure pat00641
    ,
    Figure pat00642
    ;
    Figure pat00643
    ;
    Figure pat00644
    ;
    Figure pat00645
    ;
    Figure pat00646
    ;
    Figure pat00647
    ;
    Figure pat00648
    ;
    Figure pat00649
    ;
    Figure pat00650
    ;
    Figure pat00651
    ;
    Figure pat00652
    ;
    Figure pat00653
    ;
    Figure pat00654
    ;
    Figure pat00655
    ;
    Figure pat00656
    ;
    Figure pat00657
    ;
    Figure pat00658
    ;
    Figure pat00659
    ;
    Figure pat00660
    ;
    Figure pat00661
    ;
    Figure pat00662
    ;
    Figure pat00663
    ;
    Figure pat00664
    ;
    Figure pat00665
    ;
    Figure pat00666
    ;
    Figure pat00667
    ;
    Figure pat00668
    ;
    Figure pat00669
    ;
    Figure pat00670
    ;
    Figure pat00671
    ;
    Figure pat00672
    ;
    Figure pat00673
    ;
    Figure pat00674
    ;
    Figure pat00675
    또는
    Figure pat00676
    이다.
  2. 제1항에 있어서,
    상기 R1은 히드록시, 치환 또는 비치환의 페닐, 머캅토 및 C1~C5의 알킬티오로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 C1~C5의 직선형 또는 분지형 알킬; 또는 C1~C5의 알킬, 히드록시, 히드록시카보닐 및 포밀로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 인돌일메틸이고,
    상기 R2는 C1~C5의 직선형 또는 분지형 알킬, 니트로기, 아민기, 할로, -CF3, C1~C5의 알킬카보닐아미노, -COOH, C1~C5의 알콕시, 페닐, -OCH2Ph, 히드록시, -COOCH2Ph, C1~C5의 알킬옥시카보닐, -CONHCH3 및 니트릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환되거나 비치환된 벤젠설포닐이고,
    상기 R3는
    Figure pat00677
    또는
    Figure pat00678
    인 것을 특징으로 하는 화합물 또는 이의 약학적으로 허용 가능한 염.
  3. 제1항에 있어서, 상기 R1은 수소, 사이클로헥산,
    Figure pat00679
    ,
    Figure pat00680
    ,
    Figure pat00681
    ,
    Figure pat00682
    ,
    Figure pat00683
    ,
    Figure pat00684
    ,
    Figure pat00685
    ,
    Figure pat00686
    ,
    Figure pat00687
    ,
    Figure pat00688
    ,
    Figure pat00689
    ,
    Figure pat00690
    ,
    Figure pat00691
    ,
    Figure pat00692
    ,
    Figure pat00693
    ,
    Figure pat00694
    ,
    Figure pat00695
    Figure pat00696
    ,
    Figure pat00697
    ,
    Figure pat00698
    ,
    Figure pat00699
    ,
    Figure pat00700
    ,
    Figure pat00701
    ,
    Figure pat00702
    ,
    Figure pat00703
    ,
    Figure pat00704
    ,
    Figure pat00705
    ,
    Figure pat00706
    ,
    Figure pat00707
    ;
    Figure pat00708
    ;
    Figure pat00709
    ;
    Figure pat00710
    ;
    Figure pat00711
    ;
    Figure pat00712
    ;
    Figure pat00713
    ;
    Figure pat00714
    ;
    Figure pat00715
    ;
    Figure pat00716
    ;
    Figure pat00717
    ;
    Figure pat00718
    ,
    Figure pat00719
    ,
    Figure pat00720
    ,
    Figure pat00721
    ,
    Figure pat00722
    또는
    Figure pat00723
    인 것을 특징으로 하는 화합물 또는 이의 약학적으로 허용가능한 염.
  4. 제1항에 있어서, 상기 R2는 수소,
    Figure pat00724
    ,
    Figure pat00725
    ,
    Figure pat00726
    ,
    Figure pat00727
    ,
    Figure pat00728
    ,
    Figure pat00729
    ,
    Figure pat00730
    ,
    Figure pat00731
    ,
    Figure pat00732
    ,
    Figure pat00733
    ,
    Figure pat00734
    ,
    Figure pat00735
    ,
    Figure pat00736
    ,
    Figure pat00737
    ,
    Figure pat00738
    ,
    Figure pat00739
    ,
    Figure pat00740
    ,
    Figure pat00741
    ,
    Figure pat00742
    ,
    Figure pat00743
    ,
    Figure pat00744
    ,
    Figure pat00745
    ,
    Figure pat00746
    ,
    Figure pat00747
    ,
    Figure pat00748
    ,
    Figure pat00749
    ,
    Figure pat00750
    ,
    Figure pat00751
    ,
    Figure pat00752
    ,
    Figure pat00753
    ,
    Figure pat00754
    ,
    Figure pat00755
    ,
    Figure pat00756
    ,
    Figure pat00757
    ,
    Figure pat00758
    ,
    Figure pat00759
    ,
    Figure pat00760
    ,
    Figure pat00761
    ,
    Figure pat00762
    또는
    Figure pat00763
    인 것을 특징으로 하는 화합물 또는 이의 약학적으로 허용 가능한 염.
  5. 제1항에 있어서, 상기 화학식 1의 화합물은
    (S)-4-메틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
    (R)-4-메틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((R)-4-methyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
    (S)-4-메틸-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
    (R)-4-메틸-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)-펜탄-2-일)벤젠설폰아미드 ((R)-4-methyl-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)-Pentan-2-yl)benzenesulfonamide),
    (S)-N-(1-(1,1-디옥시도티오모폴리노)-4-메틸-1-옥소펜탄-2-일)-4-메틸벤젠설폰아미드((S)-N-(1-(1,1-dioxidothiomorpholino)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide),
    N-((S)-1-((R)-2-(히드록시메틸)피롤리딘-1-일)-4-메틸-1-옥소펜탄-2-일)-4-메틸벤젠설폰아미드 (N-((S)-1-((R)-2-(hydroxymethyl)pyrrolidin-1-yl)-4-methyl-1-oxopentan-2-yl)-4-methylbenzenesulfonamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(피페리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(piperidin-1-yl)phenyl)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-메틸피페리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-methylpiperidin-1-yl)phenyl) pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-(4-메틸피페리딘-1-일)피리딘-3-일)펜탄아미드 ((S)-4-Methyl-2-(4-methylphenylsulfonamido)-N-(6-(4-methylpiperidin-1-yl)pyridin-3-yl)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-(4-메틸피페리딘-1-일)피리미딘-4-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(6-(4-methylpiperidin-1-yl)pyrimidin-4-yl)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(6-모폴리노피리딘-3-일)펜탄아미드) ((S)-4-Methyl-2-(4-methylphenylsulfonamido)-N-(6-morpholinopyridin-3-yl)pentanamide),
    (S)-N-(6-((2S, 6R)-2,6-디메틸모폴리노)피리딘-3-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-N-(3-플루오로-4-모폴리노페닐)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(3-fluoro-4-morpholinophenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-N-(4-(1,1-디옥시도티오모폴리노)페닐)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드((S)-N-(4-(1,1-dioxidothiomorpholino)phenyl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-tert-부틸 4-(5-(4-메틸-2-(4-메틸페닐설폰아미도)펜타노일)피리딘-2-일)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(5-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido) pyridin-2-yl)piperazine-1-carboxylate),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(피롤리딘-1-일)페닐)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(pyrrolidin-1-yl)phenyl)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(2-모폴리노에틸)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(2-morpholinoethyl)pentanamide)
    (S)-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-니트로벤젠설폰아미드 ((S)-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-nitrobenzenesulfonamide),
    (S)-3-아미노-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤젠설폰아미드 ((S)-3-amino-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzenesulfonamide),
    (S)-2-(4-플루오로페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-fluorophenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
    (S)-2-(4-브로모페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-bromophenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(4-(트리플루오로메틸)페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfonamido) pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(3-니트로페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(3-nitrophenylsulfonamido) pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(나프탈렌-1-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(naphthalene-1-sulfonamido)pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(나프탈렌-2-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(naphthalene-2-sulfonamido)pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(phenylsulfonamido)pentanamide),
    (S)-벤질 4-메틸-2-(3-(페닐설포닐)프로판아미도)펜타노에이트((S)-Benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate),
    (S)-2-(4-메톡시페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-methoxyphenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(티오펜-2-설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(thiophene-2-sulfonamido)pentanamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(4-니트로페닐설폰아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)pentanamide),
    (S)-2-(4-이소프로필페닐설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(4-isopropylphenylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
    (S)-2-(비페닐-4-일설폰아미도)-4-메틸-N-(4-모폴리노페닐)펜탄아미드 ((S)-2-(biphenyl-4-ylsulfonamido)-4-methyl-N-(4-morpholinophenyl)pentanamide),
    (S)-4-(벤질옥시)-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-(benzyloxy)-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
    (S)-4-히드록시-N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)벤젠설폰아미드 ((S)-4-hydroxy-N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)benzenesulfonamide),
    (S)-벤질 4-(N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)펜탄-2-일)설파모일)벤조에이트 ((S)-benzyl 4-(N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoate),
    (S)-tert-부틸 3-(4-메틸페닐설폰아미도)-4-모폴리노-4-옥소부타노에이트 ((S)-tert-butyl 3-(4-methylphenylsulfonamido)-4-morpholino-4-oxobutanoate),
    (S)-4-메틸-N-(1-모폴리노-1-옥소-3-페닐프로판-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(1-morpholino-1-oxo-3-phenylpropan-2-yl)benzenesulfonamide),
    (S)-N-(3-하이드록시-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-hydroxy-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-4-메틸-N-(3-메틸-1-모폴리노-1-옥소부탄-2-일)벤젠설폰아미드 ((S)-4-methyl-N-(3-methyl-1-morpholino-1-oxobutan-2-yl)benzenesulfonamide),
    (R)-N-(3-메르캅토-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((R)-N-(3-mercapto-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (2S,3S)-3-하이드록시-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)부탄아미드 ((2S,3S)-3-hydroxy-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)butanamide),
    (2S,3S)-3-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)펜탄아미드 ((2S,3S)-3-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)pentanamide),
    (S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-2-(4-메틸페닐설폰아미도)-4-(메틸티오)-N-(4-모폴리노페닐)부탄아미드 ((S)-2-(4-methylphenylsulfonamido)-4-(methylthio)-N-(4-morpholinophenyl)butanamide),
    (S)-3-(1H-인돌-2-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-2-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) propanamide),
    (S)-3-(1-메틸-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1-methyl-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl) propanamide),
    (S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-페닐프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-phenylpropanamide),
    (S)-벤질 4-메틸-2-(4-메틸페닐설폰아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate),
    (S)-벤질 4-메틸-2-(4-메틸벤즈아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(4-methylbenzamido)pentanoate),
    (S)-벤질 2-(4-tert-부틸벤즈아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(4-tert-butylbenzamido)-4-methylpentanoate),
    (S)-벤질 2-(벤조[d][1,3]다이옥솔-5-카복스아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(benzo[d][1,3]dioxole-5-carboxamido)-4-methylpentanoate),
    (S)-벤질 2-(4-(tert-부톡시카르보닐아미노)벤즈아미도)-4-메틸펜타노에이트 ((S)-benzyl 2-(4-(tert-butoxycarbonylamino)benzamido)-4-methylpentanoate),
    (S)-벤질 4-메틸-2-(3-(페닐설포닐)프로판아미도)펜타노에이트 ((S)-benzyl 4-methyl-2-(3-(phenylsulfonyl)propanamido)pentanoate),
    (S)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드((S)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-1-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-페닐우레아 ((S)-1-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-phenylurea),
    (S)-4-tert-부틸-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)벤즈아미드 ((S)-4-tert-butyl-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)benzamide),
    (S)-N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)-3-(페닐설포닐)프로판아미드 ((S)-N-(4-methyl-1-morpholino-1-oxopentan-2-yl)-3-(phenylsulfonyl)propanamide),
    (S)-4-tert-부틸-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤즈아미드 ((S)-4-tert-butyl-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide),
    (S)-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤조[d][1,3]디옥솔-5-카복스아미드 ((S)-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzo[d][1,3]dioxole-5-carboxamide),
    (S)-4-메틸-N-(4-모폴리노페닐)-2-(3-(페닐설포닐)프로판아미도)펜탄아미드 ((S)-4-methyl-N-(4-morpholinophenyl)-2-(3-(phenylsulfonyl)propanamido)pentanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)티아졸-2-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(2-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(2-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(3-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(3-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-2-(3,5-디메틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(3,5-dimethylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4 morpholinophenyl)propanamide),
    (S)-2-(4-플루오로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-Fluorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(4-(트리플루오로메틸)페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(4-(trifluoromethyl)phenylsulfon-amido)propanamide),
    (S)-3-(5-히드록시-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(5-Hydroxy-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-모폴리노-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(5-모폴리노티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(5-morpholinothiazol-2-yl)propan amide),
    (S)-2-(2,4-디메틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(2,4-dimethylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    3-(3-에톡시-2-(4-메틸페닐설폰아미도)-3-옥소프로필)-1H-인돌-5-카르복실산 (3-(3-ethoxy-2-(4-methylphenylsulfonamido)-3-oxopropyl)-1H-indole-5-carboxylic acid),
    (S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-(1-토실-1H-이미다졸-4-일)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-(1-tosyl-1H-imidazol-4-yl)propanamide),
    (S)-N-(6-((2S,6R)-2,6-디메틸모폴린)피리딘-3-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도) ((S)-N-(6-((2S,6R)-2,6-dimethylmorpholino)pyridin-3-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (R)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((R)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-N-(3-플루오로-4-모폴리노페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(3-fluoro-4-morpholinophenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(4-니트로페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(4-nitrophenylsulfonamido)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메톡시페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methoxyphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-이소프로필페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-isopropylphenylsulfonamido)-N-(4 morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-이소프로필페닐설폰아미도)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드((S)-3-(1H-indol-3-yl)-2-(4-isopropylphenylsulfonamido)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propenamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-methylthiazol-2-yl)propanamide),
    (S)-N-(벤조[d]티아졸-2-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(benzo[d]thiazol-2-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판산 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanoic acid),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(5-모폴리노티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(5-morpholinothiazol-2-yl)pentanamide),
    (S)-N-(5-(4-메톡시페닐)-1,3,4-티아디아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-N-(5-(4-메톡시페닐)이속사졸-3-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(5-(4-methoxyphenyl)isoxazol-3-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-N-(3-(4-메톡시페닐)이속사졸-5-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(3-(4-methoxyphenyl)isoxazol-5-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메틸)페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)pentanamide),
    (S)-N-(4-(3,4-디메톡시페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(3,4-dimethoxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-N-(4-(2-브로모-4-플루오로페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(2-bromo-4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-4-(2-아미노티아졸-4-일)페닐 4-메틸-2-(4-메틸페닐설폰아미도)펜타노에이트 ((S)-4-(2-aminothiazol-4-yl)phenyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate),
    (S)-N-(4-(4-플루오로페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-fluorophenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메톡시)페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethoxy)phenyl)thiazol-2-yl)pentanamide),
    (S)-N-(4-(4-히드록시페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-hydroxyphenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide)
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-p-톨릴티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-p-tolylthiazol-2-yl)pentanamide),
    (S)-N-(4-(4-((S)-1-메톡시프로판-2-일옥시)페닐)티아졸-2-일)-4-메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-(4-(4-((S)-1-methoxypropan-2-yloxy)phenyl)thiazol-2-yl)-4-methyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-4-메틸-2-(4-메틸페닐설폰아미도)-N-(4-(4-모폴리노페닐)티아졸-2-일)펜탄아미드 ((S)-4-methyl-2-(4-methylphenylsulfonamido)-N-(4-(4-morpholinophenyl)thiazol-2-yl)pentanamide),
    (S)-메틸 4-(2-(4-메틸-2-(4-메틸페닐설폰아미도)펜타노일)티아졸-4-일)벤조에이트 ((S)-methyl 4-(2-(4-methyl-2-(4-methylphenylsulfonamido)pentanamido)thiazol-4-yl)benzoate),
    (S)-4-(2-(4-메틸페닐설폰아미도)-3-(4-모폴리노페닐아미노)-3-옥소프로필)페닐 4-메틸벤젠설포네이트 ((S)-4-(2-(4-methylphenylsulfonamido)-3-(4-morpholinophenylamino)-3-oxopropyl)phenyl 4-methylbenzenesulfonate),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-이미다졸-4-일)-N-(4-(4-메톡시페닐)티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-imidazol-4-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-N-메톡시-N, 4-디메틸-2-(4-메틸페닐설폰아미도)펜탄아미드 ((S)-N-methoxy-N,4-dimethyl-2-(4-methylphenylsulfonamido)pentanamide),
    (S)-3-(1H-인돌-3-일)-N-메톡시-N-메틸-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-methoxy-N-methyl-2-(4-methylphenylsulfonamido)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-옥소-1-(1,4,7-트리옥사-10-아자시클로도데칸-10-일)프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)propan-2-yl)-4-methylbenzenesulfonamide),
    (S)-2-(4-tert-부틸페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-tert-butylphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propan amide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-(2-클로로페닐)티아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-N-(4-(2-chlorophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-(2,4-디메톡시페닐)티아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-N-(4-(2,4-dimethoxyphenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(thiazol-2-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(5-메틸티아졸-2-일)프로판아미드 ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(5-methylthiazol-2-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-methylthiazol-2-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(5-메틸티아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(5-methylthiazol-2-yl)propanamide),
    (S)-메틸 4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조에이트 ((S)-methyl 4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate),
    (S)-에틸 4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조에이트 ((S)-ethyl 4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoate),
    (S)-3-(4-벤조일페닐)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(4-benzoylphenyl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)-N-메틸벤즈아미드 ((S)-4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)-N-methylbenzamide),
    (S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-(나프탈렌-2-일)프로판아미드 ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-(naphthalen-2-yl)propanamide),
    (S)-tert-부틸 3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일카르바메이트 ((S)-tert-butyl 3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-ylcarbamate),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판산 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoic acid),
    (S)-tert-부틸 4-(4-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-메톡시페닐)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(4-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-methoxyphenyl)piperazine-1-carboxylate),
    (S)-3-(1H-인돌-3-일)-N-(2-메톡시-4-(피페라진-1-일)페닐)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(2-methoxy-4-(piperazin-1-yl)phenyl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-tert-부틸 4-(4-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)페닐)피페라진-1-카르복실레이트 ((S)-tert-butyl 4-(4-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)phenyl)piperazine-1-carboxylate),
    (S)-3-(1H-인돌-3-일)-N-(2-메톡시-4-모폴리노페닐)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(2-methoxy-4-morpholinophenyl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(피페라진-1-일)페닐)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(piperazin-1-yl)phenyl)propanamide),
    (S)-3-(1-포밀-1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1-formyl-1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(3-(4-메톡시페닐)이속사졸-5-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(3-(4-methoxyphenyl)isoxazol-5-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로파노에이트 ((S)-benzyl 3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoate),
    (S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸벤즈아미도)프로파노에이트 ((S)-benzyl 3-(1H-indol-3-yl)-2-(4-methylbenzamido)propanoate),
    (S)-N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)-4-메틸벤즈아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)-4-methylbenzamide),
    (S)-3-하이드록시-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-hydroxy-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-3-메틸-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)부탄아미드 ((S)-3-methyl-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)butanamide),
    (S)-1-(3-(1H-인돌-3-일)-1-모폴리노-1-옥소프로판-2-일)-3-페닐우레아 ((S)-1-(3-(1H-indol-3-yl)-1-morpholino-1-oxopropan-2-yl)-3-phenylurea),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(6-모폴리노피리딘-3-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(6-morpholinopyridin-3-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(2-모폴리노피리미딘-5-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(2-morpholinopyrimidin-5-yl)propanamide),
    (S)-2-(4-시아노페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-cyanophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)-2-(6-(트리플루오로메틸)피리딘-3-설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanamide),
    (S)-메틸 4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노에이트 ((S)-methyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate),
    (S)-3-(1H-벤조[d]이미다졸-1-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((S)-3-(1H-benzo[d]imidazol-1-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (R)-3-(2,3-디옥소-3,4-디히드로퀴녹살린-1(2H)-일)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)프로판아미드 ((R)-3-(2,3-dioxo-3,4-dihydroquinoxalin-1(2H)-yl)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)propanamide),
    (S)-N-(5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실)-5-(트리플루오로메틸)피콜린아미드 ((S)-N-(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)-5-(trifluoromethyl)picolinamide),
    (S)-벤질 4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노에이트 ((S)-benzyl 4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoate),
    (S)-벤질 3-(4-메틸페닐설폰아미도)-4-(4-모폴리노페닐아미노)-4-옥소부타노에이트 ((S)-benzyl 3-(4-methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoate),
    (S)-4-메틸-N-(4-메틸-1-(4-모폴리노페닐아미노)-1-옥소펜탄-2-일)벤즈아미드
    ((S)-4-methyl-N-(4-methyl-1-(4-morpholinophenylamino)-1-oxopentan-2-yl)benzamide),
    2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)아세트아미드
    (2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)acetamide),
    (S)-3-(4-메틸페닐설폰아미도)-4-(4-모폴리노페닐아미노)-4-옥소부타노익산
    ((S)-3-(4-methylphenylsulfonamido)-4-(4-morpholinophenylamino)-4-oxobutanoic acid),
    (S)-4-(4-메틸페닐설폰아미도)-5-(4-모폴리노페닐아미노)-5-옥소펜타노익산
    ((S)-4-(4-methylphenylsulfonamido)-5-(4-morpholinophenylamino)-5-oxopentanoic acid),
    (S)-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)-3-페닐프로판아미드
    ((S)-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)-3-phenylpropanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-페닐프로판아미드
    ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-phenylpropanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-페닐프로판아미드
    ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-phenylpropanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(티오펜-2-일)메틸)프로판아미드
    ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(thiophen-2-ylmethyl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(티오펜-2-일yl)메틸)프로판아미드
    ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(thiophen-2-ylmethyl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(2-메톡시페닐)사이아졸-2-일)프로판아미드
    ((S)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(2-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-N-(3-(N-(4-메틸-1-모폴리노-1-옥소펜탄-2-일)설파모일)페닐)아세트아미드 ((S)-N-(3-(N-(4-methyl-1-morpholino-1-oxopentan-2-yl)sulfamoyl)phenyl)acetamide)) ,
    (S)-벤질 4-메틸-2-(3-페닐우레이도)펜타노에이트 ((S)-Benzyl 4-methyl-2-(3-phenylureido)pentanoate)
    4-메틸-N-(2-모폴리노-2-옥소에틸)벤젠설폰아미드 (4-Methyl-N-(2-morpholino-2-oxoethyl)benzenesulfonamide) ,
    4-메틸-N-(1-(모폴린-4-카보닐)사이클로헥실)벤젠설폰아미드 (4-Methyl-N-(1-(morpholine-4-carbonyl)cyclohexyl)benzenesulfonamide) ,
    (S)-4-(N-(4-메틸-1-옥소-1-(1,4,7-트리옥사-10-아자사이클로도데칸-10-일)펜탄-2-일)설파모일)벤조산 ((S)-4-(N-(4-methyl-1-oxo-1-(1,4,7-trioxa-10-azacyclododecan-10-yl)pentan-2-yl)sulfamoyl)benzoic acid),
    (S)-2-(4-히드록시페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-(4-Hydroxyphenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    (S)-4-(N-(3-(1H-인돌-3-일)-1-(4-모폴리노페닐아미노)-1-옥소프로판-2-일)설파모일)벤조산 ((S)-4-(N-(3-(1H-indol-3-yl)-1-(4-morpholinophenylamino)-1-oxopropan-2-yl)sulfamoyl)benzoic acid),
    (S)-2-아미노-3-(1H-인돌-3-일)-N-(4-모폴리노페닐)프로판아미드 ((S)-2-Amino-3-(1H-indol-3-yl)-N-(4-morpholinophenyl)propanamide),
    (S)-N-(4-(4-아세틸피페라진-1-일)-2-메톡시페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-(4-Acetylpiperazin-1-yl)-2-methoxyphenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-N-(4-(4-아세틸피페라진-1-일)페닐)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-(4-Acetylpiperazin-1-yl)phenyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-(2-(4-모폴리노벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-morpholinobenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(4-모폴리노페닐)싸이아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(4-morpholinophenyl)thiazol-2-yl)propanamide),
    (S)-메틸 4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조에이트 ((S)-Methyl 4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate),
    (S)-벤질 3-(1H-인돌-3-일)-2-(6-(트리플루오로메틸)피리딘-3-설폰아미도)프로파노에이트 ((S)-Benzyl 3-(1H-indol-3-yl)-2-(6-(trifluoromethyl)pyridine-3-sulfonamido)propanoate),
    (S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-(4-니트로페닐)펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-(4-nitrophenyl)pentanediamide),
    (S)-벤질 5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실카바메이트 ((S)-Benzyl 5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexylcarbamate),
    (S)-6-아미노-2-(4-메틸페닐설폰아미도)-N-(4-모폴리노페닐)헥산아미드 ((S)-6-Amino-2-(4-methylphenylsulfonamido)-N-(4-morpholinophenyl)hexanamide),
    (S)-3,5-디메톡시-N-(5-(4-메틸페닐설폰아미도)-6-(4-모폴리노페닐아미노)-6-옥소헥실)벤즈아미드 ((S)-3,5-Dimethoxy-N-(5-(4-methylphenylsulfonamido)-6-(4-morpholinophenylamino)-6-oxohexyl)benzamide),
    (S)-N 5-(4-메톡시벤질)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-Methoxybenzyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide),
    (S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-페닐펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-phenylpentanediamide),
    (S)-2-(4-메틸페닐설폰아미도)-5-모폴리노-N-(4-모폴리노페닐)-5-옥소펜탄아미드 ((S)-2-(4-Methylphenylsulfonamido)-5-morpholino-N-(4-morpholinophenyl)-5-oxopentanamide),
    (S)-N 5-(4-플루오로페닐)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-fluorophenyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide),
    (S)-N 5-(4-tert-부틸페닐)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)펜탄디아미드 ((S)-N 5-(4-tert-butylphenyl)-2-(4-methylphenylsulfonamido)-N 1-(4-morpholinophenyl)pentanediamide),
    (S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 5-(4-(트리플루오로메틸)페닐)펜탄디아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 5-(4-(trifluoromethyl)phenyl)pentanediamide),
    (S)-2-(4-메틸페닐설폰아미도)-N 1-(4-모폴리노페닐)-N 4-(4-니트로페닐)숙신아미드 ((S)-2-(4-Methylphenylsulfonamido)-N 1-(4-morpholinophenyl)-N 4-(4-nitrophenyl)succinamide),
    (S)-N-(퓨란-2-일메틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(furan-2-ylmethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(퓨란-2-일메틸)-3-(1H-인돌-3-일)프로판아미드((S)-2-(4-Bromophenylsulfonamido)-N-(furan-2-ylmethyl)-3-(1H-indol-3-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-이소프로필-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-isopropyl-2-(4-methylphenylsulfonamido)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-이소프로필프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-isopropylpropanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-(2-(4-메톡시벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로파노일)-N-(4-메톡시페닐)하이드라진카복사미드 ((S)-2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanoyl)-N-(4-methoxyphenyl)hydrazinecarboxamide),
    (S)-4-브로모-N-(1-(3,5-디메틸-1H-파이라졸-1-일)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(3,5-dimethyl-1H-pyrazol-1-yl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide),
    (S)-N-(3-(1H-인돌-3-일)-1-옥소-1-(3-페닐-1H-파이라졸-1-일)프로판-2-일)-4-브로모벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-oxo-1-(3-phenyl-1H-pyrazol-1-yl)propan-2-yl)-4-bromobenzenesulfonamide) ,
    N-((S)-1-(2-((3S,5S,7S)-아다만탄-1-카보닐)하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 (N-((S)-1-(2-((3S,5S,7S)-adamantane-1-carbonyl)hydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(p-톨릴)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(p-tolyl)thiazol-2-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-펜틸프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-phenethylpropanamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-플루오로페닐)싸이아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-fluorophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-니트로페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-nitrophenyl)thiazol-2-yl)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-(2-(4-메톡시벤조일)하이드라지닐)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(2-(4-methoxybenzoyl)hydrazinyl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-시아노페닐)싸이아졸-2-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-cyanophenyl)thiazol-2-yl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-(트리플루오로메틸)페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide),
    (S)-4-브로모-N-(1-(2-도데카노일하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(2-dodecanoylhydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide),
    (S)-4-브로모-N-(1-(2-데카노일하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)벤젠설폰아미드 ((S)-4-Bromo-N-(1-(2-decanoylhydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)benzenesulfonamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-펜틸프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-phenethylpropanamide),
    N-((S)-1-(2-((3S,5S,7S)-아다만탄-1-카보닐)하이드라지닐)-3-(1H-인돌-3-일)-1-옥소프로판-2-일)-4-브로모벤젠설폰아미드 (N-((S)-1-(2-((3S,5S,7S)-adamantane-1-carbonyl)hydrazinyl)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-플루오로펜틸)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-fluorophenethyl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-메톡시펜틸)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-methoxyphenethyl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)-N-(3-페닐프로필)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(1H-indol-3-yl)-N-(3-phenylpropyl)propanamide),
    (S)-N-((3R,5R,7R)-아다만탄-1-일)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판아미드 ((S)-N-((3R,5R,7R)-adamantan-1-yl)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-(4-(4-메톡시페닐)피페라진-1-일)-1-옥소프로판-2-일)-4-브로모벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-bromobenzenesulfonamide),
    (S)-N-(3-(1H-인돌-3-일)-1-(4-(4-메톡시페닐)피페라진-1-일)-1-옥소프로판-2-일)-4-메틸벤젠설폰아미드 ((S)-N-(3-(1H-indol-3-yl)-1-(4-(4-methoxyphenyl)piperazin-1-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide),
    (S)-N-((3R,5R,7R)-아다만탄-1-일)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-((3R,5R,7R)-adamantan-1-yl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-메톡시펜틸)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-methoxyphenethyl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(3-페닐프로필)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(3-phenylpropyl)propanamide),
    (S)-N-(4-플루오로펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-fluorophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)-N-(4-(4-(트리플루오로메틸)페닐)싸이아졸-2-일)프로판아미드 ((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)-N-(4-(4-(trifluoromethyl)phenyl)thiazol-2-yl)propanamide),
    (S)-N-(2-(1H-인돌-3-일)에틸)-2-(4-브로모페닐설폰아미도)-3-(1H-인돌-3-일)프로판아미드 ((S)-N-(2-(1H-indol-3-yl)ethyl)-2-(4-bromophenylsulfonamido)-3-(1H-indol-3-yl)propanamide),
    (S)-N-(3-(1H-인돌-3-일)-1-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-1-옥소프로판-2-일)-4-메틸벤즈아미드 ((S)-N-(3-(1H-indol-3-yl)-1-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-1-oxopropan-2-yl)-4-methylbenzamide),
    (S)-2-(4-클로로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Chlorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-2-(4-(트리플루오로메틸)페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-(trifluoromethyl)phenylsulfonamido)propanamide),
    (S)-2-(4-플루오로페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Fluorophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-((1r,3R,5S,7S)-3,5-디메틸아다만탄-1-일)-3-(1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-((1r,3R,5S,7S)-3,5-dimethyladamantan-1-yl)-3-(1H-indol-3-yl)propanamide),
    (S)-2-(4-시아노페닐설폰아미도)-3-(1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Cyanophenylsulfonamido)-3-(1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-벤질 3-(1H-인돌-3-일)-2-(4-메틸벤즈아미도)프로파노에이트 ((S)-Benzyl 3-(1H-indol-3-yl)-2-(4-methylbenzamido)propanoate),
    (S)-2-(4-브로모페닐설폰아미도)-3-(5-히드록시-1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(5-hydroxy-1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-3-(5-메틸-1H-인돌-3-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-3-(5-methyl-1H-indol-3-yl)propanamide),
    (S)-2-(4-브로모페닐설폰아미도)-3-(5-플루오로-1H-인돌-3-일)-N-(4-(4-메톡시페닐)싸이아졸-2-일)프로판아미드 ((S)-2-(4-Bromophenylsulfonamido)-3-(5-fluoro-1H-indol-3-yl)-N-(4-(4-methoxyphenyl)thiazol-2-yl)propanamide),
    (S)-4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)에틸)벤조산 ((S)-4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)ethyl)benzoic acid),
    (S)-N-(4-브로모펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-bromophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-N-(2-(1H-인돌-3-일)에틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(2-(1H-indol-3-yl)ethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-3-(1H-인돌-3-일)-N-(4-메틸펜틸)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(1H-indol-3-yl)-N-(4-methylphenethyl)-2-(4-methylphenylsulfonamido)propanamide),
    에틸 2-((S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-(1H-인돌-3-일)프로파노에이트 (Ethyl 2-((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1H-indol-3-yl)propanoate),
    (S)-N-(4-클로로펜틸)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-N-(4-chlorophenethyl)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamide),
    2-((S)-3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)-3-(1H-인돌-3-일)프로판산 (2-((S)-3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)-3-(1H-indol-3-yl)propanoic acid),
    (S)-메틸 4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조에이트 ((S)-Methyl 4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoate),
    (S)-4-(2-(3-(1H-인돌-3-일)-2-(4-메틸페닐설폰아미도)프로판아미도)싸이아졸-4-일)벤조산 ((S)-4-(2-(3-(1H-indol-3-yl)-2-(4-methylphenylsulfonamido)propanamido)thiazol-4-yl)benzoic acid),
    (S)-3-(벤조[d]옥사졸-2-일아미노)-N-(4-(4-메톡시페닐)싸이아졸-2-일)-2-(4-메틸페닐설폰아미도)프로판아미드 ((S)-3-(Benzo[d]oxazol-2-ylamino)-N-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(4-methylphenylsulfonamido)propanamide),
    (S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)벤즈아미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)benzamide),
    (S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)니코틴아미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)nicotinamide) 또는
    (S)-N-(3-((4-(4-메톡시페닐)싸이아졸-2-일)아미노)-2-(4-메틸페닐설폰아미도)-3-옥소프로필)피리미딘-5-카복사미드 ((S)-N-(3-((4-(4-methoxyphenyl)thiazol-2-yl)amino)-2-(4-methylphenylsulfonamido)-3-oxopropyl)pyrimidine-5-carboxamide)인 것을 특징으로 하는 화합물 또는 이의 약학적으로 허용 가능한 염.
  6. 제1항 내지 제5항 중 어느 한 항에 있어서, 상기 화합물은 AIMP2-DX2의 발현을 억제하는 것을 특징으로 하는 화합물 또는 이의 약학적으로 허용가능한 염.
  7. 하기 반응식에 의해 제조되는 제1항의 화합물 또는 이의 약학적으로 허용가능한 염의 제조방법:
    [반응식 1]
    Figure pat00764

    상기 반응식 1에서,
    R1, R2 및 R3는 제1항에서 정의한 바와 같다.
  8. 제1항 내지 제5항 중 어느 한 항의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 암 예방 또는 치료용 약학적 조성물.
  9. 제8항에 있어서, 상기 암은 백혈병, 뇌종양, 신장암, 위암, 피부암, 방광암, 유방암, 자궁암, 흑색종, 갑상선암, 두경부암, 림프종, 담낭암, 식도암, 폐암, 결장암, 전립선암, 난소암, 간암, 대장암, 복막암, 복막전이암 및 췌장암으로 이루어진 군에서 선택되는 것을 특징으로 하는 약학적 조성물.
  10. 제1항 내지 제5항 중 어느 한 항의 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 염증성 질환 예방 또는 치료용 약학적 조성물.
  11. 제10항에 있어서, 상기 염증성 질환은 염증성 피부질환, 크론씨 질환(Crohn's desease), 궤양성 대장염, 복막염, 골수염, 봉소염, 뇌막염, 뇌염, 췌장염, 외상 유발 쇼크, 기관지 천식, 알레르기성 비염, 낭포성 섬유증, 뇌졸중, 급성 기관지염, 만성 기관지염, 급성 세기관지염, 만성 세기관지염, 골관절염, 통풍, 척추관절병증, 강직성 척추염, 라이터 증후군, 건선성 관절병증, 장질환 척추염, 연소자성 관절병증, 연소자성 강직성 척추염, 반응성 관절병증, 감염성 관절염, 후-감염성 관절염, 임균성 관절염, 결핵성 관절염, 바이러스성 관절염, 진균성 관절염, 매독성 관절염, 라임 병, '혈관염 증후군'과 관련된 관절염, 결절성 다발동맥염, 과민성 혈관염, 루게닉 육아종증, 류마티스성 다발성근육통, 관절 세포 동맥염, 칼슘 결정 침착 관절병증, 가성 통풍, 비-관절 류마티즘, 점액낭염, 건초염, 상과염(테니스 엘보), 신경병증성 관절 질환(charco and joint), 출혈성 관절증(hemarthrosic), 헤노흐-쉔라인 자반병, 비후성 골관절병증, 다중심성 세망조직구종, 수르코일로시스(surcoilosis), 혈색소증, 겸상 적혈구증 및 기타 혈색소병증, 고지단백혈증, 저감마글로불린혈증, 가족성 지중해열, 베하트 병, 전신성 홍반성 루푸스, 재귀열, 건선, 다발성 경화증, 패혈증, 패혈성 쇼크, 다장기 기능장애 증후군, 급성 호흡곤란 증후군, 만성 폐쇄성 폐질환(chronic obstructive pulmonary disease), 류마치스성 관절염(rheumatoid arthritis), 급성 폐손상(acute lung injury) 및 기관지 폐 형성장애(broncho-pulmonary dysplasia)로 이루어진 군에서 선택되는 것을 특징으로 하는 약학적 조성물.
KR1020200038419A 2019-03-29 2020-03-30 항암활성을 갖는 신규한 화합물 및 이의 제조방법 KR102520437B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020190037271 2019-03-29
KR20190037271 2019-03-29

Publications (2)

Publication Number Publication Date
KR20200116065A true KR20200116065A (ko) 2020-10-08
KR102520437B1 KR102520437B1 (ko) 2023-04-12

Family

ID=72666766

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020200038419A KR102520437B1 (ko) 2019-03-29 2020-03-30 항암활성을 갖는 신규한 화합물 및 이의 제조방법

Country Status (6)

Country Link
US (1) US20220204497A1 (ko)
EP (1) EP3939968A4 (ko)
JP (1) JP2022528950A (ko)
KR (1) KR102520437B1 (ko)
CN (1) CN113874361A (ko)
WO (1) WO2020204548A1 (ko)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2508444B2 (ja) * 1987-06-25 1996-06-19 ソニー株式会社 カラ−陰極線管
KR20140145895A (ko) * 2013-06-14 2014-12-24 재단법인 의약바이오컨버젼스연구단 신규한 암 예방 또는 치료용 약학적 조성물

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA73543C2 (uk) * 1999-12-07 2005-08-15 Тераванс, Інк. Похідні сечовини, фармацевтична композиція та застосування похідного при приготуванні лікарського засобу для лікування захворювання, яке опосередковується мускариновим рецептором
KR100599454B1 (ko) * 2004-04-27 2006-07-12 재단법인서울대학교산학협력재단 종양 억제자로 작용하는 ａｉｍ3의 신규 용도
US7459529B2 (en) 2004-11-24 2008-12-02 Seoul National University Industry Foundation AIMP2-DX2 and its uses
KR101067816B1 (ko) 2007-11-09 2011-09-27 (주)네오믹스 Ａｉｍｐ2-ｄｘ2의 억제제를 유효성분으로 포함하는 염증성질환 예방 및 치료용 조성물
KR101632318B1 (ko) * 2009-11-05 2016-06-27 재단법인 의약바이오컨버젼스연구단 벤조헤테로사이클 유도체 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 암 예방 및 치료용 조성물
CN103403018B (zh) * 2010-12-21 2015-08-19 医药公司（莱比锡）有限公司 胰蛋白酶样丝氨酸蛋白酶抑制剂,它们的制备以及作为凝结因子IIa和Xa的选择性抑制剂的用途
JP6041303B2 (ja) * 2012-12-13 2016-12-07 Ｋｔｎバイオテック株式会社 新規抗癌剤
CN105985282B (zh) * 2015-01-28 2020-12-08 中国科学院广州生物医药与健康研究院 一种2-氧代-1,2-二氢苯并[cd]吲哚类化合物及其应用
CN109415444B (zh) 2016-07-29 2024-03-01 中外制药株式会社 显示增加的备选fviii辅因子功能活性的双特异性抗体
WO2018102006A1 (en) * 2016-11-30 2018-06-07 Ensemble Therapeutics Corporation Compounds for the inhibition of indoleamine-2,3-dioxygenase activity and use thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2508444B2 (ja) * 1987-06-25 1996-06-19 ソニー株式会社 カラ−陰極線管
KR20140145895A (ko) * 2013-06-14 2014-12-24 재단법인 의약바이오컨버젼스연구단 신규한 암 예방 또는 치료용 약학적 조성물

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Asian Journal of Chemistry, 4(3), (1992), pp.527-533 (1992.12.31.)* *
Bioorganic & Medicinal Chemistry Letters, 2012, 12, 5936-5941.* *
CANCER RESEARCH 42, (1982), pp.2115-2120 (1982.06.30.)* *
STN Registry Results* *
약학잡지 89(1), (1969), pp.98-103 (1969.12.31.)* *

Also Published As

Publication number Publication date
KR102520437B1 (ko) 2023-04-12
WO2020204548A1 (ko) 2020-10-08
US20220204497A1 (en) 2022-06-30
EP3939968A1 (en) 2022-01-19
EP3939968A4 (en) 2022-12-14
CN113874361A (zh) 2021-12-31
JP2022528950A (ja) 2022-06-16

Similar Documents

Publication Publication Date Title
US8461209B2 (en) Malonic acid sulfonamide derivative and pharmaceutical use thereof
US11478438B2 (en) Necrosis inhibitors
CA2972366C (en) Necrosis inhibitors
US10287243B2 (en) Sulfur derivatives as chemokine receptor modulators
ES2383239T3 (es) Compuestos de ácidos policíclicos útiles como antagonistas de CRTH2 y como agentes antialérgicos
US7166590B2 (en) Amino acid derivatives
EP2650287B9 (en) Thiazole Derivative and use thereof as VAP-1 Inhibitor
PT832061E (pt) Derivados de banzamida e sua utilizacao como antagonistas da vasopressina
SK12882001A3 (sk) Zlúčeniny a prípravky ako proteinázové inhibítory
WO1996018608A1 (fr) Derives d'aniline a activite inhibant la monoxyde d'azote synthase
EP0661266A1 (en) Substituted cyclic amine compounds as 5HT2 antagonists
WO2008053913A1 (fr) Dérivé de sulfonylurée capable d'inhiber sélectivement mmp-13
EA013083B1 (ru) Карбоксамидные производные в качестве антагонистов мускариновых рецепторов
WO2004087693A1 (en) Oxime derivatives and their use as pharmaceutically active agents
AU2017326611A1 (en) YAP1 inhibitors that target the interaction of YAP1 with Oct4
US6737425B1 (en) N,N-substituted cyclic amine derivatives
AU2019243141A1 (en) OX2R compounds
KR102520437B1 (ko) 항암활성을 갖는 신규한 화합물 및 이의 제조방법
ES2213563T3 (es) Compuestos de tiopirano como inhibidores de mmp.
JPH05221949A (ja) アミノ酸誘導体
US20130310384A1 (en) Sulfonamide-Containing Compounds
AU1890500A (en) Cyclic compound

Legal Events

Date Code Title Description
E902 Notification of reason for refusal
E902 Notification of reason for refusal
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant