ZA200404390B - 1,3-Diarylprop-2-en-1-ones, compositions containing same and use thereof. - Google Patents
1,3-Diarylprop-2-en-1-ones, compositions containing same and use thereof. Download PDFInfo
- Publication number
- ZA200404390B ZA200404390B ZA200404390A ZA200404390A ZA200404390B ZA 200404390 B ZA200404390 B ZA 200404390B ZA 200404390 A ZA200404390 A ZA 200404390A ZA 200404390 A ZA200404390 A ZA 200404390A ZA 200404390 B ZA200404390 B ZA 200404390B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- trimethoxyphenyl
- propenone
- product
- amino
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title description 3
- -1 COO(R4) Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 11
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
- CWLQUGTUXBXTLF-UHFFFAOYSA-N 1-methylpyrrolidin-1-ium-2-carboxylate Chemical compound CN1CCCC1C(O)=O CWLQUGTUXBXTLF-UHFFFAOYSA-N 0.000 claims description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 3
- 229960002449 glycine Drugs 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- CWLQUGTUXBXTLF-YFKPBYRVSA-N N-methylproline Chemical compound CN1CCC[C@H]1C(O)=O CWLQUGTUXBXTLF-YFKPBYRVSA-N 0.000 claims description 2
- 206010054094 Tumour necrosis Diseases 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 101100447171 Arabidopsis thaliana FRO2 gene Proteins 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000001737 promoting effect Effects 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- 102000004243 Tubulin Human genes 0.000 claims 1
- 108090000704 Tubulin Proteins 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 210000002889 endothelial cell Anatomy 0.000 claims 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- XDSHNNRBLSBDAP-UHFFFAOYSA-N (2E)-3-(3,4,5-trimethoxyphenyl)-2-propenal Natural products COC1=CC(C=CC=O)=CC(OC)=C1OC XDSHNNRBLSBDAP-UHFFFAOYSA-N 0.000 description 18
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 17
- 235000005513 chalcones Nutrition 0.000 description 17
- 150000001789 chalcones Chemical class 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000001093 anti-cancer Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002927 anti-mitotic effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- SPLCKLJETOKHHO-UHFFFAOYSA-N 2-amino-n-[2-methoxy-5-[2-methyl-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]phenyl]acetamide;hydrochloride Chemical compound Cl.C1=C(NC(=O)CN)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 SPLCKLJETOKHHO-UHFFFAOYSA-N 0.000 description 1
- RFNQYABMSQEIHT-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one Chemical compound COC1=CC=CC(C=CC(=O)C=2C=CC(O)=CC=2)=C1OC RFNQYABMSQEIHT-UHFFFAOYSA-N 0.000 description 1
- FDXAOGSVMCOTJP-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one Chemical compound COC1=CC=C(OC)C(C=CC(=O)C=2C=CC(O)=CC=2)=C1 FDXAOGSVMCOTJP-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical group C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- VPXSIAALWZMEKG-UHFFFAOYSA-N Cl.C1=C(NC(=O)C2N(CCC2)C)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 Chemical compound Cl.C1=C(NC(=O)C2N(CCC2)C)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 VPXSIAALWZMEKG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000003080 antimitotic agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
Classifications
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
- C07C279/32—N-nitroguanidines
- C07C279/36—Substituted N-nitroguanidines
-
- 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
- C07D207/10—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 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0115739A FR2833008B1 (fr) | 2001-12-05 | 2001-12-05 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404390B true ZA200404390B (en) | 2005-02-07 |
Family
ID=8870150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200404390A ZA200404390B (en) | 2001-12-05 | 2004-06-03 | 1,3-Diarylprop-2-en-1-ones, compositions containing same and use thereof. |
Country Status (4)
| Country | Link |
|---|---|
| FR (1) | FR2833008B1 (fr) |
| GT (1) | GT200200252A (fr) |
| NO (1) | NO20042803L (fr) |
| ZA (1) | ZA200404390B (fr) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
| EP0996432A2 (fr) * | 1997-06-26 | 2000-05-03 | Statens Seruminstitut | 1,3-bis-aromatique-prop-2-en-1-ones, 1,3-bis-aromatique-propane-1-ones et 1,3-bis-aromatique-prop-2-yn-1-ones a action biologique |
-
2001
- 2001-12-05 FR FR0115739A patent/FR2833008B1/fr not_active Expired - Fee Related
-
2002
- 2002-11-29 GT GT200200252A patent/GT200200252A/es unknown
-
2004
- 2004-06-03 ZA ZA200404390A patent/ZA200404390B/en unknown
- 2004-07-02 NO NO20042803A patent/NO20042803L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2833008A1 (fr) | 2003-06-06 |
| FR2833008B1 (fr) | 2004-05-21 |
| NO20042803L (no) | 2004-08-31 |
| GT200200252A (es) | 2003-11-11 |
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