CA2478540A1 - Indazoles substitues avec une activite anticancereuse - Google Patents

Info

Publication number

CA2478540A1

CA2478540A1 CA002478540A CA2478540A CA2478540A1 CA 2478540 A1 CA2478540 A1 CA 2478540A1 CA 002478540 A CA002478540 A CA 002478540A CA 2478540 A CA2478540 A CA 2478540A CA 2478540 A1 CA2478540 A1 CA 2478540A1

Authority

CA

Canada

Prior art keywords

indazol

phenyl

benzenesulfonamide

methanesulfonyl

methylsulfonyl

Prior art date

2002-03-11

Legal status (The legal status 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 status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000002473 indoazoles Chemical group 0.000 title abstract 4
• 230000001093 anti-cancer Effects 0.000 title description 6
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 45
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 45
• 238000004519 manufacturing process Methods 0.000 claims abstract description 3
• -1 6-(2-dimethylaminomethyl-5-methyl-morpholin-4-yl)-1H-benzimidazol-2-yl Chemical group 0.000 claims description 258
• 150000001875 compounds Chemical class 0.000 claims description 134
• 238000006243 chemical reaction Methods 0.000 claims description 54
• 239000002253 acid Substances 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 39
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000000217 alkyl group Chemical group 0.000 claims description 25
• 125000002947 alkylene group Chemical group 0.000 claims description 24
• 229940124530 sulfonamide Drugs 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000003107 substituted aryl group Chemical group 0.000 claims description 17
• 239000003112 inhibitor Substances 0.000 claims description 16
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 15
• 102100032311 Aurora kinase A Human genes 0.000 claims description 15
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 15
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 15
• 206010028980 Neoplasm Diseases 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• 101150001535 SRC gene Proteins 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 239000005711 Benzoic acid Substances 0.000 claims description 8
• 235000010233 benzoic acid Nutrition 0.000 claims description 8
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 8
• 229910052705 radium Inorganic materials 0.000 claims description 8
• 229910052701 rubidium Inorganic materials 0.000 claims description 8
• 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• IRYILYDRLZINJI-UHFFFAOYSA-N 3,4-dichloro-n-(3-methyl-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 IRYILYDRLZINJI-UHFFFAOYSA-N 0.000 claims description 6
• HGMGIWTWOLKILD-UHFFFAOYSA-N 3-fluoro-n-(3-methyl-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 HGMGIWTWOLKILD-UHFFFAOYSA-N 0.000 claims description 6
• SVOWCBCFXJLRIU-UHFFFAOYSA-N N-[3-(4-hydroxyphenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(O)=CC=3)C2=C1 SVOWCBCFXJLRIU-UHFFFAOYSA-N 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical group 0.000 claims description 6
• ZYRMFMZOLKOEFZ-UHFFFAOYSA-N n-[3-(3-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(N)C=CC=3)C2=C1 ZYRMFMZOLKOEFZ-UHFFFAOYSA-N 0.000 claims description 6
• FNTHMNHMNKDQEC-UHFFFAOYSA-N n-[3-(3-bromophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Br)C=CC=3)C2=C1 FNTHMNHMNKDQEC-UHFFFAOYSA-N 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• YNFJJRNYCSVSGB-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-naphthalen-1-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=CC=CC=C4C=CC=3)C2=C1 YNFJJRNYCSVSGB-UHFFFAOYSA-N 0.000 claims description 5
• LIMDSQLTBLQFLB-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-naphthalen-2-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4C=CC=CC4=CC=3)C2=C1 LIMDSQLTBLQFLB-UHFFFAOYSA-N 0.000 claims description 5
• MCLNQXKKMHFQLR-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-pyridin-3-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=NC=CC=3)C2=C1 MCLNQXKKMHFQLR-UHFFFAOYSA-N 0.000 claims description 5
• ZKDVCIAPCQMSJW-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-pyridin-4-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CN=CC=3)C2=C1 ZKDVCIAPCQMSJW-UHFFFAOYSA-N 0.000 claims description 5
• ZCVNZBOMBPHXHG-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-thiophen-2-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC=CC=3)C2=C1 ZCVNZBOMBPHXHG-UHFFFAOYSA-N 0.000 claims description 5
• SMCGMAXYINPFGK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC=CC=3)C2=C1 SMCGMAXYINPFGK-UHFFFAOYSA-N 0.000 claims description 5
• DWWIPKOTLDERIH-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethynyl)-2h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#CC=3C=CC=CC=3)C2=C1 DWWIPKOTLDERIH-UHFFFAOYSA-N 0.000 claims description 5
• SIHPXXPBIZDJGS-UHFFFAOYSA-N 3-fluoro-n-(3-iodo-2h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(I)=NNC3=CC=2)=C1 SIHPXXPBIZDJGS-UHFFFAOYSA-N 0.000 claims description 5
• SBSUSUMJNWUBRC-UHFFFAOYSA-N 3-fluoro-n-[3-(methanesulfonamido)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=C2C(NS(=O)(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 SBSUSUMJNWUBRC-UHFFFAOYSA-N 0.000 claims description 5
• MMBLKTXFYPXLON-UHFFFAOYSA-N 3-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 MMBLKTXFYPXLON-UHFFFAOYSA-N 0.000 claims description 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
• VRVWVMZURIDGGD-UHFFFAOYSA-N 4-amino-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 VRVWVMZURIDGGD-UHFFFAOYSA-N 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• YTCROYMIRGBRIQ-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(N)=O)C2=C1 YTCROYMIRGBRIQ-UHFFFAOYSA-N 0.000 claims description 5
• OZYAXQWHHTUDPI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 OZYAXQWHHTUDPI-UHFFFAOYSA-N 0.000 claims description 5
• 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims description 5
• 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims description 5
• PCAXMUPGGRFMOI-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 PCAXMUPGGRFMOI-UHFFFAOYSA-N 0.000 claims description 5
• PMZWMTCHDPQLFH-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]thiophene-2-sulfonamide Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4C=3)C2=CC=1NS(=O)(=O)C1=CC=CS1 PMZWMTCHDPQLFH-UHFFFAOYSA-N 0.000 claims description 5
• DYNFFHPGUWOLQT-UHFFFAOYSA-N N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C=1C2=CC(OC)=CC=C2NC=1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DYNFFHPGUWOLQT-UHFFFAOYSA-N 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• JIPJPRTZKUKIFK-UHFFFAOYSA-N n-(1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2)C2=C1 JIPJPRTZKUKIFK-UHFFFAOYSA-N 0.000 claims description 5
• MKZMSLHAPRHWEX-UHFFFAOYSA-N n-(3-anilino-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NC=3C=CC=CC=3)C2=C1 MKZMSLHAPRHWEX-UHFFFAOYSA-N 0.000 claims description 5
• YOHJWVZFKYKCFC-UHFFFAOYSA-N n-(6-methyl-3-phenyl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound C1=2C=C(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)C(C)=CC=2NN=C1C1=CC=CC=C1 YOHJWVZFKYKCFC-UHFFFAOYSA-N 0.000 claims description 5
• FMCKNGFTTFLGOF-XYOKQWHBSA-N n-[3-[(e)-2-(4-fluorophenyl)ethenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C=3C=CC(F)=CC=3)C2=C1 FMCKNGFTTFLGOF-XYOKQWHBSA-N 0.000 claims description 5
• AHFLNQASNRILFE-UHFFFAOYSA-N n-[3-[4-(dimethylamino)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(N(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O AHFLNQASNRILFE-UHFFFAOYSA-N 0.000 claims description 5
• BWAGAWVSXXJADX-UHFFFAOYSA-N n-[4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BWAGAWVSXXJADX-UHFFFAOYSA-N 0.000 claims description 5
• SBCCIIVYRCTELP-UHFFFAOYSA-N n-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SBCCIIVYRCTELP-UHFFFAOYSA-N 0.000 claims description 5
• RLTGXHOHVAGBFB-UHFFFAOYSA-N n-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NC(=O)C=3C=CC=CC=3)C2=C1 RLTGXHOHVAGBFB-UHFFFAOYSA-N 0.000 claims description 5
• MZXBVZRUPDXQCC-UHFFFAOYSA-N n-[5-[(3,5-difluorophenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC(F)=CC(F)=C1 MZXBVZRUPDXQCC-UHFFFAOYSA-N 0.000 claims description 5
• QADQJUPWUGQXEW-UHFFFAOYSA-N n-[5-[(3,5-difluorophenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 QADQJUPWUGQXEW-UHFFFAOYSA-N 0.000 claims description 5
• GFEQLGKQKXFMKV-UHFFFAOYSA-N n-[5-[(3-fluorophenyl)sulfonylamino]-1h-indazol-3-yl]acetamide Chemical compound C1=C2C(NC(=O)C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 GFEQLGKQKXFMKV-UHFFFAOYSA-N 0.000 claims description 5
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• SWWJMFAMHNRHOA-UHFFFAOYSA-N 2-methylsulfonyl-N-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC=CC=3)C2=C1 SWWJMFAMHNRHOA-UHFFFAOYSA-N 0.000 claims description 4
• NDTANLMIEUSSOH-UHFFFAOYSA-N 2-methylsulfonyl-N-[3-(1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=NC=CC=C4C=3)C2=C1 NDTANLMIEUSSOH-UHFFFAOYSA-N 0.000 claims description 4
• BFROGUGBGKIQPH-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BFROGUGBGKIQPH-UHFFFAOYSA-N 0.000 claims description 4
• VIKDGOBMESMILG-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-phenylsulfanyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2SC=3C=CC=CC=3)C2=C1 VIKDGOBMESMILG-UHFFFAOYSA-N 0.000 claims description 4
• BEPBFIIJPPVCKR-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-thiophen-3-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C3=CSC=C3)C2=C1 BEPBFIIJPPVCKR-UHFFFAOYSA-N 0.000 claims description 4
• HFNNFEGZWXXPSF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(2-trimethylsilylethynyl)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound C[Si](C)(C)C#CC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 HFNNFEGZWXXPSF-UHFFFAOYSA-N 0.000 claims description 4
• ZNDOQMZNKKWDTP-UHFFFAOYSA-N 3,4-dichloro-n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2)C2=C1 ZNDOQMZNKKWDTP-UHFFFAOYSA-N 0.000 claims description 4
• PYEANTVULAMRGV-UHFFFAOYSA-N 3-amino-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 PYEANTVULAMRGV-UHFFFAOYSA-N 0.000 claims description 4
• NCHATSXVPBRKKR-UHFFFAOYSA-N 3-fluoro-N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4NC5=CC=CC=C5C=4)=NNC3=CC=2)=C1 NCHATSXVPBRKKR-UHFFFAOYSA-N 0.000 claims description 4
• OHDWGXIIXQZSBW-UHFFFAOYSA-N 3-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 OHDWGXIIXQZSBW-UHFFFAOYSA-N 0.000 claims description 4
• YIMOCMSIWHYZRI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 YIMOCMSIWHYZRI-UHFFFAOYSA-N 0.000 claims description 4
• OYNKMNCGIOMAPL-UHFFFAOYSA-N 5-fluoro-2-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 OYNKMNCGIOMAPL-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• QSWHZRXINOGWDK-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2N)C2=C1 QSWHZRXINOGWDK-UHFFFAOYSA-N 0.000 claims description 4
• RGWZMNYEINMLSB-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 RGWZMNYEINMLSB-UHFFFAOYSA-N 0.000 claims description 4
• KMGGZTLYHGNAKE-UHFFFAOYSA-N n-(3-cyano-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C#N)C2=C1 KMGGZTLYHGNAKE-UHFFFAOYSA-N 0.000 claims description 4
• LOVSSJYJNHKBJF-UHFFFAOYSA-N n-(3-cyano-1h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C#N)=NNC3=CC=2)=C1 LOVSSJYJNHKBJF-UHFFFAOYSA-N 0.000 claims description 4
• QMKOXXIAWGTJLB-UHFFFAOYSA-N n-(3-methyl-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O QMKOXXIAWGTJLB-UHFFFAOYSA-N 0.000 claims description 4
• ASNSAHHPIBUMQH-UHFFFAOYSA-N n-[3-(1-benzothiophen-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC4=CC=CC=C4C=3)C2=C1 ASNSAHHPIBUMQH-UHFFFAOYSA-N 0.000 claims description 4
• RGMSNJXLLHBCGD-UHFFFAOYSA-N n-[3-(1-benzothiophen-3-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=CC=CC=C4SC=3)C2=C1 RGMSNJXLLHBCGD-UHFFFAOYSA-N 0.000 claims description 4
• PTJURHKDEQOFKR-UHFFFAOYSA-N n-[3-(2-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)N)C2=C1 PTJURHKDEQOFKR-UHFFFAOYSA-N 0.000 claims description 4
• DUICGHQOLRZWJD-UHFFFAOYSA-N n-[3-(4-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(F)=CC=3)C2=C1 DUICGHQOLRZWJD-UHFFFAOYSA-N 0.000 claims description 4
• RIBHGAYUTBNLNI-UHFFFAOYSA-N n-[3-(4-methoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 RIBHGAYUTBNLNI-UHFFFAOYSA-N 0.000 claims description 4
• IAKJPIODQWXTDR-XYOKQWHBSA-N n-[3-[(e)-2-(4-chlorophenyl)ethenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C=3C=CC(Cl)=CC=3)C2=C1 IAKJPIODQWXTDR-XYOKQWHBSA-N 0.000 claims description 4
• PPPRVPAMLGCCFM-UHFFFAOYSA-N n-[5-[(3-fluorophenyl)sulfonylamino]-1h-indazol-3-yl]benzamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(NC(=O)C=4C=CC=CC=4)=NNC3=CC=2)=C1 PPPRVPAMLGCCFM-UHFFFAOYSA-N 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• KMWBIKVAWJEHCX-UHFFFAOYSA-N 1h-indazol-5-yl 3-fluorobenzenesulfonate Chemical compound FC1=CC=CC(S(=O)(=O)OC=2C=C3C=NNC3=CC=2)=C1 KMWBIKVAWJEHCX-UHFFFAOYSA-N 0.000 claims description 3
• PUXKJVPVEYPABV-UHFFFAOYSA-N 2-methylsulfonyl-n-(3-quinolin-8-yl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C4=NC=CC=C4C=CC=3)C2=C1 PUXKJVPVEYPABV-UHFFFAOYSA-N 0.000 claims description 3
• CXONENHLWWEXSE-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-nitrophenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(=CC=3)[N+]([O-])=O)C2=C1 CXONENHLWWEXSE-UHFFFAOYSA-N 0.000 claims description 3
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• VXXKAGRYQZLBNS-UHFFFAOYSA-N 3,4-dichloro-n-(3-chloro-2h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(Cl)=NNC2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 VXXKAGRYQZLBNS-UHFFFAOYSA-N 0.000 claims description 3
• GHJIYUWSHCZVFW-UHFFFAOYSA-N 3,4-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 GHJIYUWSHCZVFW-UHFFFAOYSA-N 0.000 claims description 3
• DMRVOBLLZGFOIS-UHFFFAOYSA-N 3-fluoro-n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C=NNC3=CC=2)=C1 DMRVOBLLZGFOIS-UHFFFAOYSA-N 0.000 claims description 3
• XVCOPODOXQGYFA-UHFFFAOYSA-N 3-fluoro-n-(3-oxo-1,2-dihydroindazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 XVCOPODOXQGYFA-UHFFFAOYSA-N 0.000 claims description 3
• YQWKKTMDPYCPOE-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfonylamino]-n-phenyl-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(=O)NC=3C=CC=CC=3)C2=C1 YQWKKTMDPYCPOE-UHFFFAOYSA-N 0.000 claims description 3
• ATXMCKZTGVVYJO-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-n-phenyl-1h-indazole-3-carboxamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(C(=O)NC=4C=CC=CC=4)=NNC3=CC=2)=C1 ATXMCKZTGVVYJO-UHFFFAOYSA-N 0.000 claims description 3
• PPHVRPNSDQPTQP-UHFFFAOYSA-N N-[3-(1H-benzimidazol-2-yl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4N=3)C2=C1 PPHVRPNSDQPTQP-UHFFFAOYSA-N 0.000 claims description 3
• WMGQUWSQDYYQSI-UHFFFAOYSA-N n-(3-bromo-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2Br)C2=C1 WMGQUWSQDYYQSI-UHFFFAOYSA-N 0.000 claims description 3
• QXMQCLOJLMJUBM-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-3-fluorobenzenesulfonamide Chemical compound FC1=CC=CC(S(=O)(=O)NC=2C=C3C(Cl)=NNC3=CC=2)=C1 QXMQCLOJLMJUBM-UHFFFAOYSA-N 0.000 claims description 3
• URVXYUWODGMOLS-UHFFFAOYSA-N n-(3-fluorophenyl)-1h-indazole-5-sulfonamide Chemical compound FC1=CC=CC(NS(=O)(=O)C=2C=C3C=NNC3=CC=2)=C1 URVXYUWODGMOLS-UHFFFAOYSA-N 0.000 claims description 3
• YLTLNEMPCOXATC-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)cyclohexanesulfonamide Chemical compound C1CCCCC1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 YLTLNEMPCOXATC-UHFFFAOYSA-N 0.000 claims description 3
• IBXPTSRLYBPVJO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)piperidine-4-sulfonamide Chemical compound C1CNCCC1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 IBXPTSRLYBPVJO-UHFFFAOYSA-N 0.000 claims description 3
• JWUZPUPHDYPCQO-UHFFFAOYSA-N n-[3-(1h-indol-5-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4C=CNC4=CC=3)C2=C1 JWUZPUPHDYPCQO-UHFFFAOYSA-N 0.000 claims description 3
• NPGAKZNWLQYIBR-UHFFFAOYSA-N n-[3-(3,5-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C=C(F)C=3)C2=C1 NPGAKZNWLQYIBR-UHFFFAOYSA-N 0.000 claims description 3
• RPJDAUSWEFFJMQ-UHFFFAOYSA-N n-[3-(3-cyanophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=CC=3)C#N)C2=C1 RPJDAUSWEFFJMQ-UHFFFAOYSA-N 0.000 claims description 3
• RHCLDPILTWUHCJ-UHFFFAOYSA-N n-[3-(4-aminophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(N)=CC=3)C2=C1 RHCLDPILTWUHCJ-UHFFFAOYSA-N 0.000 claims description 3
• VYBIMAFGLAQRCL-UHFFFAOYSA-N n-[3-(4-chlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(Cl)=CC=3)C2=C1 VYBIMAFGLAQRCL-UHFFFAOYSA-N 0.000 claims description 3
• ZIQNKRBWHDSEKD-UHFFFAOYSA-N n-[3-(benzylamino)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2NCC=3C=CC=CC=3)C2=C1 ZIQNKRBWHDSEKD-UHFFFAOYSA-N 0.000 claims description 3
• KRGGUWOXZSQAQR-UHFFFAOYSA-N n-[3-(methylamino)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C2C(NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O KRGGUWOXZSQAQR-UHFFFAOYSA-N 0.000 claims description 3
• GXXHQJGQROXUDO-UHFFFAOYSA-N n-[3-[2-(4-chlorophenyl)ethyl]-2h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC(Cl)=CC=3)C2=C1 GXXHQJGQROXUDO-UHFFFAOYSA-N 0.000 claims description 3
• SGZMDYMDGSNYSI-UHFFFAOYSA-N n-[3-[2-(4-fluorophenyl)ethyl]-2h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2CCC=3C=CC(F)=CC=3)C2=C1 SGZMDYMDGSNYSI-UHFFFAOYSA-N 0.000 claims description 3
• IFKZYHVPGFGFHB-UHFFFAOYSA-N n-[3-[3,5-bis(trifluoromethyl)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=C(C=3)C(F)(F)F)C(F)(F)F)C2=C1 IFKZYHVPGFGFHB-UHFFFAOYSA-N 0.000 claims description 3
• SQFAUZVASKEZAB-UHFFFAOYSA-N n-cyclohexyl-5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(=O)NC3CCCCC3)C2=C1 SQFAUZVASKEZAB-UHFFFAOYSA-N 0.000 claims description 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• QHMSFAPYDLUZAX-UHFFFAOYSA-N 1-phenyl-n-(3-phenyl-1h-indazol-5-yl)methanesulfonamide Chemical compound C=1C=C2NN=C(C=3C=CC=CC=3)C2=CC=1NS(=O)(=O)CC1=CC=CC=C1 QHMSFAPYDLUZAX-UHFFFAOYSA-N 0.000 claims description 2
• HEOXSYYWDQPVFL-UHFFFAOYSA-N 2,4,6-trimethyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 HEOXSYYWDQPVFL-UHFFFAOYSA-N 0.000 claims description 2
• TVOKDUKBWNSZBZ-UHFFFAOYSA-N 2,5-dimethoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 TVOKDUKBWNSZBZ-UHFFFAOYSA-N 0.000 claims description 2
• AHEXHEDIBDQUDB-UHFFFAOYSA-N 2-amino-4,6-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound NC1=CC(Cl)=CC(Cl)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AHEXHEDIBDQUDB-UHFFFAOYSA-N 0.000 claims description 2
• YTNFPOJQWPBMMP-UHFFFAOYSA-N 2-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound BrC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 YTNFPOJQWPBMMP-UHFFFAOYSA-N 0.000 claims description 2
• NXZJFILFGTVFPE-UHFFFAOYSA-N 2-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC=C(C#N)C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 NXZJFILFGTVFPE-UHFFFAOYSA-N 0.000 claims description 2
• FJINAFTWNKWKBW-UHFFFAOYSA-N 2-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 FJINAFTWNKWKBW-UHFFFAOYSA-N 0.000 claims description 2
• AYXXVVZVJYNNPU-UHFFFAOYSA-N 2-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AYXXVVZVJYNNPU-UHFFFAOYSA-N 0.000 claims description 2
• LVMHHFIKGBLGFK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)C=3C=CC=CC=3)C2=C1 LVMHHFIKGBLGFK-UHFFFAOYSA-N 0.000 claims description 2
• RSHWLECTDYHGLL-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-nitrophenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=CC=3)[N+]([O-])=O)C2=C1 RSHWLECTDYHGLL-UHFFFAOYSA-N 0.000 claims description 2
• USBADQQPQWYQNJ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-propan-2-ylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CC(C)C1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 USBADQQPQWYQNJ-UHFFFAOYSA-N 0.000 claims description 2
• MLPQRVYXVYSDLT-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-phenylmethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C2=C1 MLPQRVYXVYSDLT-UHFFFAOYSA-N 0.000 claims description 2
• QGXBDXOTTZFQNQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-phenylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(=CC=3)C=3C=CC=CC=3)C2=C1 QGXBDXOTTZFQNQ-UHFFFAOYSA-N 0.000 claims description 2
• YAKQQGZGXXBXTG-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-propan-2-ylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O YAKQQGZGXXBXTG-UHFFFAOYSA-N 0.000 claims description 2
• JJANLNUFRDPPOF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(trifluoromethoxy)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(OC(F)(F)F)C=CC=3)C2=C1 JJANLNUFRDPPOF-UHFFFAOYSA-N 0.000 claims description 2
• FNJCYRVTGGSQDJ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[3-(trifluoromethyl)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(C=CC=3)C(F)(F)F)C2=C1 FNJCYRVTGGSQDJ-UHFFFAOYSA-N 0.000 claims description 2
• JWDKHFWPMQFBIF-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[4-(trifluoromethoxy)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OC(F)(F)F)=CC=3)C2=C1 JWDKHFWPMQFBIF-UHFFFAOYSA-N 0.000 claims description 2
• RZZHWULQKJRTKR-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-[4-(trifluoromethyl)phenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(=CC=3)C(F)(F)F)C2=C1 RZZHWULQKJRTKR-UHFFFAOYSA-N 0.000 claims description 2
• UIWNKYKRLSWDPY-UHFFFAOYSA-N 2-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 UIWNKYKRLSWDPY-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• AWDBPTWYGUHHIQ-UHFFFAOYSA-N 3,4-difluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=C(F)C(F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 AWDBPTWYGUHHIQ-UHFFFAOYSA-N 0.000 claims description 2
• AEGKEYKEZSJHPN-UHFFFAOYSA-N 3,5-dichloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 AEGKEYKEZSJHPN-UHFFFAOYSA-N 0.000 claims description 2
• GCDSZNYNEYHZNO-UHFFFAOYSA-N 3,5-difluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound FC1=CC(F)=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 GCDSZNYNEYHZNO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• DLPPBHICRMSCBX-UHFFFAOYSA-N 3-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 DLPPBHICRMSCBX-UHFFFAOYSA-N 0.000 claims description 2
• NFAHTVPEUUBFJT-UHFFFAOYSA-N 3-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound BrC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 NFAHTVPEUUBFJT-UHFFFAOYSA-N 0.000 claims description 2
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
• RNGAJCCTBJROOM-UHFFFAOYSA-N 3-chloro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 RNGAJCCTBJROOM-UHFFFAOYSA-N 0.000 claims description 2
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
• MBBXLIKTDIUXCA-UHFFFAOYSA-N 3-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC(C#N)=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MBBXLIKTDIUXCA-UHFFFAOYSA-N 0.000 claims description 2
• FKYAGRQAAOKMNJ-UHFFFAOYSA-N 3-methoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound COC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 FKYAGRQAAOKMNJ-UHFFFAOYSA-N 0.000 claims description 2
• YMZDSSYFEHDUGO-UHFFFAOYSA-N 3-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 YMZDSSYFEHDUGO-UHFFFAOYSA-N 0.000 claims description 2
• ASSDOTHJONORNL-UHFFFAOYSA-N 3-phenyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 ASSDOTHJONORNL-UHFFFAOYSA-N 0.000 claims description 2
• ISLSMVXTGAQGMN-UHFFFAOYSA-N 4-bromo-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 ISLSMVXTGAQGMN-UHFFFAOYSA-N 0.000 claims description 2
• GMUDJTSSYZZRNB-UHFFFAOYSA-N 4-butoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(OCCCC)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 GMUDJTSSYZZRNB-UHFFFAOYSA-N 0.000 claims description 2
• MYCDWAKLELQQAC-UHFFFAOYSA-N 4-cyano-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MYCDWAKLELQQAC-UHFFFAOYSA-N 0.000 claims description 2
• LNTRMSKQNAYDND-UHFFFAOYSA-N 4-fluoro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 LNTRMSKQNAYDND-UHFFFAOYSA-N 0.000 claims description 2
• QESTUIHZQQVWEL-UHFFFAOYSA-N 4-methoxy-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 QESTUIHZQQVWEL-UHFFFAOYSA-N 0.000 claims description 2
• XGPRBTMLIATVFT-UHFFFAOYSA-N 4-methyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 XGPRBTMLIATVFT-UHFFFAOYSA-N 0.000 claims description 2
• PEUDUYPQHUABPX-UHFFFAOYSA-N 4-nitro-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 PEUDUYPQHUABPX-UHFFFAOYSA-N 0.000 claims description 2
• UWMIBHKZTFDAMN-UHFFFAOYSA-N 4-tert-butyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 UWMIBHKZTFDAMN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
• MEWNTBNDVVRICG-UHFFFAOYSA-N 5-(dibutylamino)-n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(CCCC)CCCC)=CC=CC2=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 MEWNTBNDVVRICG-UHFFFAOYSA-N 0.000 claims description 2
• PGKIBDXZMQYKSC-UHFFFAOYSA-N 5-(dimethylamino)-n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 PGKIBDXZMQYKSC-UHFFFAOYSA-N 0.000 claims description 2
• JXOMJPQNUVDBQR-UHFFFAOYSA-N 5-chloro-n-(3-phenyl-1h-indazol-5-yl)thiophene-2-sulfonamide Chemical compound S1C(Cl)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 JXOMJPQNUVDBQR-UHFFFAOYSA-N 0.000 claims description 2
• 101001034652 Homo sapiens Insulin-like growth factor 1 receptor Proteins 0.000 claims description 2
• 102100039688 Insulin-like growth factor 1 receptor Human genes 0.000 claims description 2
• ZYRQIKVFBFGSTC-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]-2-(trifluoromethoxy)benzenesulfonamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 ZYRQIKVFBFGSTC-UHFFFAOYSA-N 0.000 claims description 2
• SGKZMHSWJVCVNB-UHFFFAOYSA-N N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4C=3)C2=CC=1NS(=O)(=O)C1=CC=CC=C1 SGKZMHSWJVCVNB-UHFFFAOYSA-N 0.000 claims description 2
• IABVUQZTRBAVOA-UHFFFAOYSA-N N-[3-(4-hydroxyphenyl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(O)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 IABVUQZTRBAVOA-UHFFFAOYSA-N 0.000 claims description 2
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• MYZXIZXWICYCBX-UHFFFAOYSA-N n-(1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=C2NN=CC2=CC=1NS(=O)(=O)C1=CC=CC=C1 MYZXIZXWICYCBX-UHFFFAOYSA-N 0.000 claims description 2
• JPJLFYPICGORTG-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2,6-dichlorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl JPJLFYPICGORTG-UHFFFAOYSA-N 0.000 claims description 2
• HHZVBQIWQWPJSC-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-2,6-difluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=C(F)C=CC=C1F HHZVBQIWQWPJSC-UHFFFAOYSA-N 0.000 claims description 2
• LNHVNMRKXSHDLT-UHFFFAOYSA-N n-(3-amino-1h-indazol-5-yl)-3,5-difluorobenzenesulfonamide Chemical compound C1=C2C(N)=NNC2=CC=C1NS(=O)(=O)C1=CC(F)=CC(F)=C1 LNHVNMRKXSHDLT-UHFFFAOYSA-N 0.000 claims description 2
• RBVQLBDPNPEWPJ-UHFFFAOYSA-N n-(3-chloro-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2Cl)C2=C1 RBVQLBDPNPEWPJ-UHFFFAOYSA-N 0.000 claims description 2
• JJAIABXSZLBNFY-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2-(trifluoromethoxy)benzenesulfonamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 JJAIABXSZLBNFY-UHFFFAOYSA-N 0.000 claims description 2
• ZYZUSUWQGWCKBQ-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 ZYZUSUWQGWCKBQ-UHFFFAOYSA-N 0.000 claims description 2
• VDDFGASEUCSXLO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 VDDFGASEUCSXLO-UHFFFAOYSA-N 0.000 claims description 2
• GXCMRLNIRSKEDW-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)butane-1-sulfonamide Chemical compound C12=CC(NS(=O)(=O)CCCC)=CC=C2NN=C1C1=CC=CC=C1 GXCMRLNIRSKEDW-UHFFFAOYSA-N 0.000 claims description 2
• OMENKMXQXAHGCN-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)ethanesulfonamide Chemical compound C12=CC(NS(=O)(=O)CC)=CC=C2NN=C1C1=CC=CC=C1 OMENKMXQXAHGCN-UHFFFAOYSA-N 0.000 claims description 2
• YOWRWXSRPMACOW-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)methanesulfonamide Chemical compound C12=CC(NS(=O)(=O)C)=CC=C2NN=C1C1=CC=CC=C1 YOWRWXSRPMACOW-UHFFFAOYSA-N 0.000 claims description 2
• NBVACTMTKZIYCG-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)naphthalene-1-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 NBVACTMTKZIYCG-UHFFFAOYSA-N 0.000 claims description 2
• ZGGFGSXSGDVOHL-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 ZGGFGSXSGDVOHL-UHFFFAOYSA-N 0.000 claims description 2
• ZYLXQFKSXMAKBO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)propane-1-sulfonamide Chemical compound C12=CC(NS(=O)(=O)CCC)=CC=C2NN=C1C1=CC=CC=C1 ZYLXQFKSXMAKBO-UHFFFAOYSA-N 0.000 claims description 2
• LHUZDSHMEIXBJE-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)propane-2-sulfonamide Chemical compound C12=CC(NS(=O)(=O)C(C)C)=CC=C2NN=C1C1=CC=CC=C1 LHUZDSHMEIXBJE-UHFFFAOYSA-N 0.000 claims description 2
• XDINTPYWJPNKFO-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)pyridine-3-sulfonamide Chemical compound C=1C=CN=CC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 XDINTPYWJPNKFO-UHFFFAOYSA-N 0.000 claims description 2
• JITLNYHEWIRGHR-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)quinoline-8-sulfonamide Chemical compound C=1C=CC2=CC=CN=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 JITLNYHEWIRGHR-UHFFFAOYSA-N 0.000 claims description 2
• UBDFYNJUKQCRLU-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 UBDFYNJUKQCRLU-UHFFFAOYSA-N 0.000 claims description 2
• NNFNZBCXJLVDEI-UHFFFAOYSA-N n-[2-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NNFNZBCXJLVDEI-UHFFFAOYSA-N 0.000 claims description 2
• NZHWWAMEEIBHOC-UHFFFAOYSA-N n-[2-chloro-4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]phenyl]acetamide Chemical compound C1=C(Cl)C(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 NZHWWAMEEIBHOC-UHFFFAOYSA-N 0.000 claims description 2
• JBKSWEGPKPCXMZ-UHFFFAOYSA-N n-[3-(2,3-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=C(Cl)C=CC=3)Cl)C2=C1 JBKSWEGPKPCXMZ-UHFFFAOYSA-N 0.000 claims description 2
• BIHARHJDKGIJHV-UHFFFAOYSA-N n-[3-(2,3-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=C(F)C=CC=3)F)C2=C1 BIHARHJDKGIJHV-UHFFFAOYSA-N 0.000 claims description 2
• IAJWJRZRIUSJEA-UHFFFAOYSA-N n-[3-(2,4-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC(Cl)=CC=3)Cl)C2=C1 IAJWJRZRIUSJEA-UHFFFAOYSA-N 0.000 claims description 2
• MPQHPKGSKGAKLU-UHFFFAOYSA-N n-[3-(2,4-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC(F)=CC=3)F)C2=C1 MPQHPKGSKGAKLU-UHFFFAOYSA-N 0.000 claims description 2
• YZLPNORYSLGVHH-UHFFFAOYSA-N n-[3-(2,5-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=C(Cl)C=3)Cl)C2=C1 YZLPNORYSLGVHH-UHFFFAOYSA-N 0.000 claims description 2
• WBVMJGPSZULOJH-UHFFFAOYSA-N n-[3-(2-chlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)Cl)C2=C1 WBVMJGPSZULOJH-UHFFFAOYSA-N 0.000 claims description 2
• FOAWJAYNKAANKE-UHFFFAOYSA-N n-[3-(2-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CCOC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O FOAWJAYNKAANKE-UHFFFAOYSA-N 0.000 claims description 2
• SMKHTFVESRLGHO-UHFFFAOYSA-N n-[3-(2-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)F)C2=C1 SMKHTFVESRLGHO-UHFFFAOYSA-N 0.000 claims description 2
• HDBSRDZTTSIXIP-UHFFFAOYSA-N n-[3-(3,4-difluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(F)=CC=3)C2=C1 HDBSRDZTTSIXIP-UHFFFAOYSA-N 0.000 claims description 2
• LQIMQNSGGIKOLD-UHFFFAOYSA-N n-[3-(3,5-dibromophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Br)C=C(Br)C=3)C2=C1 LQIMQNSGGIKOLD-UHFFFAOYSA-N 0.000 claims description 2
• YZVWRZCVYIMXAQ-UHFFFAOYSA-N n-[3-(3,5-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C=C(Cl)C=3)C2=C1 YZVWRZCVYIMXAQ-UHFFFAOYSA-N 0.000 claims description 2
• JBINBXKUSLUOMD-UHFFFAOYSA-N n-[3-(3-amino-4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(N)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JBINBXKUSLUOMD-UHFFFAOYSA-N 0.000 claims description 2
• OMIYKMMBVIXKHL-UHFFFAOYSA-N n-[3-(3-chloro-4-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C(F)=CC=3)C2=C1 OMIYKMMBVIXKHL-UHFFFAOYSA-N 0.000 claims description 2
• QEGXBKGEGHWADH-UHFFFAOYSA-N n-[3-(3-chlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C=CC=3)C2=C1 QEGXBKGEGHWADH-UHFFFAOYSA-N 0.000 claims description 2
• TZZUSSGJZPHVNK-UHFFFAOYSA-N n-[3-(3-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CCOC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 TZZUSSGJZPHVNK-UHFFFAOYSA-N 0.000 claims description 2
• YACPJGJIMXFDCL-UHFFFAOYSA-N n-[3-(3-fluoro-4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O YACPJGJIMXFDCL-UHFFFAOYSA-N 0.000 claims description 2
• WZFXZBMHETWPTR-UHFFFAOYSA-N n-[3-(3-fluoro-4-phenylmethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(OCC=4C=CC=CC=4)=CC=3)C2=C1 WZFXZBMHETWPTR-UHFFFAOYSA-N 0.000 claims description 2
• OAYZGFLQGYKHCY-UHFFFAOYSA-N n-[3-(3-fluoro-4-phenylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C(=CC=3)C=3C=CC=CC=3)C2=C1 OAYZGFLQGYKHCY-UHFFFAOYSA-N 0.000 claims description 2
• HTCQLMOFRKPKNH-UHFFFAOYSA-N n-[3-(3-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(F)C=CC=3)C2=C1 HTCQLMOFRKPKNH-UHFFFAOYSA-N 0.000 claims description 2
• GEAMSRBTHPOHNR-UHFFFAOYSA-N n-[3-(3-hydroxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(O)C=CC=3)C2=C1 GEAMSRBTHPOHNR-UHFFFAOYSA-N 0.000 claims description 2
• SMJFTRJYUSRUOW-UHFFFAOYSA-N n-[3-(4-acetylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SMJFTRJYUSRUOW-UHFFFAOYSA-N 0.000 claims description 2
• QFOFSLSNTUGTRG-UHFFFAOYSA-N n-[3-(4-bromo-2-fluorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC(Br)=CC=3)F)C2=C1 QFOFSLSNTUGTRG-UHFFFAOYSA-N 0.000 claims description 2
• HKODFKUTKSMUEP-UHFFFAOYSA-N n-[3-(4-bromophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(Br)=CC=3)C2=C1 HKODFKUTKSMUEP-UHFFFAOYSA-N 0.000 claims description 2
• MTDMFUNNGODSRH-UHFFFAOYSA-N n-[3-(4-cyanophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(=CC=3)C#N)C2=C1 MTDMFUNNGODSRH-UHFFFAOYSA-N 0.000 claims description 2
• ISKOFTNXFMOPFL-UHFFFAOYSA-N n-[3-(4-ethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(OCC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ISKOFTNXFMOPFL-UHFFFAOYSA-N 0.000 claims description 2
• BUXMPVOERLWGKB-UHFFFAOYSA-N n-[3-(4-ethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(CC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O BUXMPVOERLWGKB-UHFFFAOYSA-N 0.000 claims description 2
• ZNGWPKMDFWSAAW-UHFFFAOYSA-N n-[3-(4-ethylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(SCC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ZNGWPKMDFWSAAW-UHFFFAOYSA-N 0.000 claims description 2
• BBHBFINEYAASLC-UHFFFAOYSA-N n-[3-(4-fluoro-3-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(F)C(C)=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 BBHBFINEYAASLC-UHFFFAOYSA-N 0.000 claims description 2
• ITDOJSMVXLAUMO-UHFFFAOYSA-N n-[3-(5-chloro-2-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=C(Cl)C=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ITDOJSMVXLAUMO-UHFFFAOYSA-N 0.000 claims description 2
• HQMBGNCSEQODPO-UHFFFAOYSA-N n-[3-(5-chlorothiophen-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3SC(Cl)=CC=3)C2=C1 HQMBGNCSEQODPO-UHFFFAOYSA-N 0.000 claims description 2
• OVBQYGLDWDCWNO-UHFFFAOYSA-N n-[3-(furan-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3OC=CC=3)C2=C1 OVBQYGLDWDCWNO-UHFFFAOYSA-N 0.000 claims description 2
• IKKQTWNLZGTAEZ-UHFFFAOYSA-N n-[3-(furan-3-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C3=COC=C3)C2=C1 IKKQTWNLZGTAEZ-UHFFFAOYSA-N 0.000 claims description 2
• LCBVNGRMXSDLHL-UHFFFAOYSA-N n-[3-[4-(hydroxymethyl)phenyl]-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(CO)=CC=3)C2=C1 LCBVNGRMXSDLHL-UHFFFAOYSA-N 0.000 claims description 2
• HZMDTNRQCKTTHY-UHFFFAOYSA-N n-[[5-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]thiophen-2-yl]methyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCC(S1)=CC=C1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 HZMDTNRQCKTTHY-UHFFFAOYSA-N 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
• JNGGVHJURWJQIO-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2,3,4-trimethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JNGGVHJURWJQIO-UHFFFAOYSA-N 0.000 claims 1
• NNGMCAGGKGJHJA-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(3-phenylmethoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(OCC=4C=CC=CC=4)C=CC=3)C2=C1 NNGMCAGGKGJHJA-UHFFFAOYSA-N 0.000 claims 1
• JHBIJSRTJQYQKQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-methylsulfonylphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O JHBIJSRTJQYQKQ-UHFFFAOYSA-N 0.000 claims 1
• RDNBAGLXYHDJPZ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(4-phenoxyphenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(OC=4C=CC=CC=4)=CC=3)C2=C1 RDNBAGLXYHDJPZ-UHFFFAOYSA-N 0.000 claims 1
• SMXAPCOWDIDWOP-ACCUITESSA-N 2-methylsulfonyl-n-[3-[(e)-2-phenylethenyl]-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C=3C=CC=CC=3)C2=C1 SMXAPCOWDIDWOP-ACCUITESSA-N 0.000 claims 1
• SFOTVLKIYVFVPN-UHFFFAOYSA-N 4-(dimethylamino)-2,3,5,6-tetrafluoro-N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide Chemical compound FC1=C(F)C(N(C)C)=C(F)C(F)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3NC4=CC=CC=C4C=3)C2=C1 SFOTVLKIYVFVPN-UHFFFAOYSA-N 0.000 claims 1
• DKELXIARPSFBFA-UHFFFAOYSA-N 4-methylsulfonyl-n-(3-phenyl-1h-indazol-5-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 DKELXIARPSFBFA-UHFFFAOYSA-N 0.000 claims 1
• XZAWZBNJMXXCGU-UHFFFAOYSA-N 5-(dimethylamino)-n-[3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazol-3-yl]phenyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(C=1)=CC=CC=1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XZAWZBNJMXXCGU-UHFFFAOYSA-N 0.000 claims 1
• 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 claims 1
• ZYHXLDWPAFQSBX-UHFFFAOYSA-N n-(3-dibenzofuran-4-yl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=4OC5=CC=CC=C5C=4C=CC=3)C2=C1 ZYHXLDWPAFQSBX-UHFFFAOYSA-N 0.000 claims 1
• QAPBXCRWMOFRGY-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C=1C=CC2=NON=C2C=1S(=O)(=O)NC(C=C12)=CC=C1NN=C2C1=CC=CC=C1 QAPBXCRWMOFRGY-UHFFFAOYSA-N 0.000 claims 1
• BDVIRPJEWYQGRA-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-2,4,6-tri(propan-2-yl)benzenesulfonamide Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 BDVIRPJEWYQGRA-UHFFFAOYSA-N 0.000 claims 1
• JVDZRLPOHNQBGG-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)=C1 JVDZRLPOHNQBGG-UHFFFAOYSA-N 0.000 claims 1
• RAXAXMSLIFDADE-UHFFFAOYSA-N n-(3-phenyl-1h-indazol-5-yl)-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC=CC=3)C2=C1 RAXAXMSLIFDADE-UHFFFAOYSA-N 0.000 claims 1
• ZLJBLVFGMNVLET-UHFFFAOYSA-N n-[3-(1,3-benzodioxol-5-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C4OCOC4=CC=3)C2=C1 ZLJBLVFGMNVLET-UHFFFAOYSA-N 0.000 claims 1
• WTLTTWVXFUEYKG-UHFFFAOYSA-N n-[3-(1-benzofuran-2-yl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3OC4=CC=CC=C4C=3)C2=C1 WTLTTWVXFUEYKG-UHFFFAOYSA-N 0.000 claims 1
• UGGDZFSYLDVITK-UHFFFAOYSA-N n-[3-(2,4-dimethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O UGGDZFSYLDVITK-UHFFFAOYSA-N 0.000 claims 1
• CPVUKBOFNWWCSE-UHFFFAOYSA-N n-[3-(2-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O CPVUKBOFNWWCSE-UHFFFAOYSA-N 0.000 claims 1
• HPJXAQPXNLNSDK-UHFFFAOYSA-N n-[3-(2-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O HPJXAQPXNLNSDK-UHFFFAOYSA-N 0.000 claims 1
• DRWVAUBIGFVVMW-UHFFFAOYSA-N n-[3-(2-methylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CSC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O DRWVAUBIGFVVMW-UHFFFAOYSA-N 0.000 claims 1
• BGKQTLKBCDFZKF-UHFFFAOYSA-N n-[3-(3,4-dichlorophenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=C(Cl)C(Cl)=CC=3)C2=C1 BGKQTLKBCDFZKF-UHFFFAOYSA-N 0.000 claims 1
• SUXDTEGXADFEQM-UHFFFAOYSA-N n-[3-(3,4-dimethoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SUXDTEGXADFEQM-UHFFFAOYSA-N 0.000 claims 1
• ONUUMGWRZNISBW-UHFFFAOYSA-N n-[3-(3,4-dimethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=C(C)C(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O ONUUMGWRZNISBW-UHFFFAOYSA-N 0.000 claims 1
• XADFFBXSZLKBNH-UHFFFAOYSA-N n-[3-(3,5-dimethylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC(C)=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 XADFFBXSZLKBNH-UHFFFAOYSA-N 0.000 claims 1
• QSSHFLOHMTUJSF-UHFFFAOYSA-N n-[3-(3-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound COC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 QSSHFLOHMTUJSF-UHFFFAOYSA-N 0.000 claims 1
• OGRWMAOQGQIXJV-UHFFFAOYSA-N n-[3-(3-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CC1=CC=CC(C=2C3=CC(NS(=O)(=O)C=4C(=CC=CC=4)S(C)(=O)=O)=CC=C3NN=2)=C1 OGRWMAOQGQIXJV-UHFFFAOYSA-N 0.000 claims 1
• CYYGWWYXMYBLCX-UHFFFAOYSA-N n-[3-(4-ethenylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C=CC(C=C)=CC=3)C2=C1 CYYGWWYXMYBLCX-UHFFFAOYSA-N 0.000 claims 1
• XFFUWSWPUCKWPB-UHFFFAOYSA-N n-[3-(4-methylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XFFUWSWPUCKWPB-UHFFFAOYSA-N 0.000 claims 1
• LLVRVDQMPWWGBF-UHFFFAOYSA-N n-[3-(4-methylsulfanylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(SC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O LLVRVDQMPWWGBF-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Chemical class 0.000 abstract description 92
• 230000002401 inhibitory effect Effects 0.000 abstract description 13
• 230000001225 therapeutic effect Effects 0.000 abstract description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 197
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 186
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 180
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 162
• 239000007787 solid Substances 0.000 description 158
• 230000002829 reductive effect Effects 0.000 description 138
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
• 239000000243 solution Substances 0.000 description 121
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 111
• 238000004458 analytical method Methods 0.000 description 109
• 238000002844 melting Methods 0.000 description 106
• 230000008018 melting Effects 0.000 description 106
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 104
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 100
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 97
• 239000000047 product Substances 0.000 description 93
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 90
• 229910001868 water Inorganic materials 0.000 description 84
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 81
• 239000003480 eluent Substances 0.000 description 69
• 238000004587 chromatography analysis Methods 0.000 description 68
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 239000000377 silicon dioxide Substances 0.000 description 61
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 56
• 238000000034 method Methods 0.000 description 54
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 52
• 239000007864 aqueous solution Substances 0.000 description 48
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 48
• 235000019341 magnesium sulphate Nutrition 0.000 description 48
• 239000012153 distilled water Substances 0.000 description 44
• 238000001704 evaporation Methods 0.000 description 44
• 230000008020 evaporation Effects 0.000 description 44
• 239000012429 reaction media Substances 0.000 description 44
• 230000000694 effects Effects 0.000 description 43
• 229920006395 saturated elastomer Polymers 0.000 description 41
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 39
• 239000011541 reaction mixture Substances 0.000 description 39
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
• 235000017557 sodium bicarbonate Nutrition 0.000 description 38
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
• 238000009835 boiling Methods 0.000 description 35
• 108010067715 Focal Adhesion Protein-Tyrosine Kinases Proteins 0.000 description 34
• 102000016621 Focal Adhesion Protein-Tyrosine Kinases Human genes 0.000 description 34
• 210000004027 cell Anatomy 0.000 description 34
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 34
• 239000000284 extract Substances 0.000 description 33
• 239000012074 organic phase Substances 0.000 description 33
• 239000002904 solvent Substances 0.000 description 33
• 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 description 32
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 31
• 239000011521 glass Substances 0.000 description 31
• 239000000725 suspension Substances 0.000 description 31
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 28
• 229910052786 argon Inorganic materials 0.000 description 28
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 26
• 239000002245 particle Substances 0.000 description 26
• 239000002585 base Substances 0.000 description 25
• 230000005764 inhibitory process Effects 0.000 description 25
• 239000000843 powder Substances 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 24
• 229910002027 silica gel Inorganic materials 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
• 239000000706 filtrate Substances 0.000 description 23
• 239000003921 oil Substances 0.000 description 23
• 235000019198 oils Nutrition 0.000 description 23
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 22
• 239000000758 substrate Substances 0.000 description 22
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 20
• 238000001914 filtration Methods 0.000 description 20
• NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 19
• 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 description 19
• 238000010992 reflux Methods 0.000 description 19
• 238000004809 thin layer chromatography Methods 0.000 description 19
• 239000000872 buffer Substances 0.000 description 18
• DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 18
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 17
• 239000008346 aqueous phase Substances 0.000 description 17
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 description 16
• 230000006978 adaptation Effects 0.000 description 16
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 description 15
• 229910021529 ammonia Inorganic materials 0.000 description 15
• 238000002360 preparation method Methods 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
• 238000010908 decantation Methods 0.000 description 14
• 239000012442 inert solvent Substances 0.000 description 14
• 125000006239 protecting group Chemical group 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 13
• 150000003839 salts Chemical class 0.000 description 13
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 230000000875 corresponding effect Effects 0.000 description 12
• 239000006071 cream Substances 0.000 description 12
• 239000013078 crystal Substances 0.000 description 12
• IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 12
• MOBJHQPTGMYKCJ-UHFFFAOYSA-N 3-phenyl-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=CC=C1 MOBJHQPTGMYKCJ-UHFFFAOYSA-N 0.000 description 11
• 230000035578 autophosphorylation Effects 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 230000026731 phosphorylation Effects 0.000 description 11
• 238000006366 phosphorylation reaction Methods 0.000 description 11
• 108090000623 proteins and genes Proteins 0.000 description 11
• 238000000746 purification Methods 0.000 description 11
• 239000012047 saturated solution Substances 0.000 description 11
• 102000004190 Enzymes Human genes 0.000 description 10
• 108090000790 Enzymes Proteins 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
• 230000002378 acidificating effect Effects 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 229940088598 enzyme Drugs 0.000 description 10
• 239000011790 ferrous sulphate Substances 0.000 description 10
• 235000003891 ferrous sulphate Nutrition 0.000 description 10
• 238000003818 flash chromatography Methods 0.000 description 10
• 239000001257 hydrogen Substances 0.000 description 10
• 229910052708 sodium Inorganic materials 0.000 description 10
• 239000003643 water by type Substances 0.000 description 10
• 101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 9
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
• 102100037852 Insulin-like growth factor I Human genes 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 230000014509 gene expression Effects 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 108090000765 processed proteins & peptides Proteins 0.000 description 9
• 102000004169 proteins and genes Human genes 0.000 description 9
• 238000005160 1H NMR spectroscopy Methods 0.000 description 8
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• 210000000988 bone and bone Anatomy 0.000 description 8
• 230000006870 function Effects 0.000 description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
• 229910052749 magnesium Inorganic materials 0.000 description 8
• 239000011777 magnesium Substances 0.000 description 8
• XPJTUCSESGEMOI-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonyl chloride Chemical compound CS(=O)(=O)C1=CC=CC=C1S(Cl)(=O)=O XPJTUCSESGEMOI-UHFFFAOYSA-N 0.000 description 7
• HORRIHWEYDDYST-UHFFFAOYSA-N 3-iodo-2h-indazol-5-amine Chemical compound NC1=CC=C2NN=C(I)C2=C1 HORRIHWEYDDYST-UHFFFAOYSA-N 0.000 description 7
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 7
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 239000000539 dimer Substances 0.000 description 7
• 238000001035 drying Methods 0.000 description 7
• 238000000338 in vitro Methods 0.000 description 7
• RDPLOLUNEKBWBR-UHFFFAOYSA-L magnesium;sodium;sulfate Chemical compound [Na+].[Mg+2].[O-]S([O-])(=O)=O RDPLOLUNEKBWBR-UHFFFAOYSA-L 0.000 description 7
• 238000005259 measurement Methods 0.000 description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
• 238000011160 research Methods 0.000 description 7
• 239000011780 sodium chloride Substances 0.000 description 7
• 150000003456 sulfonamides Chemical class 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 7
• 238000005406 washing Methods 0.000 description 7
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
• 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 6
• 102000005720 Glutathione transferase Human genes 0.000 description 6
• 108010070675 Glutathione transferase Proteins 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 6
• 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 6
• 230000004913 activation Effects 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 239000012300 argon atmosphere Substances 0.000 description 6
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• 238000001033 granulometry Methods 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
• 238000011534 incubation Methods 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
• XBTOSRUBOXQWBO-UHFFFAOYSA-N 1h-indazol-5-amine Chemical compound NC1=CC=C2NN=CC2=C1 XBTOSRUBOXQWBO-UHFFFAOYSA-N 0.000 description 5
• GHFKCBWRZWDFKB-UHFFFAOYSA-N 1h-indazole-3,5-diamine Chemical compound C1=C(N)C=C2C(N)=NNC2=C1 GHFKCBWRZWDFKB-UHFFFAOYSA-N 0.000 description 5
• 102100034594 Angiopoietin-1 Human genes 0.000 description 5
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• SVIBPSNFXYUOFT-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 SVIBPSNFXYUOFT-UHFFFAOYSA-N 0.000 description 5
• 230000003213 activating effect Effects 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• 239000007795 chemical reaction product Substances 0.000 description 5
• 230000008878 coupling Effects 0.000 description 5
• 238000010168 coupling process Methods 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 5
• 238000010790 dilution Methods 0.000 description 5
• 239000012895 dilution Substances 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 150000002500 ions Chemical class 0.000 description 5
• 229940043355 kinase inhibitor Drugs 0.000 description 5
• 238000006396 nitration reaction Methods 0.000 description 5
• 150000002894 organic compounds Chemical class 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 238000010647 peptide synthesis reaction Methods 0.000 description 5
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 5
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
• 230000035755 proliferation Effects 0.000 description 5
• 238000006722 reduction reaction Methods 0.000 description 5
• CXGODNRKGDPRKB-UHFFFAOYSA-N tert-butyl 5-amino-3-methylindazole-1-carboxylate Chemical compound C1=C(N)C=C2C(C)=NN(C(=O)OC(C)(C)C)C2=C1 CXGODNRKGDPRKB-UHFFFAOYSA-N 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• 241000701447 unidentified baculovirus Species 0.000 description 5
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 4
• OWZRMMLTVVGUPW-UHFFFAOYSA-N 2-[(3-iodo-5-nitroindazol-1-yl)methoxy]ethyl-trimethylsilane Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(I)C2=C1 OWZRMMLTVVGUPW-UHFFFAOYSA-N 0.000 description 4
• OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 4
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
• 108091007914 CDKs Proteins 0.000 description 4
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 4
• 206010029113 Neovascularisation Diseases 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
• 102000001253 Protein Kinase Human genes 0.000 description 4
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 4
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 230000010933 acylation Effects 0.000 description 4
• 238000005917 acylation reaction Methods 0.000 description 4
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 4
• 239000000908 ammonium hydroxide Substances 0.000 description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 230000012292 cell migration Effects 0.000 description 4
• 230000004663 cell proliferation Effects 0.000 description 4
• 238000002512 chemotherapy Methods 0.000 description 4
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
• GWQVMPWSEVRGPY-UHFFFAOYSA-N europium cryptate Chemical compound [Eu+3].N=1C2=CC=CC=1CN(CC=1N=C(C=CC=1)C=1N=C(C3)C=CC=1)CC(N=1)=CC(C(=O)NCCN)=CC=1C(N=1)=CC(C(=O)NCCN)=CC=1CN3CC1=CC=CC2=N1 GWQVMPWSEVRGPY-UHFFFAOYSA-N 0.000 description 4
• 239000013604 expression vector Substances 0.000 description 4
• 239000000499 gel Substances 0.000 description 4
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 4
• 150000004678 hydrides Chemical class 0.000 description 4
• 150000002430 hydrocarbons Chemical class 0.000 description 4
• 229910052500 inorganic mineral Inorganic materials 0.000 description 4
• 238000004949 mass spectrometry Methods 0.000 description 4
• 235000010755 mineral Nutrition 0.000 description 4
• 239000011707 mineral Substances 0.000 description 4
• 230000037361 pathway Effects 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 108060006633 protein kinase Proteins 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 238000007363 ring formation reaction Methods 0.000 description 4
• 238000000926 separation method Methods 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• KNWHCZXVMBGJRE-UHFFFAOYSA-N 1-(5-hydroxyindazol-1-yl)ethanone Chemical compound OC1=CC=C2N(C(=O)C)N=CC2=C1 KNWHCZXVMBGJRE-UHFFFAOYSA-N 0.000 description 3
• USKRVIRQSQMVDV-UHFFFAOYSA-N 1-(5-phenylmethoxyindazol-1-yl)ethanone Chemical compound C=1C=C2N(C(=O)C)N=CC2=CC=1OCC1=CC=CC=C1 USKRVIRQSQMVDV-UHFFFAOYSA-N 0.000 description 3
• YPOQGIJTFIHXMK-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-nitrophenyl)-1h-indazol-5-yl]benzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C=3C(=CC=CC=3)[N+]([O-])=O)C2=C1 YPOQGIJTFIHXMK-UHFFFAOYSA-N 0.000 description 3
• TVWSCJHLXNWWMQ-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-(2-phenylethyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]benzenesulfonamide Chemical compound C12=CC(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)=CC=C2N(COCC[Si](C)(C)C)N=C1CCC1=CC=CC=C1 TVWSCJHLXNWWMQ-UHFFFAOYSA-N 0.000 description 3
• XMXVCQKFFVBCPM-UHFFFAOYSA-N 2-methylsulfonyl-n-[3-phenylsulfanyl-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]benzenesulfonamide Chemical compound C12=CC(NS(=O)(=O)C=3C(=CC=CC=3)S(C)(=O)=O)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 XMXVCQKFFVBCPM-UHFFFAOYSA-N 0.000 description 3
• NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 3
• WAMFQXZDXAPTPE-UHFFFAOYSA-N 3-(2-phenylethynyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1C#CC1=CC=CC=C1 WAMFQXZDXAPTPE-UHFFFAOYSA-N 0.000 description 3
• BJHMFZLLDMOGMK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=C(Cl)C=C1 BJHMFZLLDMOGMK-UHFFFAOYSA-N 0.000 description 3
• CKJCACIVGSFXTI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-1h-indazol-5-amine Chemical compound C1=CC(OC)=CC=C1C1=NNC2=CC=C(N)C=C12 CKJCACIVGSFXTI-UHFFFAOYSA-N 0.000 description 3
• CXLAMAWMZAQBKK-UHFFFAOYSA-N 3-chloro-2h-indazol-5-amine Chemical compound NC1=CC=C2NN=C(Cl)C2=C1 CXLAMAWMZAQBKK-UHFFFAOYSA-N 0.000 description 3
• UCTRCMYXPOXOSN-UHFFFAOYSA-N 3-iodo-5-nitro-2h-indazole Chemical compound [O-][N+](=O)C1=CC=C2NN=C(I)C2=C1 UCTRCMYXPOXOSN-UHFFFAOYSA-N 0.000 description 3
• FZCSXBWXWJTUAB-UHFFFAOYSA-N 3-phenylsulfanyl-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 FZCSXBWXWJTUAB-UHFFFAOYSA-N 0.000 description 3
• XAFHVHYSJZHBMY-UHFFFAOYSA-N 5-amino-1,2-dihydroindazol-3-one Chemical compound NC1=CC=C2NNC(=O)C2=C1 XAFHVHYSJZHBMY-UHFFFAOYSA-N 0.000 description 3
• KGEYZMRZVKMQBY-UHFFFAOYSA-N 5-amino-1h-indazole-3-carbonitrile Chemical compound NC1=CC=C2NN=C(C#N)C2=C1 KGEYZMRZVKMQBY-UHFFFAOYSA-N 0.000 description 3
• UBVGOYYYXPTKQU-UHFFFAOYSA-N 5-amino-n-phenyl-1h-indazole-3-carboxamide Chemical compound C12=CC(N)=CC=C2NN=C1C(=O)NC1=CC=CC=C1 UBVGOYYYXPTKQU-UHFFFAOYSA-N 0.000 description 3
• FTVFGNHBSCURJP-UHFFFAOYSA-N 5-fluoro-2-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1N FTVFGNHBSCURJP-UHFFFAOYSA-N 0.000 description 3
• XTLYDYMVKAGVIN-UHFFFAOYSA-N 5-nitro-3-phenyl-1h-indazole Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1C1=CC=CC=C1 XTLYDYMVKAGVIN-UHFFFAOYSA-N 0.000 description 3
• OEBYMRZSEMWCPS-UHFFFAOYSA-N 6-methyl-3-phenyl-1h-indazol-5-amine Chemical compound C1=2C=C(N)C(C)=CC=2NN=C1C1=CC=CC=C1 OEBYMRZSEMWCPS-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 206010006187 Breast cancer Diseases 0.000 description 3
• 208000026310 Breast neoplasm Diseases 0.000 description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
• 108010091824 Focal Adhesion Kinase 1 Proteins 0.000 description 3
• 101000924552 Homo sapiens Angiopoietin-1 Proteins 0.000 description 3
• XNONCQOGWPLINT-UHFFFAOYSA-N N-[3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilylethoxymethyl)indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C=1C=C2N(COCC[Si](C)(C)C)N=C(C=3NC4=CC=CC=C4N=3)C2=CC=1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O XNONCQOGWPLINT-UHFFFAOYSA-N 0.000 description 3
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 3
• 108700020796 Oncogene Proteins 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• 108010090804 Streptavidin Proteins 0.000 description 3
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
• 239000012346 acetyl chloride Substances 0.000 description 3
• 230000009471 action Effects 0.000 description 3
• 238000013019 agitation Methods 0.000 description 3
• 238000010640 amide synthesis reaction Methods 0.000 description 3
• 230000002491 angiogenic effect Effects 0.000 description 3
• 230000006907 apoptotic process Effects 0.000 description 3
• 125000005605 benzo group Chemical group 0.000 description 3
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
• 210000000481 breast Anatomy 0.000 description 3
• 239000012267 brine Substances 0.000 description 3
• 244000309464 bull Species 0.000 description 3
• 230000001413 cellular effect Effects 0.000 description 3
• 239000013522 chelant Substances 0.000 description 3
• 210000001072 colon Anatomy 0.000 description 3
• 238000004440 column chromatography Methods 0.000 description 3
• LNZMEOLVTKHUAS-UHFFFAOYSA-N cyclohexane;dichloromethane Chemical compound ClCCl.C1CCCCC1 LNZMEOLVTKHUAS-UHFFFAOYSA-N 0.000 description 3
• 230000001086 cytosolic effect Effects 0.000 description 3
• 238000011161 development Methods 0.000 description 3
• 230000018109 developmental process Effects 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
• 210000002950 fibroblast Anatomy 0.000 description 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
• 108020001507 fusion proteins Proteins 0.000 description 3
• 102000037865 fusion proteins Human genes 0.000 description 3
• 230000012010 growth Effects 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 239000002198 insoluble material Substances 0.000 description 3
• 102000006495 integrins Human genes 0.000 description 3
• 108010044426 integrins Proteins 0.000 description 3
• 125000002346 iodo group Chemical group I* 0.000 description 3
• BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 3
• 229910000359 iron(II) sulfate Inorganic materials 0.000 description 3
• 239000004922 lacquer Substances 0.000 description 3
• 239000007788 liquid Substances 0.000 description 3
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
• 210000004072 lung Anatomy 0.000 description 3
• 230000014759 maintenance of location Effects 0.000 description 3
• 229940095102 methyl benzoate Drugs 0.000 description 3
• OZHTVEXSAHDWFU-UHFFFAOYSA-N n-(3-iodo-2h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2I)C2=C1 OZHTVEXSAHDWFU-UHFFFAOYSA-N 0.000 description 3
• VCAAPKZQXYLMFK-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)benzamide Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1NC(=O)C1=CC=CC=C1 VCAAPKZQXYLMFK-UHFFFAOYSA-N 0.000 description 3
• ZICZTZYYEWXJSV-UHFFFAOYSA-N n-cyclohexyl-5-nitro-1h-indazole-3-carboxamide Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1C(=O)NC1CCCCC1 ZICZTZYYEWXJSV-UHFFFAOYSA-N 0.000 description 3
• 229910052759 nickel Inorganic materials 0.000 description 3
• 230000002018 overexpression Effects 0.000 description 3
• 229910052700 potassium Inorganic materials 0.000 description 3
• 230000005855 radiation Effects 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 3
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
• 108010087686 src-Family Kinases Proteins 0.000 description 3
• 102000009076 src-Family Kinases Human genes 0.000 description 3
• 238000006467 substitution reaction Methods 0.000 description 3
• 230000004083 survival effect Effects 0.000 description 3
• URDVTOKSOBYAHA-UHFFFAOYSA-N tert-butyl 5-amino-3-phenylindazole-1-carboxylate Chemical compound C12=CC(N)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 URDVTOKSOBYAHA-UHFFFAOYSA-N 0.000 description 3
• ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 3
• IIWJLEGVACLVBU-UHFFFAOYSA-N trimethyl-[2-[(5-nitro-3-phenylsulfanylindazol-1-yl)methoxy]ethyl]silane Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(COCC[Si](C)(C)C)N=C1SC1=CC=CC=C1 IIWJLEGVACLVBU-UHFFFAOYSA-N 0.000 description 3
• 210000004881 tumor cell Anatomy 0.000 description 3
• YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
• BKGXBMVBCKGLGG-UHFFFAOYSA-N (1-acetylindazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C=1C=C2N(C(=O)C)N=CC2=CC=1OS(=O)(=O)C1=CC=CC(F)=C1 BKGXBMVBCKGLGG-UHFFFAOYSA-N 0.000 description 2
• LDQLSQRFSNMANA-UHFFFAOYSA-N (2,3,4-trimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1OC LDQLSQRFSNMANA-UHFFFAOYSA-N 0.000 description 2
• TYIKXPOMOYDGCS-UHFFFAOYSA-N (2,3-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1Cl TYIKXPOMOYDGCS-UHFFFAOYSA-N 0.000 description 2
• SZYXKFKWFYUOGZ-UHFFFAOYSA-N (2,3-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1F SZYXKFKWFYUOGZ-UHFFFAOYSA-N 0.000 description 2
• ZYYANAWVBDFAHY-UHFFFAOYSA-N (2,3-dimethylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1C ZYYANAWVBDFAHY-UHFFFAOYSA-N 0.000 description 2
• QNEGDGPAXKYZHZ-UHFFFAOYSA-N (2,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Cl QNEGDGPAXKYZHZ-UHFFFAOYSA-N 0.000 description 2
• QQLRSCZSKQTFGY-UHFFFAOYSA-N (2,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C=C1F QQLRSCZSKQTFGY-UHFFFAOYSA-N 0.000 description 2
• SQTUYFKNCCBFRR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(OC)=C1 SQTUYFKNCCBFRR-UHFFFAOYSA-N 0.000 description 2
• UZKBAGUNURYRQE-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-(4-chlorophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(=O)C=2C=CC(Cl)=CC=2)=C1 UZKBAGUNURYRQE-UHFFFAOYSA-N 0.000 description 2
• RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 2
• DGFCTCGCMKEILT-UHFFFAOYSA-N (2-ethoxyphenyl)boronic acid Chemical compound CCOC1=CC=CC=C1B(O)O DGFCTCGCMKEILT-UHFFFAOYSA-N 0.000 description 2
• QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 2
• ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 2
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
• JKIGHOARKAIPJI-UHFFFAOYSA-N (3,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C(Cl)=C1 JKIGHOARKAIPJI-UHFFFAOYSA-N 0.000 description 2
• RMGYQBHKEWWTOY-UHFFFAOYSA-N (3,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(F)=C1 RMGYQBHKEWWTOY-UHFFFAOYSA-N 0.000 description 2
• RCVDPBFUMYUKPB-UHFFFAOYSA-N (3,4-dimethoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1OC RCVDPBFUMYUKPB-UHFFFAOYSA-N 0.000 description 2
• WQBLCGDZYFKINX-UHFFFAOYSA-N (3,5-dibromophenyl)boronic acid Chemical compound OB(O)C1=CC(Br)=CC(Br)=C1 WQBLCGDZYFKINX-UHFFFAOYSA-N 0.000 description 2
• DKYRKAIKWFHQHM-UHFFFAOYSA-N (3,5-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC(Cl)=C1 DKYRKAIKWFHQHM-UHFFFAOYSA-N 0.000 description 2
• DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 2
• WMMIRQOFEBQWET-UHFFFAOYSA-N (3-butoxycarbonyl-1H-indol-2-yl)boronic acid Chemical compound C1=CC=C2C(C(=O)OCCCC)=C(B(O)O)NC2=C1 WMMIRQOFEBQWET-UHFFFAOYSA-N 0.000 description 2
• WJDZZXIDQYKVDG-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C(Cl)=C1 WJDZZXIDQYKVDG-UHFFFAOYSA-N 0.000 description 2
• SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 2
• WPVBHUUZDFUIJA-UHFFFAOYSA-N (3-fluoro-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1F WPVBHUUZDFUIJA-UHFFFAOYSA-N 0.000 description 2
• DQPDLDQJMUGVGI-UHFFFAOYSA-N (3-fluoro-4-phenylmethoxyphenyl)boronic acid Chemical compound FC1=CC(B(O)O)=CC=C1OCC1=CC=CC=C1 DQPDLDQJMUGVGI-UHFFFAOYSA-N 0.000 description 2
• BWYWXDFYJSIUBE-UHFFFAOYSA-N (3-fluoro-4-phenylphenyl)boronic acid Chemical compound FC1=CC(B(O)O)=CC=C1C1=CC=CC=C1 BWYWXDFYJSIUBE-UHFFFAOYSA-N 0.000 description 2
• WFWQWTPAPNEOFE-UHFFFAOYSA-N (3-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(O)=C1 WFWQWTPAPNEOFE-UHFFFAOYSA-N 0.000 description 2
• BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 2
• QSWLFBMVIGQONC-UHFFFAOYSA-N (3-propan-2-ylphenyl)boronic acid Chemical compound CC(C)C1=CC=CC(B(O)O)=C1 QSWLFBMVIGQONC-UHFFFAOYSA-N 0.000 description 2
• OBQRODBYVNIZJU-UHFFFAOYSA-N (4-acetylphenyl)boronic acid Chemical compound CC(=O)C1=CC=C(B(O)O)C=C1 OBQRODBYVNIZJU-UHFFFAOYSA-N 0.000 description 2
• QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 2
• SRXXSLUUAWHGBZ-UHFFFAOYSA-N (4-chloro-2-methylphenyl)boronic acid Chemical compound CC1=CC(Cl)=CC=C1B(O)O SRXXSLUUAWHGBZ-UHFFFAOYSA-N 0.000 description 2
• QWMJEUJXWVZSAG-UHFFFAOYSA-N (4-ethenylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(C=C)C=C1 QWMJEUJXWVZSAG-UHFFFAOYSA-N 0.000 description 2
• JCIJCHSRVPSOML-UHFFFAOYSA-N (4-fluoro-3-methylphenyl)boronic acid Chemical compound CC1=CC(B(O)O)=CC=C1F JCIJCHSRVPSOML-UHFFFAOYSA-N 0.000 description 2
• PELJYVULHLKXFF-UHFFFAOYSA-N (4-iodophenyl)boronic acid Chemical compound OB(O)C1=CC=C(I)C=C1 PELJYVULHLKXFF-UHFFFAOYSA-N 0.000 description 2
• BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 2
• IVUHTLFKBDDICS-UHFFFAOYSA-N (4-methylsulfanylphenyl)boronic acid Chemical compound CSC1=CC=C(B(O)O)C=C1 IVUHTLFKBDDICS-UHFFFAOYSA-N 0.000 description 2
• DMJHEIDWSIAXCS-UHFFFAOYSA-N (4-phenylmethoxyphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OCC1=CC=CC=C1 DMJHEIDWSIAXCS-UHFFFAOYSA-N 0.000 description 2
• XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
• IAEUFBDMVKQCLU-UHFFFAOYSA-N (4-propan-2-ylphenyl)boronic acid Chemical compound CC(C)C1=CC=C(B(O)O)C=C1 IAEUFBDMVKQCLU-UHFFFAOYSA-N 0.000 description 2
• MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 2
• FMBVAOHFMSQDGT-UHFFFAOYSA-N (5-chloro-2-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(Cl)C=C1B(O)O FMBVAOHFMSQDGT-UHFFFAOYSA-N 0.000 description 2
• JFCLNCVCDFUJPO-UHFFFAOYSA-N (5-chlorothiophen-2-yl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)S1 JFCLNCVCDFUJPO-UHFFFAOYSA-N 0.000 description 2
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
• CMHPUBKZZPSUIQ-UHFFFAOYSA-N 1,3-benzodioxol-5-ylboronic acid Chemical compound OB(O)C1=CC=C2OCOC2=C1 CMHPUBKZZPSUIQ-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• VHADYSUJZAPXOW-UHFFFAOYSA-N 1h-indol-5-ylboronic acid Chemical compound OB(O)C1=CC=C2NC=CC2=C1 VHADYSUJZAPXOW-UHFFFAOYSA-N 0.000 description 2
• BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 2
• YMZVPMQBIGSBOW-UHFFFAOYSA-N 2-methyl-4-phenylmethoxyaniline Chemical compound C1=C(N)C(C)=CC(OCC=2C=CC=CC=2)=C1 YMZVPMQBIGSBOW-UHFFFAOYSA-N 0.000 description 2
• FGJKBCSPHCQGBO-UHFFFAOYSA-N 3-(2-phenylethynyl)-2h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C#CC1=CC=CC=C1 FGJKBCSPHCQGBO-UHFFFAOYSA-N 0.000 description 2
• AGZGTCUSGGVSFV-UHFFFAOYSA-N 3-(4-fluorophenyl)-1h-indazol-5-amine Chemical compound C12=CC(N)=CC=C2NN=C1C1=CC=C(F)C=C1 AGZGTCUSGGVSFV-UHFFFAOYSA-N 0.000 description 2
• WWMGJOLTXIRUQG-UHFFFAOYSA-N 3-n-benzyl-1h-indazole-3,5-diamine Chemical compound C12=CC(N)=CC=C2NN=C1NCC1=CC=CC=C1 WWMGJOLTXIRUQG-UHFFFAOYSA-N 0.000 description 2
• KARXTMOFQRNVKH-UHFFFAOYSA-N 3-n-methyl-1h-indazole-3,5-diamine Chemical compound C1=C(N)C=C2C(NC)=NNC2=C1 KARXTMOFQRNVKH-UHFFFAOYSA-N 0.000 description 2
• DIUCTHUYGZNUJD-UHFFFAOYSA-N 4-fluoro-1-methylsulfonyl-2-nitrobenzene Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1[N+]([O-])=O DIUCTHUYGZNUJD-UHFFFAOYSA-N 0.000 description 2
• URLYIPCFQVDOEZ-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-1h-indazole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 URLYIPCFQVDOEZ-UHFFFAOYSA-N 0.000 description 2
• XXIHMGJTNOUDFH-UHFFFAOYSA-N 5-amino-n-cyclohexyl-1h-indazole-3-carboxamide Chemical compound C12=CC(N)=CC=C2NN=C1C(=O)NC1CCCCC1 XXIHMGJTNOUDFH-UHFFFAOYSA-N 0.000 description 2
• YNAHBAQYMSEIFX-UHFFFAOYSA-N 5-amino-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C(N)C=C2C(C(=O)NC)=NNC2=C1 YNAHBAQYMSEIFX-UHFFFAOYSA-N 0.000 description 2
• GNLPXSBVPWIRBG-UHFFFAOYSA-N 5-fluoro-2-methylsulfonylbenzenesulfonyl chloride Chemical compound CS(=O)(=O)C1=CC=C(F)C=C1S(Cl)(=O)=O GNLPXSBVPWIRBG-UHFFFAOYSA-N 0.000 description 2
• JTZWISIFAPIBCT-UHFFFAOYSA-N 5-nitro-1-(2-trimethylsilylethoxymethyl)indazole-3-carbaldehyde Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(C=O)C2=C1 JTZWISIFAPIBCT-UHFFFAOYSA-N 0.000 description 2
• OXZAZOUXAFCGMY-UHFFFAOYSA-N 5-nitro-1-(2-trimethylsilylethoxymethyl)indazole-3-carboxylic acid Chemical compound [O-][N+](=O)C1=CC=C2N(COCC[Si](C)(C)C)N=C(C(O)=O)C2=C1 OXZAZOUXAFCGMY-UHFFFAOYSA-N 0.000 description 2
• SWZRTDLKPZAFDT-UHFFFAOYSA-N 5-nitro-1h-indazol-3-amine Chemical compound C1=C([N+]([O-])=O)C=C2C(N)=NNC2=C1 SWZRTDLKPZAFDT-UHFFFAOYSA-N 0.000 description 2
• WXTZAAHDBOKXDI-UHFFFAOYSA-N 5-nitro-1h-indazole-3-carbonitrile Chemical compound [O-][N+](=O)C1=CC=C2NN=C(C#N)C2=C1 WXTZAAHDBOKXDI-UHFFFAOYSA-N 0.000 description 2
• MLTOGNYOQHDCAN-UHFFFAOYSA-N 5-nitro-1h-indazole-3-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(C(=O)O)=NNC2=C1 MLTOGNYOQHDCAN-UHFFFAOYSA-N 0.000 description 2
• HMMPHXCOTBASBC-UHFFFAOYSA-N 6-methyl-1h-indazole Chemical compound CC1=CC=C2C=NNC2=C1 HMMPHXCOTBASBC-UHFFFAOYSA-N 0.000 description 2
• PMYDCSGPFKERNG-UHFFFAOYSA-N 6-methyl-3-phenyl-1h-indazole Chemical compound N=1NC2=CC(C)=CC=C2C=1C1=CC=CC=C1 PMYDCSGPFKERNG-UHFFFAOYSA-N 0.000 description 2
• MTWSGQZRZPUEPP-UHFFFAOYSA-N 6-methyl-5-nitro-3-phenyl-1h-indazole Chemical compound C1=2C=C([N+]([O-])=O)C(C)=CC=2NN=C1C1=CC=CC=C1 MTWSGQZRZPUEPP-UHFFFAOYSA-N 0.000 description 2
• 108010048154 Angiopoietin-1 Proteins 0.000 description 2
• 102100034608 Angiopoietin-2 Human genes 0.000 description 2
• 206010003571 Astrocytoma Diseases 0.000 description 2
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
• 102000003903 Cyclin-dependent kinases Human genes 0.000 description 2
• 108090000266 Cyclin-dependent kinases Proteins 0.000 description 2
• UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
• 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 2
• UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
• 229910052693 Europium Inorganic materials 0.000 description 2
• 102000018691 Focal Adhesion Kinase 1 Human genes 0.000 description 2
• 230000004707 G1/S transition Effects 0.000 description 2
• 239000007995 HEPES buffer Substances 0.000 description 2
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 2
• 239000007993 MOPS buffer Substances 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• 229910002651 NO3 Inorganic materials 0.000 description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• 102000001332 SRC Human genes 0.000 description 2
• 108060006706 SRC Proteins 0.000 description 2
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
• 206010039491 Sarcoma Diseases 0.000 description 2
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
• WZPOUEKWKYVQMH-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolo[2,3-b]pyridin-2-yl]boronic acid Chemical compound C1=CN=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 WZPOUEKWKYVQMH-UHFFFAOYSA-N 0.000 description 2
• UWDFWVLAHRQSKK-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(OC(F)(F)F)=C1 UWDFWVLAHRQSKK-UHFFFAOYSA-N 0.000 description 2
• WOAORAPRPVIATR-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=CC(C(F)(F)F)=C1 WOAORAPRPVIATR-UHFFFAOYSA-N 0.000 description 2
• PZRPBPMLSSNFOM-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]boronic acid Chemical compound OCC1=CC=C(B(O)O)C=C1 PZRPBPMLSSNFOM-UHFFFAOYSA-N 0.000 description 2
• HUOFUOCSQCYFPW-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(OC(F)(F)F)C=C1 HUOFUOCSQCYFPW-UHFFFAOYSA-N 0.000 description 2
• ALMFIOZYDASRRC-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1 ALMFIOZYDASRRC-UHFFFAOYSA-N 0.000 description 2
• YQKFJYBRZVNXKQ-UHFFFAOYSA-N [Na].BC#N Chemical compound [Na].BC#N YQKFJYBRZVNXKQ-UHFFFAOYSA-N 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 229940100198 alkylating agent Drugs 0.000 description 2
• 239000002168 alkylating agent Substances 0.000 description 2
• 239000005441 aurora Substances 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
• 150000001556 benzimidazoles Chemical class 0.000 description 2
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
• HEGCWAOVTPVFBJ-UHFFFAOYSA-N benzyl 4-chlorosulfonylpiperidine-1-carboxylate Chemical compound C1CC(S(=O)(=O)Cl)CCN1C(=O)OCC1=CC=CC=C1 HEGCWAOVTPVFBJ-UHFFFAOYSA-N 0.000 description 2
• 125000005620 boronic acid group Chemical class 0.000 description 2
• 239000001110 calcium chloride Substances 0.000 description 2
• 229910001628 calcium chloride Inorganic materials 0.000 description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
• 150000003857 carboxamides Chemical class 0.000 description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
• 230000021164 cell adhesion Effects 0.000 description 2
• 230000022131 cell cycle Effects 0.000 description 2
• 210000003793 centrosome Anatomy 0.000 description 2
• 239000003610 charcoal Substances 0.000 description 2
• 210000000349 chromosome Anatomy 0.000 description 2
• 239000002299 complementary DNA Substances 0.000 description 2
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 2
• 230000002596 correlated effect Effects 0.000 description 2
• WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 2
• 229960000684 cytarabine Drugs 0.000 description 2
• 238000006264 debenzylation reaction Methods 0.000 description 2
• 230000007547 defect Effects 0.000 description 2
• 238000001514 detection method Methods 0.000 description 2
• 238000006193 diazotization reaction Methods 0.000 description 2
• 210000002889 endothelial cell Anatomy 0.000 description 2
• 238000006911 enzymatic reaction Methods 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 2
• UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000012634 fragment Substances 0.000 description 2
• PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 230000004927 fusion Effects 0.000 description 2
• 230000009036 growth inhibition Effects 0.000 description 2
• 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 2
• 230000007062 hydrolysis Effects 0.000 description 2
• 238000006460 hydrolysis reaction Methods 0.000 description 2
• 238000001727 in vivo Methods 0.000 description 2
• 238000010348 incorporation Methods 0.000 description 2
• 230000001939 inductive effect Effects 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 230000003993 interaction Effects 0.000 description 2
• 230000003834 intracellular effect Effects 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 230000026045 iodination Effects 0.000 description 2
• 238000006192 iodination reaction Methods 0.000 description 2
• 150000002496 iodine Chemical class 0.000 description 2
• 229910052742 iron Inorganic materials 0.000 description 2
• 239000012948 isocyanate Substances 0.000 description 2
• 150000002513 isocyanates Chemical class 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
• 238000001819 mass spectrum Methods 0.000 description 2
• VPKDCDLSJZCGKE-UHFFFAOYSA-N methanediimine Chemical compound N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• 230000005012 migration Effects 0.000 description 2
• 238000013508 migration Methods 0.000 description 2
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 2
• DVPBGQDBOJJMSD-UHFFFAOYSA-N n-(5-amino-1h-indazol-3-yl)methanesulfonamide Chemical compound C1=C(N)C=C2C(NS(=O)(=O)C)=NNC2=C1 DVPBGQDBOJJMSD-UHFFFAOYSA-N 0.000 description 2
• PDGFYVAVCLLTNU-UHFFFAOYSA-N n-[3-(4-methoxyphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O PDGFYVAVCLLTNU-UHFFFAOYSA-N 0.000 description 2
• FNIDKQFGLADOPA-UHFFFAOYSA-N n-benzyl-5-nitro-1h-indazol-3-amine Chemical compound C12=CC([N+](=O)[O-])=CC=C2NN=C1NCC1=CC=CC=C1 FNIDKQFGLADOPA-UHFFFAOYSA-N 0.000 description 2
• XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
• UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 2
• 238000005897 peptide coupling reaction Methods 0.000 description 2
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
• 235000021317 phosphate Nutrition 0.000 description 2
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
• 125000003367 polycyclic group Chemical group 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 235000011181 potassium carbonates Nutrition 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
• 230000002285 radioactive effect Effects 0.000 description 2
• 239000000376 reactant Substances 0.000 description 2
• 238000005204 segregation Methods 0.000 description 2
• 238000007086 side reaction Methods 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 229910000104 sodium hydride Inorganic materials 0.000 description 2
• VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
• 229910052938 sodium sulfate Inorganic materials 0.000 description 2
• 235000011152 sodium sulphate Nutrition 0.000 description 2
• 239000011550 stock solution Substances 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000011593 sulfur Substances 0.000 description 2
• NAJCRXIRAAIOAN-UHFFFAOYSA-N tert-butyl 5-nitro-3-phenylindazole-1-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 NAJCRXIRAAIOAN-UHFFFAOYSA-N 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 2
• WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 2
• 230000026683 transduction Effects 0.000 description 2
• 238000010361 transduction Methods 0.000 description 2
• 238000012546 transfer Methods 0.000 description 2
• 238000001665 trituration Methods 0.000 description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
• 229920002554 vinyl polymer Polymers 0.000 description 2
• 238000005303 weighing Methods 0.000 description 2
• BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 description 1
• CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
• NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
• BIIBYWQGRFWQKM-JVVROLKMSA-N (2S)-N-[4-(cyclopropylamino)-3,4-dioxo-1-[(3S)-2-oxopyrrolidin-3-yl]butan-2-yl]-2-[[(E)-3-(2,4-dichlorophenyl)prop-2-enoyl]amino]-4,4-dimethylpentanamide Chemical compound CC(C)(C)C[C@@H](C(NC(C[C@H](CCN1)C1=O)C(C(NC1CC1)=O)=O)=O)NC(/C=C/C(C=CC(Cl)=C1)=C1Cl)=O BIIBYWQGRFWQKM-JVVROLKMSA-N 0.000 description 1
• KDVZJKOYSOFXRV-UHFFFAOYSA-N (3,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1C KDVZJKOYSOFXRV-UHFFFAOYSA-N 0.000 description 1
• QWQBQRYFWNIDOC-UHFFFAOYSA-N (3,5-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC(F)=CC(F)=C1 QWQBQRYFWNIDOC-UHFFFAOYSA-N 0.000 description 1
• AFSSVCNPDKKSRR-UHFFFAOYSA-N (3-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Br)=C1 AFSSVCNPDKKSRR-UHFFFAOYSA-N 0.000 description 1
• QZIFSQFNJOSIOO-UHFFFAOYSA-N (3-carbamoyl-1H-indazol-5-yl) 3,4-dichlorobenzenesulfonate [3-(methylcarbamoyl)-1H-indazol-5-yl] 3,4-dichlorobenzenesulfonate Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)OC=1C=C2C(=NNC2=CC1)C(=O)N.CNC(=O)C1=NNC2=CC=C(C=C12)OS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl QZIFSQFNJOSIOO-UHFFFAOYSA-N 0.000 description 1
• MNSDNWOURMJFFE-UHFFFAOYSA-N (3-carbamoyl-1h-indazol-5-yl) 3-fluorobenzenesulfonate Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1OS(=O)(=O)C1=CC=CC(F)=C1 MNSDNWOURMJFFE-UHFFFAOYSA-N 0.000 description 1
• XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
• LMUASBOUSAMURX-UHFFFAOYSA-N (4-ethylsulfanylphenyl)boronic acid Chemical compound CCSC1=CC=C(B(O)O)C=C1 LMUASBOUSAMURX-UHFFFAOYSA-N 0.000 description 1
• PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 1
• VDUKDQTYMWUSAC-UHFFFAOYSA-N (4-methylsulfonylphenyl)boronic acid Chemical compound CS(=O)(=O)C1=CC=C(B(O)O)C=C1 VDUKDQTYMWUSAC-UHFFFAOYSA-N 0.000 description 1
• FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
• FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 1
• BXVIZHCADXKMER-CMDGGOBGSA-N (e)-3-[5-[(2-methylsulfonylphenyl)sulfonylamino]-2h-indazol-3-yl]prop-2-enoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2\C=C\C(O)=O)C2=C1 BXVIZHCADXKMER-CMDGGOBGSA-N 0.000 description 1
• WIKBZUXHNPONPP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-iodo-2-(trifluoromethyl)propane Chemical compound FC(F)(F)C(I)(C(F)(F)F)C(F)(F)F WIKBZUXHNPONPP-UHFFFAOYSA-N 0.000 description 1
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
• 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
• 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
• 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• FLCVDDQJGBHDTD-UHFFFAOYSA-N 1-indazol-2-ylbenzimidazole Chemical class C1=C2C=CC=CC2=NN1N1C2=CC=CC=C2N=C1 FLCVDDQJGBHDTD-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• HNRSLGUSYMJVKK-UHFFFAOYSA-N 1-nitro-3-phenylindazole Chemical compound C12=CC=CC=C2N([N+](=O)[O-])N=C1C1=CC=CC=C1 HNRSLGUSYMJVKK-UHFFFAOYSA-N 0.000 description 1
• VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
• AZQJQRTZFPAGNV-UHFFFAOYSA-N 1-phenylindazole Chemical compound C12=CC=CC=C2C=NN1C1=CC=CC=C1 AZQJQRTZFPAGNV-UHFFFAOYSA-N 0.000 description 1
• 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 1
• DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 1
• DITBWPUMEUDVLU-UHFFFAOYSA-N 1h-indazole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NNC2=C1 DITBWPUMEUDVLU-UHFFFAOYSA-N 0.000 description 1
• OHFQWNSLYSDVDC-UHFFFAOYSA-N 1h-indazole-5-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C2NN=CC2=C1 OHFQWNSLYSDVDC-UHFFFAOYSA-N 0.000 description 1
• OHNCNPVNTFTJLX-UHFFFAOYSA-N 1h-indazole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2NN=CC2=C1 OHNCNPVNTFTJLX-UHFFFAOYSA-N 0.000 description 1
• USASUEYARBQNBM-UHFFFAOYSA-N 1h-indol-2-ylboronic acid Chemical compound C1=CC=C2NC(B(O)O)=CC2=C1 USASUEYARBQNBM-UHFFFAOYSA-N 0.000 description 1
• ZWVYQZBCSXCUOO-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F ZWVYQZBCSXCUOO-UHFFFAOYSA-N 0.000 description 1
• UOJCTEGNHXRPKO-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenesulfonyl chloride Chemical compound FC1=C(F)C(F)=C(S(Cl)(=O)=O)C(F)=C1F UOJCTEGNHXRPKO-UHFFFAOYSA-N 0.000 description 1
• ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
• SHELADVIRCCTFN-UHFFFAOYSA-N 2,5-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(OC)C(S(Cl)(=O)=O)=C1 SHELADVIRCCTFN-UHFFFAOYSA-N 0.000 description 1
• WGGKQIKICKLWGN-UHFFFAOYSA-N 2,6-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(Cl)=C1S(Cl)(=O)=O WGGKQIKICKLWGN-UHFFFAOYSA-N 0.000 description 1
• QXWAUQMMMIMLTO-UHFFFAOYSA-N 2,6-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(F)=C1S(Cl)(=O)=O QXWAUQMMMIMLTO-UHFFFAOYSA-N 0.000 description 1
• ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 1
• ZBJBBHDHWHEJQB-UHFFFAOYSA-N 2-(3-phenyl-1H-indazol-5-yl)-3-thiophen-2-yl-3H-1,2-oxazole Chemical compound C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)N1OC=CC1C1=CC=CS1 ZBJBBHDHWHEJQB-UHFFFAOYSA-N 0.000 description 1
• HIFGQHGWMTZMOH-UHFFFAOYSA-N 2-(trifluoromethoxy)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F HIFGQHGWMTZMOH-UHFFFAOYSA-N 0.000 description 1
• ZIZGWNOAHUCACM-UHFFFAOYSA-N 2-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1S(Cl)(=O)=O ZIZGWNOAHUCACM-UHFFFAOYSA-N 0.000 description 1
• 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
• HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• MUMNFEPQABVDQS-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O MUMNFEPQABVDQS-UHFFFAOYSA-N 0.000 description 1
• HBZMMTAMDTYYIT-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O HBZMMTAMDTYYIT-UHFFFAOYSA-N 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• WPHUUIODWRNJLO-UHFFFAOYSA-N 2-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1S(Cl)(=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
• CBFORTBWOFFDSO-UHFFFAOYSA-N 2-phenyl-1,3-dihydroindazol-5-amine Chemical compound C1C2=CC(N)=CC=C2NN1C1=CC=CC=C1 CBFORTBWOFFDSO-UHFFFAOYSA-N 0.000 description 1
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
• MJAHNNKQLXJQDX-UHFFFAOYSA-N 3,4,5-trimethoxybenzenesulfonamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(OC)=C1OC MJAHNNKQLXJQDX-UHFFFAOYSA-N 0.000 description 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
• NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
• IIQKIICAOXAXEJ-UHFFFAOYSA-N 3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(F)=CC(S(Cl)(=O)=O)=C1 IIQKIICAOXAXEJ-UHFFFAOYSA-N 0.000 description 1
• ANGMUMISTRUCGF-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1C1=NC2=CC=CC=C2N1 ANGMUMISTRUCGF-UHFFFAOYSA-N 0.000 description 1
• GVPTWTKNUYXCQX-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-1H-indazol-5-ol Chemical compound C1=CC=C2NC(C3=NNC4=CC=C(C=C43)O)=NC2=C1 GVPTWTKNUYXCQX-UHFFFAOYSA-N 0.000 description 1
• GTGDHOQVKFEHIX-UHFFFAOYSA-N 3-(1H-benzimidazol-2-yl)-5-phenylmethoxy-1H-indazole Chemical compound C=1C=C2NN=C(C=3NC4=CC=CC=C4N=3)C2=CC=1OCC1=CC=CC=C1 GTGDHOQVKFEHIX-UHFFFAOYSA-N 0.000 description 1
• GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
• BSXPVGDJQOLKMJ-UHFFFAOYSA-N 3-(2-phenylethyl)-1-(2-trimethylsilylethoxymethyl)indazol-5-amine Chemical compound C12=CC(N)=CC=C2N(COCC[Si](C)(C)C)N=C1CCC1=CC=CC=C1 BSXPVGDJQOLKMJ-UHFFFAOYSA-N 0.000 description 1
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
• ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 1
• AOKHRTSXJINPPJ-UHFFFAOYSA-N 3-bromo-2h-indazol-5-amine Chemical compound C1=C(N)C=CC2=NNC(Br)=C21 AOKHRTSXJINPPJ-UHFFFAOYSA-N 0.000 description 1
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
• QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 1
• QMCITVXMMYQIOC-UHFFFAOYSA-N 3-fluorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(F)=C1 QMCITVXMMYQIOC-UHFFFAOYSA-N 0.000 description 1
• FLSKDLNRMBLSMQ-UHFFFAOYSA-N 3-iodo-5-[(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(N(N=C2I)C(O)=O)C2=C1 FLSKDLNRMBLSMQ-UHFFFAOYSA-N 0.000 description 1
• JJERDAVMCCTTBM-UHFFFAOYSA-N 3-methyl-n-(2-methylsulfonylphenyl)-2h-indazole-5-sulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC=C1S(C)(=O)=O JJERDAVMCCTTBM-UHFFFAOYSA-N 0.000 description 1
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• MWWNNNAOGWPTQY-UHFFFAOYSA-N 3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(S(Cl)(=O)=O)=C1 MWWNNNAOGWPTQY-UHFFFAOYSA-N 0.000 description 1
• MXBKCOLSUUYOHT-UHFFFAOYSA-N 3-phenyl-1h-indazole Chemical compound C1=CC=CC=C1C1=NNC2=CC=CC=C12 MXBKCOLSUUYOHT-UHFFFAOYSA-N 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• IWMABJZZIWFKGH-UHFFFAOYSA-N 3-thiophen-2-yl-1,2-oxazole Chemical compound C1=CSC(C2=NOC=C2)=C1 IWMABJZZIWFKGH-UHFFFAOYSA-N 0.000 description 1
• AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• OBMVMHLMAYMFJV-UHFFFAOYSA-N 4-(trifluoromethoxy)benzenesulfonic acid hydrochloride Chemical compound Cl.OS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 OBMVMHLMAYMFJV-UHFFFAOYSA-N 0.000 description 1
• KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
• GFZWLZQOZGNKDW-UHFFFAOYSA-N 4-fluoro-1-methylsulfanyl-2-nitrobenzene Chemical compound CSC1=CC=C(F)C=C1[N+]([O-])=O GFZWLZQOZGNKDW-UHFFFAOYSA-N 0.000 description 1
• APCIZMQSGOFMTI-UHFFFAOYSA-N 4-fluoro-1-methylsulfinyl-2-nitrobenzene Chemical compound CS(=O)C1=CC=C(F)C=C1[N+]([O-])=O APCIZMQSGOFMTI-UHFFFAOYSA-N 0.000 description 1
• BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 1
• SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical class OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
• DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
• YEZADZMMVHWFIY-UHFFFAOYSA-N 4-tert-butylbenzenesulfonyl chloride Chemical compound CC(C)(C)C1=CC=C(S(Cl)(=O)=O)C=C1 YEZADZMMVHWFIY-UHFFFAOYSA-N 0.000 description 1
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
• AZYKVYXJPVOTQX-UHFFFAOYSA-N 5-(sulfonylamino)-1h-indazole Chemical group O=S(=O)=NC1=CC=C2NN=CC2=C1 AZYKVYXJPVOTQX-UHFFFAOYSA-N 0.000 description 1
• NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 1
• LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 description 1
• ZIFCSVSXHXFOAT-UHFFFAOYSA-N 5-amino-1h-indazole-3-carboxylic acid Chemical compound NC1=CC=C2NN=C(C(O)=O)C2=C1 ZIFCSVSXHXFOAT-UHFFFAOYSA-N 0.000 description 1
• NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
• VGSORMNSPJVGNP-UHFFFAOYSA-N 5-methoxy-1-[(2-methylpropan-2-yl)oxy]pyrrolo[2,3-b]pyridine Chemical compound COC1=CN=C2N(OC(C)(C)C)C=CC2=C1 VGSORMNSPJVGNP-UHFFFAOYSA-N 0.000 description 1
• XGSFRTHYHRTUCC-UHFFFAOYSA-N 5-nitro-1,2-dihydroindazol-3-one Chemical compound [O-][N+](=O)C1=CC=C2NNC(=O)C2=C1 XGSFRTHYHRTUCC-UHFFFAOYSA-N 0.000 description 1
• NQAATCGJMPDXHK-UHFFFAOYSA-N 5-phenylmethoxy-1h-indazole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=NNC2=CC=C1OCC1=CC=CC=C1 NQAATCGJMPDXHK-UHFFFAOYSA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
• STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
• 206010001258 Adenoviral infections Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 108010048036 Angiopoietin-2 Proteins 0.000 description 1
• 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 108010024976 Asparaginase Proteins 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 241000972773 Aulopiformes Species 0.000 description 1
• 102000004000 Aurora Kinase A Human genes 0.000 description 1
• 108010006654 Bleomycin Proteins 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
• GIAXKCIDVHHWTB-UHFFFAOYSA-N C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C GIAXKCIDVHHWTB-UHFFFAOYSA-N 0.000 description 1
• QXUJFTNGMXIJKD-UHFFFAOYSA-N C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F Chemical compound C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F QXUJFTNGMXIJKD-UHFFFAOYSA-N 0.000 description 1
• UJABRNLUKGZTON-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F Chemical compound C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F UJABRNLUKGZTON-UHFFFAOYSA-N 0.000 description 1
• XAHPWPPDVPNOJE-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.OC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl Chemical compound C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.C(#N)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.OC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl XAHPWPPDVPNOJE-UHFFFAOYSA-N 0.000 description 1
• JUPODLBGUGQZAB-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1CCNCC1.C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1CCNCC1 Chemical compound C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1CCNCC1.C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1CCNCC1 JUPODLBGUGQZAB-UHFFFAOYSA-N 0.000 description 1
• AIYIAXOOBCILQD-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C=1C=NC=CC1.C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C=1C=NC=CC1 Chemical compound C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C=1C=NC=CC1.C1(=CC=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C=1C=NC=CC1 AIYIAXOOBCILQD-UHFFFAOYSA-N 0.000 description 1
• FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
• BUBNWPKIAMAETF-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C BUBNWPKIAMAETF-UHFFFAOYSA-N 0.000 description 1
• MPMQYEUNYZOIHB-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl Chemical compound C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.C(C1=CC=CC=C1)(=O)NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl MPMQYEUNYZOIHB-UHFFFAOYSA-N 0.000 description 1
• ALRFOPFVBNNFGG-UHFFFAOYSA-N C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F Chemical compound C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.C1(=CC=CC=C1)NC(=O)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F ALRFOPFVBNNFGG-UHFFFAOYSA-N 0.000 description 1
• KTECESWSDCXYIC-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=CC=C(C=C1)O.C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=CC=C(C=C1)O Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=CC=C(C=C1)O.C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=CC=C(C=C1)O KTECESWSDCXYIC-UHFFFAOYSA-N 0.000 description 1
• NWMLBHQTERXGQD-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C=NNC2=CC1.C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C=NNC2=CC1 Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C=NNC2=CC1.C1(=CC=CC=C1)S(=O)(=O)NC=1C=C2C=NNC2=CC1 NWMLBHQTERXGQD-UHFFFAOYSA-N 0.000 description 1
• 101150012716 CDK1 gene Proteins 0.000 description 1
• IHFFWALUXKUUTC-UHFFFAOYSA-N CS(=O)(=O)C1=C(C=CC=C1)NS(=O)(=O)C=1C=C2C(=NNC2=CC1)C1=CC=CC=C1.C(#N)C1=NNC2=CC=C(C=C12)S(=O)(=O)NC1=C(C=CC=C1)S(=O)(=O)C Chemical compound CS(=O)(=O)C1=C(C=CC=C1)NS(=O)(=O)C=1C=C2C(=NNC2=CC1)C1=CC=CC=C1.C(#N)C1=NNC2=CC=C(C=C12)S(=O)(=O)NC1=C(C=CC=C1)S(=O)(=O)C IHFFWALUXKUUTC-UHFFFAOYSA-N 0.000 description 1
• BSXZBTMDVPBSGB-UHFFFAOYSA-N CS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=COC=C1.O1C=C(C=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound CS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C1=COC=C1.O1C=C(C=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C BSXZBTMDVPBSGB-UHFFFAOYSA-N 0.000 description 1
• FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 1
• CGQYOPISRANNDV-UHFFFAOYSA-N ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C CGQYOPISRANNDV-UHFFFAOYSA-N 0.000 description 1
• DEJCBDOMQHWFDT-UHFFFAOYSA-N ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl Chemical compound ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl DEJCBDOMQHWFDT-UHFFFAOYSA-N 0.000 description 1
• USVMSZHBZQRCAZ-UHFFFAOYSA-N ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F Chemical compound ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F USVMSZHBZQRCAZ-UHFFFAOYSA-N 0.000 description 1
• CKITUUJGMSQLLC-UHFFFAOYSA-N ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.N1N=CC2=CC(=CC=C12)NS(=O)(=O)C1=CC(=CC=C1)F.CS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C(=O)N Chemical compound ClC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.N1N=CC2=CC(=CC=C12)NS(=O)(=O)C1=CC(=CC=C1)F.CS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C(=O)N CKITUUJGMSQLLC-UHFFFAOYSA-N 0.000 description 1
• WEAVZYQAXHRWBL-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)Cl.N1N=CC2=CC(=CC=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.FC=1C=C(C=CC1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C(=O)N Chemical compound ClC=1C=C(C=CC1Cl)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)Cl.N1N=CC2=CC(=CC=C12)NS(=O)(=O)C1=CC(=C(C=C1)Cl)Cl.FC=1C=C(C=CC1)S(=O)(=O)NC=1C=C2C(=NNC2=CC1)C(=O)N WEAVZYQAXHRWBL-UHFFFAOYSA-N 0.000 description 1
• 108091026890 Coding region Proteins 0.000 description 1
• 206010009944 Colon cancer Diseases 0.000 description 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
• 208000035473 Communicable disease Diseases 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
• JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
• 102000003910 Cyclin D Human genes 0.000 description 1
• 108090000259 Cyclin D Proteins 0.000 description 1
• YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 description 1
• CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
• 108090000695 Cytokines Proteins 0.000 description 1
• 102000004127 Cytokines Human genes 0.000 description 1
• 108010092160 Dactinomycin Proteins 0.000 description 1
• 206010012689 Diabetic retinopathy Diseases 0.000 description 1
• LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
• SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
• 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 description 1
• HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
• 229940124783 FAK inhibitor Drugs 0.000 description 1
• IFFNDJVGOADATR-UHFFFAOYSA-N FC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2C=NNC2=CC1.FC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2C=NNC2=CC1 Chemical compound FC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2C=NNC2=CC1.FC=1C=C(C=CC1)NS(=O)(=O)C=1C=C2C=NNC2=CC1 IFFNDJVGOADATR-UHFFFAOYSA-N 0.000 description 1
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
• 102100037813 Focal adhesion kinase 1 Human genes 0.000 description 1
• MPJKWIXIYCLVCU-UHFFFAOYSA-N Folinic acid Natural products NC1=NC2=C(N(C=O)C(CNc3ccc(cc3)C(=O)NC(CCC(=O)O)CC(=O)O)CN2)C(=O)N1 MPJKWIXIYCLVCU-UHFFFAOYSA-N 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 230000010190 G1 phase Effects 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• 239000007818 Grignard reagent Substances 0.000 description 1
• 102100033067 Growth factor receptor-bound protein 2 Human genes 0.000 description 1
• 108091009389 Growth factor receptor-bound protein 2 Proteins 0.000 description 1
• 239000007821 HATU Substances 0.000 description 1
• 208000031886 HIV Infections Diseases 0.000 description 1
• 206010018910 Haemolysis Diseases 0.000 description 1
• 101000924533 Homo sapiens Angiopoietin-2 Proteins 0.000 description 1
• 101000798300 Homo sapiens Aurora kinase A Proteins 0.000 description 1
• 101000878536 Homo sapiens Focal adhesion kinase 1 Proteins 0.000 description 1
• 101001077604 Homo sapiens Insulin receptor substrate 1 Proteins 0.000 description 1
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 description 1
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 description 1
• 108090000144 Human Proteins Proteins 0.000 description 1
• 102000003839 Human Proteins Human genes 0.000 description 1
• 108700012441 IGF2 Proteins 0.000 description 1
• XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
• XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
• 206010061216 Infarction Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102100025087 Insulin receptor substrate 1 Human genes 0.000 description 1
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 101710128836 Large T antigen Proteins 0.000 description 1
• 239000002841 Lewis acid Substances 0.000 description 1
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
• GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
• 241000721701 Lynx Species 0.000 description 1
• 108091054455 MAP kinase family Proteins 0.000 description 1
• 102000043136 MAP kinase family Human genes 0.000 description 1
• 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
• GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
• 206010027452 Metastases to bone Diseases 0.000 description 1
• 206010027458 Metastases to lung Diseases 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 229930192392 Mitomycin Natural products 0.000 description 1
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
• DYQYLQUXODPDCF-UHFFFAOYSA-N N-indazol-1-ylmethanesulfonamide Chemical compound CS(=O)(=O)NN1N=CC2=CC=CC=C12 DYQYLQUXODPDCF-UHFFFAOYSA-N 0.000 description 1
• DKUVWZYZBXIHJG-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F.N1C(=CC2=CC=CC=C12)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F Chemical compound N1C(=CC2=CC=CC=C12)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F.N1C(=CC2=CC=CC=C12)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F DKUVWZYZBXIHJG-UHFFFAOYSA-N 0.000 description 1
• QPJHHLGRSDIHCC-UHFFFAOYSA-N N1C(=NC2=C1C=CC=C2)C2=NNC1=CC=C(C=C21)NS(=O)(=O)C2=C(C=CC=C2)S(=O)(=O)C.N2C(=NC1=C2C=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound N1C(=NC2=C1C=CC=C2)C2=NNC1=CC=C(C=C21)NS(=O)(=O)C2=C(C=CC=C2)S(=O)(=O)C.N2C(=NC1=C2C=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C QPJHHLGRSDIHCC-UHFFFAOYSA-N 0.000 description 1
• FWCQHEJOVWJNNX-UHFFFAOYSA-N NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1Cl)Cl.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1Cl)Cl Chemical compound NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1Cl)Cl.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1Cl)Cl FWCQHEJOVWJNNX-UHFFFAOYSA-N 0.000 description 1
• BEWLRWTWZXMVCK-UHFFFAOYSA-N NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1F)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1F)F Chemical compound NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1F)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1F)F BEWLRWTWZXMVCK-UHFFFAOYSA-N 0.000 description 1
• OQELHHPIYJKLBN-UHFFFAOYSA-N NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC(=C1)F)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC(=C1)F)F Chemical compound NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC(=C1)F)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC(=C1)F)F OQELHHPIYJKLBN-UHFFFAOYSA-N 0.000 description 1
• OSIHNSJHMOWNNK-UHFFFAOYSA-N NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F Chemical compound NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F.NC1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=CC(=CC=C1)F OSIHNSJHMOWNNK-UHFFFAOYSA-N 0.000 description 1
• JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
• 208000008636 Neoplastic Processes Diseases 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 102000007999 Nuclear Proteins Human genes 0.000 description 1
• 108010089610 Nuclear Proteins Proteins 0.000 description 1
• LJAQBFNSSUXPNK-UHFFFAOYSA-N O1C(=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.O1C(=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C Chemical compound O1C(=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C.O1C(=CC=C1)C1=NNC2=CC=C(C=C12)NS(=O)(=O)C1=C(C=CC=C1)S(=O)(=O)C LJAQBFNSSUXPNK-UHFFFAOYSA-N 0.000 description 1
• 102000043276 Oncogene Human genes 0.000 description 1
• 108010058765 Oncogene Protein pp60(v-src) Proteins 0.000 description 1
• 235000019502 Orange oil Nutrition 0.000 description 1
• 229930012538 Paclitaxel Natural products 0.000 description 1
• 102000018546 Paxillin Human genes 0.000 description 1
• ACNHBCIZLNNLRS-UHFFFAOYSA-N Paxilline 1 Natural products N1C2=CC=CC=C2C2=C1C1(C)C3(C)CCC4OC(C(C)(O)C)C(=O)C=C4C3(O)CCC1C2 ACNHBCIZLNNLRS-UHFFFAOYSA-N 0.000 description 1
• 239000004264 Petrolatum Substances 0.000 description 1
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 description 1
• 229920001213 Polysorbate 20 Polymers 0.000 description 1
• HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
• 206010060862 Prostate cancer Diseases 0.000 description 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
• 201000004681 Psoriasis Diseases 0.000 description 1
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
• 108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
• 108050002653 Retinoblastoma protein Proteins 0.000 description 1
• 102100025541 S-acyl fatty acid synthase thioesterase, medium chain Human genes 0.000 description 1
• 102000014400 SH2 domains Human genes 0.000 description 1
• 108050003452 SH2 domains Proteins 0.000 description 1
• 102000000395 SH3 domains Human genes 0.000 description 1
• 108050008861 SH3 domains Proteins 0.000 description 1
• 229940124639 Selective inhibitor Drugs 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 102000013275 Somatomedins Human genes 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
• 108700031954 Tgfb1i1/Leupaxin/TGFB1I1 Proteins 0.000 description 1
• FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
• IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
• 108091023040 Transcription factor Proteins 0.000 description 1
• 102000040945 Transcription factor Human genes 0.000 description 1
• 206010052779 Transplant rejections Diseases 0.000 description 1
• 239000007983 Tris buffer Substances 0.000 description 1
• 102000004243 Tubulin Human genes 0.000 description 1
• 108090000704 Tubulin Proteins 0.000 description 1
• 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
• JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
• 101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 description 1
• GBNJRIQSFJFDII-AATRIKPKSA-N [(e)-2-(4-fluorophenyl)ethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=C(F)C=C1 GBNJRIQSFJFDII-AATRIKPKSA-N 0.000 description 1
• VKIJXFIYBAYHOE-VOTSOKGWSA-N [(e)-2-phenylethenyl]boronic acid Chemical compound OB(O)\C=C\C1=CC=CC=C1 VKIJXFIYBAYHOE-VOTSOKGWSA-N 0.000 description 1
• ZWGMJLNXIVRFRJ-UHFFFAOYSA-N [1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrol-2-yl]boronic acid Chemical compound CC(C)(C)OC(=O)N1C=CC=C1B(O)O ZWGMJLNXIVRFRJ-UHFFFAOYSA-N 0.000 description 1
• IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 1
• BPTABBGLHGBJQR-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BPTABBGLHGBJQR-UHFFFAOYSA-N 0.000 description 1
• RIIPFHVHLXPMHQ-UHFFFAOYSA-N [4-(dimethylamino)phenyl]boronic acid Chemical compound CN(C)C1=CC=C(B(O)O)C=C1 RIIPFHVHLXPMHQ-UHFFFAOYSA-N 0.000 description 1
• PZLVPMBCKHDVKT-UHFFFAOYSA-N [5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-2-yl]boronic acid Chemical compound COC1=CC=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 PZLVPMBCKHDVKT-UHFFFAOYSA-N 0.000 description 1
• KKUSHICTVDIAKS-UHFFFAOYSA-N [5-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolo[2,3-b]pyridin-2-yl]boronic acid Chemical compound COC1=CN=C2N(C(=O)OC(C)(C)C)C(B(O)O)=CC2=C1 KKUSHICTVDIAKS-UHFFFAOYSA-N 0.000 description 1
• PZXAQCDMGOGLKE-UHFFFAOYSA-N [Pt].CN(C)c1nc(nc(n1)N(C)C)N(C)C Chemical class [Pt].CN(C)c1nc(nc(n1)N(C)C)N(C)C PZXAQCDMGOGLKE-UHFFFAOYSA-N 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 1
• 230000001133 acceleration Effects 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 1
• PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
• RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 150000003838 adenosines Chemical class 0.000 description 1
• 230000001464 adherent effect Effects 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
• 230000002411 adverse Effects 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 125000003158 alcohol group Chemical group 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 150000003973 alkyl amines Chemical class 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
• AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• JKOQGQFVAUAYPM-UHFFFAOYSA-N amifostine Chemical compound NCCCNCCSP(O)(O)=O JKOQGQFVAUAYPM-UHFFFAOYSA-N 0.000 description 1
• 229960001097 amifostine Drugs 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 229960001220 amsacrine Drugs 0.000 description 1
• XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
• 230000001548 androgenic effect Effects 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 238000010171 animal model Methods 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 229940045799 anthracyclines and related substance Drugs 0.000 description 1
• 229940121363 anti-inflammatory agent Drugs 0.000 description 1
• 239000002260 anti-inflammatory agent Substances 0.000 description 1
• 229940044684 anti-microtubule agent Drugs 0.000 description 1
• 230000001028 anti-proliverative effect Effects 0.000 description 1
• 230000000692 anti-sense effect Effects 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 239000000074 antisense oligonucleotide Substances 0.000 description 1
• 238000012230 antisense oligonucleotides Methods 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 238000000149 argon plasma sintering Methods 0.000 description 1
• CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
• 239000012298 atmosphere Substances 0.000 description 1
• 229940090047 auto-injector Drugs 0.000 description 1
• 229960002756 azacitidine Drugs 0.000 description 1
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
• OJHAHQJRQIOCFK-UHFFFAOYSA-N azane;chloroform;methanol Chemical compound N.OC.ClC(Cl)Cl OJHAHQJRQIOCFK-UHFFFAOYSA-N 0.000 description 1
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
• VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
• 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
• WBUBEMULWILOJA-UHFFFAOYSA-N benzyl 4-[(3-phenyl-1h-indazol-5-yl)sulfamoyl]piperidine-1-carboxylate Chemical compound C1CC(S(=O)(=O)NC=2C=C3C(C=4C=CC=CC=4)=NNC3=CC=2)CCN1C(=O)OCC1=CC=CC=C1 WBUBEMULWILOJA-UHFFFAOYSA-N 0.000 description 1
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• TUWZZXGAUMSUOB-UHFFFAOYSA-N benzyl piperidine-1-carboxylate Chemical compound C1CCCCN1C(=O)OCC1=CC=CC=C1 TUWZZXGAUMSUOB-UHFFFAOYSA-N 0.000 description 1
• 230000003115 biocidal effect Effects 0.000 description 1
• 238000001574 biopsy Methods 0.000 description 1
• 229960002685 biotin Drugs 0.000 description 1
• 235000020958 biotin Nutrition 0.000 description 1
• 239000011616 biotin Substances 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 229960001561 bleomycin Drugs 0.000 description 1
• OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
• 229910052796 boron Inorganic materials 0.000 description 1
• 210000004556 brain Anatomy 0.000 description 1
• 239000011449 brick Substances 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 230000005587 bubbling Effects 0.000 description 1
• 229960002092 busulfan Drugs 0.000 description 1
• OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 1
• WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
• 210000004900 c-terminal fragment Anatomy 0.000 description 1
• 210000004899 c-terminal region Anatomy 0.000 description 1
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
• 229910000024 caesium carbonate Inorganic materials 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 238000004364 calculation method Methods 0.000 description 1
• 208000001969 capillary hemangioma Diseases 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
• 229960004562 carboplatin Drugs 0.000 description 1
• 229960005243 carmustine Drugs 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
• 230000024245 cell differentiation Effects 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000010261 cell growth Effects 0.000 description 1
• 230000033077 cellular process Effects 0.000 description 1
• 230000005754 cellular signaling Effects 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 150000001793 charged compounds Chemical class 0.000 description 1
• 239000003638 chemical reducing agent Substances 0.000 description 1
• 230000003399 chemotactic effect Effects 0.000 description 1
• 229960004630 chlorambucil Drugs 0.000 description 1
• JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
• ZGNIYAPHJAPRMA-UHFFFAOYSA-N chlorine azide Chemical compound ClN=[N+]=[N-] ZGNIYAPHJAPRMA-UHFFFAOYSA-N 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 230000024321 chromosome segregation Effects 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 208000037976 chronic inflammation Diseases 0.000 description 1
• 230000006020 chronic inflammation Effects 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid Chemical class OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
• 229960004316 cisplatin Drugs 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 239000003245 coal Substances 0.000 description 1
• 229960001338 colchicine Drugs 0.000 description 1
• 208000029742 colonic neoplasm Diseases 0.000 description 1
• LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 description 1
• 239000008139 complexing agent Substances 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000004122 cyclic group Chemical group 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• YRUMDWGUXBZEPE-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1.C1CCCCC1 YRUMDWGUXBZEPE-UHFFFAOYSA-N 0.000 description 1
• MJWVCJUSRGLHFO-UHFFFAOYSA-N cyclohexanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CCCCC1 MJWVCJUSRGLHFO-UHFFFAOYSA-N 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 229960004397 cyclophosphamide Drugs 0.000 description 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
• 229960000640 dactinomycin Drugs 0.000 description 1
• 229960000975 daunorubicin Drugs 0.000 description 1
• STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
• 125000005534 decanoate group Chemical class 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• 230000002950 deficient Effects 0.000 description 1
• 230000001419 dependent effect Effects 0.000 description 1
• 238000000151 deposition Methods 0.000 description 1
• 230000003831 deregulation Effects 0.000 description 1
• 229960000605 dexrazoxane Drugs 0.000 description 1
• 238000010586 diagram Methods 0.000 description 1
• ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
• 235000011180 diphosphates Nutrition 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000010494 dissociation reaction Methods 0.000 description 1
• 230000005593 dissociations Effects 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
• 229960003668 docetaxel Drugs 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229960004679 doxorubicin Drugs 0.000 description 1
• 230000002526 effect on cardiovascular system Effects 0.000 description 1
• 238000010828 elution Methods 0.000 description 1
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
• 230000003511 endothelial effect Effects 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• HKSZLNNOFSGOKW-UHFFFAOYSA-N ent-staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(C)O1 HKSZLNNOFSGOKW-UHFFFAOYSA-N 0.000 description 1
• 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
• 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
• 229960001904 epirubicin Drugs 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 230000001076 estrogenic effect Effects 0.000 description 1
• IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
• DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
• VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
• 229960005420 etoposide Drugs 0.000 description 1
• OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
• 230000007717 exclusion Effects 0.000 description 1
• 238000002474 experimental method Methods 0.000 description 1
• 229960000961 floxuridine Drugs 0.000 description 1
• 229960005304 fludarabine phosphate Drugs 0.000 description 1
• GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 150000005699 fluoropyrimidines Chemical class 0.000 description 1
• 229960002949 fluorouracil Drugs 0.000 description 1
• VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
• 235000008191 folinic acid Nutrition 0.000 description 1
• 239000011672 folinic acid Substances 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000009472 formulation Methods 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
• 229960005277 gemcitabine Drugs 0.000 description 1
• 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
• JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical class OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
• 150000004795 grignard reagents Chemical class 0.000 description 1
• 239000003102 growth factor Substances 0.000 description 1
• 230000008588 hemolysis Effects 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 229940022353 herceptin Drugs 0.000 description 1
• 150000004687 hexahydrates Chemical class 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 239000005556 hormone Substances 0.000 description 1
• 229940088597 hormone Drugs 0.000 description 1
• 102000055590 human KDR Human genes 0.000 description 1
• 102000057090 human PTK2 Human genes 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 239000000852 hydrogen donor Substances 0.000 description 1
• FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• 150000002443 hydroxylamines Chemical class 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 229960000908 idarubicin Drugs 0.000 description 1
• 229960001101 ifosfamide Drugs 0.000 description 1
• HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 230000002055 immunohistochemical effect Effects 0.000 description 1
• 230000001976 improved effect Effects 0.000 description 1
• 230000000415 inactivating effect Effects 0.000 description 1
• 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000007574 infarction Effects 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000007912 intraperitoneal administration Methods 0.000 description 1
• 229960004768 irinotecan Drugs 0.000 description 1
• GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
• OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 150000002540 isothiocyanates Chemical class 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 238000000021 kinase assay Methods 0.000 description 1
• 238000011813 knockout mouse model Methods 0.000 description 1
• 238000002372 labelling Methods 0.000 description 1
• 150000003893 lactate salts Chemical class 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 229960001691 leucovorin Drugs 0.000 description 1
• 150000007517 lewis acids Chemical class 0.000 description 1
• 239000002502 liposome Substances 0.000 description 1
• 238000000622 liquid--liquid extraction Methods 0.000 description 1
• 229910052744 lithium Inorganic materials 0.000 description 1
• 229960002247 lomustine Drugs 0.000 description 1
• 230000005923 long-lasting effect Effects 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• YROQEQPFUCPDCP-UHFFFAOYSA-N losoxantrone Chemical compound OCCNCCN1N=C2C3=CC=CC(O)=C3C(=O)C3=C2C1=CC=C3NCCNCCO YROQEQPFUCPDCP-UHFFFAOYSA-N 0.000 description 1
• 229950008745 losoxantrone Drugs 0.000 description 1
• JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 1
• 208000002780 macular degeneration Diseases 0.000 description 1
• USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• 201000004792 malaria Diseases 0.000 description 1
• 150000002688 maleic acid derivatives Chemical class 0.000 description 1
• 201000010893 malignant breast melanoma Diseases 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 239000011565 manganese chloride Substances 0.000 description 1
• 235000002867 manganese chloride Nutrition 0.000 description 1
• 230000035800 maturation Effects 0.000 description 1
• 230000007246 mechanism Effects 0.000 description 1
• 201000001441 melanoma Diseases 0.000 description 1
• 229960001924 melphalan Drugs 0.000 description 1
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
• 230000037353 metabolic pathway Effects 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052751 metal Inorganic materials 0.000 description 1
• 239000002184 metal Substances 0.000 description 1
• 125000005341 metaphosphate group Chemical group 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229960000485 methotrexate Drugs 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
• XSYSJXLOEFZAJT-UHFFFAOYSA-N methylsulfonylbenzene hydrochloride Chemical compound Cl.S(=O)(=O)(C)C1=CC=CC=C1 XSYSJXLOEFZAJT-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• 230000002297 mitogenic effect Effects 0.000 description 1
• 229960004857 mitomycin Drugs 0.000 description 1
• 230000000394 mitotic effect Effects 0.000 description 1
• 229960001156 mitoxantrone Drugs 0.000 description 1
• KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 210000004165 myocardium Anatomy 0.000 description 1
• QMALYKLUMURRBE-UHFFFAOYSA-N n-(1h-indazol-5-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=C2NN=CC2=C1 QMALYKLUMURRBE-UHFFFAOYSA-N 0.000 description 1
• ALXYQCGNBHORNA-UHFFFAOYSA-N n-(3-fluorophenyl)-3-methyl-2h-indazole-5-sulfonamide Chemical compound C1=C2C(C)=NNC2=CC=C1S(=O)(=O)NC1=CC=CC(F)=C1 ALXYQCGNBHORNA-UHFFFAOYSA-N 0.000 description 1
• BYHVSDPWMTXMEM-UHFFFAOYSA-N n-(5-amino-1h-indazol-3-yl)benzamide Chemical compound C12=CC(N)=CC=C2NN=C1NC(=O)C1=CC=CC=C1 BYHVSDPWMTXMEM-UHFFFAOYSA-N 0.000 description 1
• IURXOVLQTYZZIL-UHFFFAOYSA-N n-(5-nitro-1h-indazol-3-yl)methanesulfonamide Chemical compound C1=C([N+]([O-])=O)C=C2C(NS(=O)(=O)C)=NNC2=C1 IURXOVLQTYZZIL-UHFFFAOYSA-N 0.000 description 1
• QMCBKPYLCOZQBJ-UHFFFAOYSA-N n-[2-[5-[(3-fluorophenyl)sulfonylamino]-1h-indazol-3-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC(F)=C1 QMCBKPYLCOZQBJ-UHFFFAOYSA-N 0.000 description 1
• NRJMKBQRMBXALK-UHFFFAOYSA-N n-[3-(4-tert-butylphenyl)-1h-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C1=C2)=NNC1=CC=C2NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O NRJMKBQRMBXALK-UHFFFAOYSA-N 0.000 description 1
• YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
• RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
• SHNYHNHKJNKNNH-UHFFFAOYSA-N n-methyl-5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O SHNYHNHKJNKNNH-UHFFFAOYSA-N 0.000 description 1
• ARUNSGOCVDIGTM-UHFFFAOYSA-N n-methyl-n-(propyliminomethylideneamino)methanamine;hydrochloride Chemical compound Cl.CCCN=C=NN(C)C ARUNSGOCVDIGTM-UHFFFAOYSA-N 0.000 description 1
• HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
• KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
• DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
• OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
• 230000017066 negative regulation of growth Effects 0.000 description 1
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000001613 neoplastic effect Effects 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• 150000002823 nitrates Chemical class 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 210000004940 nucleus Anatomy 0.000 description 1
• WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000006384 oligomerization reaction Methods 0.000 description 1
• 239000010502 orange oil Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 239000011368 organic material Substances 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• LGRLGKDJPSXDFD-UHFFFAOYSA-N oxadiazole-4-sulfonamide Chemical compound NS(=O)(=O)C1=CON=N1 LGRLGKDJPSXDFD-UHFFFAOYSA-N 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 150000003891 oxalate salts Chemical class 0.000 description 1
• DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
• 229960001756 oxaliplatin Drugs 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 238000012856 packing Methods 0.000 description 1
• 229960001592 paclitaxel Drugs 0.000 description 1
• NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• ACNHBCIZLNNLRS-UBGQALKQSA-N paxilline Chemical compound N1C2=CC=CC=C2C2=C1[C@]1(C)[C@@]3(C)CC[C@@H]4O[C@H](C(C)(O)C)C(=O)C=C4[C@]3(O)CC[C@H]1C2 ACNHBCIZLNNLRS-UBGQALKQSA-N 0.000 description 1
• 239000008188 pellet Substances 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 229960002340 pentostatin Drugs 0.000 description 1
• FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
• 210000003668 pericyte Anatomy 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 229940066842 petrolatum Drugs 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
• 208000017983 photosensitivity disease Diseases 0.000 description 1
• 231100000434 photosensitization Toxicity 0.000 description 1
• 125000005498 phthalate group Chemical class 0.000 description 1
• 210000002826 placenta Anatomy 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 238000006116 polymerization reaction Methods 0.000 description 1
• 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
• 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
• 229940072033 potash Drugs 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 229960004694 prednimustine Drugs 0.000 description 1
• 238000004237 preparative chromatography Methods 0.000 description 1
• CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
• 229960000624 procarbazine Drugs 0.000 description 1
• 229940002612 prodrug Drugs 0.000 description 1
• 239000000651 prodrug Substances 0.000 description 1
• 230000002062 proliferating effect Effects 0.000 description 1
• 230000001737 promoting effect Effects 0.000 description 1
• DROIHSMGGKKIJT-UHFFFAOYSA-N propane-1-sulfonamide Chemical compound CCCS(N)(=O)=O DROIHSMGGKKIJT-UHFFFAOYSA-N 0.000 description 1
• KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• KXJJSKYICDAICD-UHFFFAOYSA-N quinolin-8-ylboronic acid Chemical compound C1=CN=C2C(B(O)O)=CC=CC2=C1 KXJJSKYICDAICD-UHFFFAOYSA-N 0.000 description 1
• JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 238000001959 radiotherapy Methods 0.000 description 1
• 229960004432 raltitrexed Drugs 0.000 description 1
• 230000007115 recruitment Effects 0.000 description 1
• 239000003507 refrigerant Substances 0.000 description 1
• 230000008929 regeneration Effects 0.000 description 1
• 238000011069 regeneration method Methods 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 206010039073 rheumatoid arthritis Diseases 0.000 description 1
• 150000003873 salicylate salts Chemical class 0.000 description 1
• 235000019515 salmon Nutrition 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 229960003440 semustine Drugs 0.000 description 1
• 230000019491 signal transduction Effects 0.000 description 1
• 230000011664 signaling Effects 0.000 description 1
• 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
• AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
• 239000004317 sodium nitrate Substances 0.000 description 1
• 235000010344 sodium nitrate Nutrition 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
• KBAVLSAJSYZNDY-UHFFFAOYSA-M sodium;5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxylate Chemical compound [Na+].CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C([O-])=O)C2=C1 KBAVLSAJSYZNDY-UHFFFAOYSA-M 0.000 description 1
• LKYIPGJOXSVWPX-UHFFFAOYSA-M sodium;thiophene-2-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CS1 LKYIPGJOXSVWPX-UHFFFAOYSA-M 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 238000000638 solvent extraction Methods 0.000 description 1
• OJLGASCOGOIOJR-UHFFFAOYSA-N soyasaponin gammag Natural products CC1=C(O)C(=O)CC(OC2CC(C)(C)CC3C4=CCC5C6(C)CCC(OC7OC(C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(=O)O)C(C)(CO)C6CCC5(C)C4(C)CCC23C)O1 OJLGASCOGOIOJR-UHFFFAOYSA-N 0.000 description 1
• 230000020347 spindle assembly Effects 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• HKSZLNNOFSGOKW-FYTWVXJKSA-N staurosporine Chemical compound C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1[C@H]1C[C@@H](NC)[C@@H](OC)[C@]4(C)O1 HKSZLNNOFSGOKW-FYTWVXJKSA-N 0.000 description 1
• CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
• 210000002784 stomach Anatomy 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 150000003890 succinate salts Chemical class 0.000 description 1
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1
• 230000001629 suppression Effects 0.000 description 1
• FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
• 229960005314 suramin Drugs 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000003826 tablet Substances 0.000 description 1
• 150000003892 tartrate salts Chemical class 0.000 description 1
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
• 229960004964 temozolomide Drugs 0.000 description 1
• NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
• 229960001278 teniposide Drugs 0.000 description 1
• LCGKIFRHQLVSLD-UHFFFAOYSA-N tert-butyl 3-aminoindazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)N=C(N)C2=C1 LCGKIFRHQLVSLD-UHFFFAOYSA-N 0.000 description 1
• WJJRAGPHGJELFV-UHFFFAOYSA-N tert-butyl 3-methyl-5-[(2-methylsulfonylphenyl)sulfonylamino]indazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O WJJRAGPHGJELFV-UHFFFAOYSA-N 0.000 description 1
• KCBGEROLUYJDCR-UHFFFAOYSA-N tert-butyl 5-[(3,4-dichlorophenyl)sulfonylamino]-3-methylindazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KCBGEROLUYJDCR-UHFFFAOYSA-N 0.000 description 1
• YLAJWOMNVOQRCJ-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonylamino]-3-methylindazole-1-carboxylate Chemical compound C1=C2C(C)=NN(C(=O)OC(C)(C)C)C2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 YLAJWOMNVOQRCJ-UHFFFAOYSA-N 0.000 description 1
• YCYIWCBFFKYTKP-UHFFFAOYSA-N tert-butyl 5-[(3-fluorophenyl)sulfonylamino]-3-phenylindazole-1-carboxylate Chemical compound C12=CC(NS(=O)(=O)C=3C=C(F)C=CC=3)=CC=C2N(C(=O)OC(C)(C)C)N=C1C1=CC=CC=C1 YCYIWCBFFKYTKP-UHFFFAOYSA-N 0.000 description 1
• IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
• 239000012414 tert-butyl nitrite Substances 0.000 description 1
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
• JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
• 125000003831 tetrazolyl group Chemical group 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
• 229960001196 thiotepa Drugs 0.000 description 1
• 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 210000001685 thyroid gland Anatomy 0.000 description 1
• 229960003087 tioguanine Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
• 229960000303 topotecan Drugs 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 230000001131 transforming effect Effects 0.000 description 1
• 230000009261 transgenic effect Effects 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 108091008578 transmembrane receptors Proteins 0.000 description 1
• 102000027257 transmembrane receptors Human genes 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 150000008648 triflates Chemical class 0.000 description 1
• 230000001960 triggered effect Effects 0.000 description 1
• NCEKVXVLLYIRBI-UHFFFAOYSA-N trimethyl-[2-[(3-phenylsulfanylindazol-1-yl)methoxy]ethyl]silane Chemical compound C1(=CC=CC=C1)SC1=NN(C2=CC=CC=C12)COCC[Si](C)(C)C NCEKVXVLLYIRBI-UHFFFAOYSA-N 0.000 description 1
• FFJQDVCAIYZKHA-UHFFFAOYSA-N trimethyl-[2-[[5-nitro-3-(2-phenylethynyl)indazol-1-yl]methoxy]ethyl]silane Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(COCC[Si](C)(C)C)N=C1C#CC1=CC=CC=C1 FFJQDVCAIYZKHA-UHFFFAOYSA-N 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 230000005740 tumor formation Effects 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
• 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000005500 uronium group Chemical group 0.000 description 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 239000004066 vascular targeting agent Substances 0.000 description 1
• 229960003048 vinblastine Drugs 0.000 description 1
• JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
• OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
• 229960004528 vincristine Drugs 0.000 description 1
• OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
• UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
• 229960004355 vindesine Drugs 0.000 description 1
• GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
• 229960002066 vinorelbine Drugs 0.000 description 1
• GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1