CN102614196B - 苯乙酰氟苯水杨酰胺类化合物在制备抗乳腺癌药物中的应用 - Google Patents
苯乙酰氟苯水杨酰胺类化合物在制备抗乳腺癌药物中的应用 Download PDFInfo
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- CN102614196B CN102614196B CN201210055070.8A CN201210055070A CN102614196B CN 102614196 B CN102614196 B CN 102614196B CN 201210055070 A CN201210055070 A CN 201210055070A CN 102614196 B CN102614196 B CN 102614196B
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- isobutyl
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- 238000002360 preparation method Methods 0.000 title claims abstract description 63
- -1 phenylacetyl fluorobenzene salicylamide compound Chemical class 0.000 title claims abstract description 42
- 239000003814 drug Substances 0.000 title claims abstract description 15
- 229940079593 drug Drugs 0.000 title claims abstract description 8
- 206010006187 Breast cancer Diseases 0.000 title claims description 18
- 208000026310 Breast neoplasm Diseases 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 238000011160 research Methods 0.000 abstract description 2
- 206010008342 Cervix carcinoma Diseases 0.000 abstract 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 abstract 2
- 201000010881 cervical cancer Diseases 0.000 abstract 2
- 238000012216 screening Methods 0.000 abstract 1
- HUHILBMQLXCBHC-UHFFFAOYSA-N fluorobenzene 2-hydroxybenzamide Chemical compound OC1=C(C(=O)N)C=CC=C1.FC=1C=CC=CC1 HUHILBMQLXCBHC-UHFFFAOYSA-N 0.000 description 86
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 80
- 239000000460 chlorine Substances 0.000 description 55
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 54
- 230000001915 proofreading effect Effects 0.000 description 53
- 238000005160 1H NMR spectroscopy Methods 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 18
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 229910052731 fluorine Inorganic materials 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000001263 acyl chlorides Chemical class 0.000 description 11
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- 229960000616 diflunisal Drugs 0.000 description 10
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- 239000011737 fluorine Substances 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 239000012531 culture fluid Substances 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 238000010025 steaming Methods 0.000 description 9
- 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 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 7
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- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- ZAKNRBRFLQSIBK-UHFFFAOYSA-N 1-(2-fluorophenyl)-2-phenylethanone Chemical compound FC1=CC=CC=C1C(=O)CC1=CC=CC=C1 ZAKNRBRFLQSIBK-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 201000008275 breast carcinoma Diseases 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- SIOJFYRPBYGHOO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetyl chloride Chemical compound FC1=CC=C(CC(Cl)=O)C=C1 SIOJFYRPBYGHOO-UHFFFAOYSA-N 0.000 description 3
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- IDPKTHAVUDXTJE-UHFFFAOYSA-N benzene 2-chloroacetyl chloride Chemical class ClCC(=O)Cl.C1=CC=CC=C1 IDPKTHAVUDXTJE-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 3
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 3
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
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- 210000004881 tumor cell Anatomy 0.000 description 3
- GRPFFDFOPCXQEY-UHFFFAOYSA-N 1-(2-fluorophenyl)-2-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1CC(=O)C1=CC=CC=C1F GRPFFDFOPCXQEY-UHFFFAOYSA-N 0.000 description 2
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- DFQMVNAGSCDSNC-UHFFFAOYSA-N ClCC(=O)Cl.CC(C(C)C)C1=CC=CC=C1 Chemical compound ClCC(=O)Cl.CC(C(C)C)C1=CC=CC=C1 DFQMVNAGSCDSNC-UHFFFAOYSA-N 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 206010025482 malaise Diseases 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
- CUXYQKPIPZXPAW-UHFFFAOYSA-N CC(C)Cc1ccc(C(C)C(Oc(ccc(-c(ccc(F)c2)c2F)c2)c2C(Nc2cc(C)ccc2)=O)=O)cc1 Chemical compound CC(C)Cc1ccc(C(C)C(Oc(ccc(-c(ccc(F)c2)c2F)c2)c2C(Nc2cc(C)ccc2)=O)=O)cc1 CUXYQKPIPZXPAW-UHFFFAOYSA-N 0.000 description 1
- SNEQPQKCARNNJM-UHFFFAOYSA-N COc(cc1)ccc1NC(c(cc(cc1)-c(ccc(F)c2)c2F)c1OC(C=O)c(c(Cl)c1)ccc1Cl)=O Chemical compound COc(cc1)ccc1NC(c(cc(cc1)-c(ccc(F)c2)c2F)c1OC(C=O)c(c(Cl)c1)ccc1Cl)=O SNEQPQKCARNNJM-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- RVDHAVYVCBSBJV-UHFFFAOYSA-N [O-][N+](c(cc1)c(C(F)(F)F)cc1NC(c(cc(cc1)-c(ccc(F)c2)c2F)c1OC(Cc(ccc(Cl)c1)c1Cl)=O)=O)=O Chemical compound [O-][N+](c(cc1)c(C(F)(F)F)cc1NC(c(cc(cc1)-c(ccc(F)c2)c2F)c1OC(Cc(ccc(Cl)c1)c1Cl)=O)=O)=O RVDHAVYVCBSBJV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000011938 amidation process Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
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- 244000309466 calf Species 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
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- 238000006482 condensation reaction Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
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- 239000003205 fragrance Substances 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
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- 229940055695 pancreatin Drugs 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Description
化合物 | R | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
I-1 | H | H | F | 式(Q) | H | H | H | H | H |
I-2 | H | H | F | 式(Q) | CH3 | H | H | H | H |
I-3 | H | H | F | 式(Q) | H | CH3 | H | H | H |
I-4 | H | H | F | 式(Q) | H | H | CH3 | H | H |
I-5 | H | H | F | 式(Q) | H | H | F | H | H |
I-6 | H | H | F | 式(Q) | Cl | H | H | H | H |
I-7 | H | H | F | 式(Q) | H | Cl | H | H | H |
I-8 | H | H | F | 式(Q) | H | H | Cl | H | H |
I-9 | H | H | F | 式(Q) | -OCH3 | H | H | H | H |
I-10 | H | H | F | 式(Q) | H | H | -OCH3 | H | H |
I-11 | H | H | F | 式(Q) | F | H | F | H | H |
I-12 | H | H | F | 式(Q) | Cl | H | H | Cl | H |
I-13 | H | H | F | 式(Q) | -NO2 | H | Cl | H | H |
I-14 | H | H | F | 式(Q) | H | CF3 | -NO2 | H | H |
I-15 | H | H | F | 苄基 | / | / | / | / | / |
I-16 | H | H | F | 环己基 | / | / | / | / | / |
I-17 | H | Cl | Cl | 式(Q) | H | H | H | H | H |
I-18 | H | Cl | Cl | 式(Q) | CH3 | H | H | H | H |
I-19 | H | Cl | Cl | 式(Q) | H | CH3 | H | H | H |
I-20 | H | Cl | Cl | 式(Q) | H | H | CH3 | H | H |
I-21 | H | Cl | Cl | 式(Q) | H | H | F | H | H |
I-22 | H | Cl | Cl | 式(Q) | Cl | H | H | H | H |
I-23 | H | Cl | Cl | 式(Q) | H | Cl | H | H | H |
I-24 | H | Cl | Cl | 式(Q) | H | H | Cl | H | H |
I-25 | H | Cl | Cl | 式(Q) | -OCH3 | H | H | H | H |
I-26 | H | Cl | Cl | 式(Q) | H | H | -OCH3 | H | H |
I-27 | H | Cl | Cl | 式(Q) | F | H | F | H | H |
I-28 | H | Cl | Cl | 式(Q) | Cl | H | H | Cl | H |
I-29 | H | Cl | Cl | 式(Q) | -NO2 | H | Cl | H | H |
I-30 | H | Cl | Cl | 式(Q) | H | CF3 | -NO2 | H | H |
I-31 | H | Cl | Cl | 苄基 | / | / | / | / | / |
I-32 | H | Cl | Cl | 环己基 | / | / | / | / | / |
I-33 | CH3 | H | 异丁基 | 式(Q) | H | H | H | H | H |
I-34 | CH3 | H | 异丁基 | 式(Q) | CH3 | H | H | H | H |
I-35 | CH3 | H | 异丁基 | 式(Q) | H | CH3 | H | H | H |
I-36 | CH3 | H | 异丁基 | 式(Q) | H | H | CH3 | H | H |
I-37 | CH3 | H | 异丁基 | 式(Q) | H | H | F | H | H |
I-39 | CH3 | H | 异丁基 | 式(Q) | H | H | Cl | H | H |
I-40 | CH3 | H | 异丁基 | 式(Q) | H | H | -OCH3 | H | H |
I-41 | CH3 | H | 异丁基 | 式(Q) | F | H | F | H | H |
I-42 | CH3 | H | 异丁基 | 式(Q) | Cl | H | H | Cl | H |
实施例 | 化合物 | IC50mg/L | 评价 |
46 | I-1 | 1.25 | 有效 |
47 | I-2 | 0.03 | 显著 |
48 | I-3 | 12.15 | 弱效 |
49 | I-4 | 4.98 | 有效 |
50 | I-5 | 0.38 | 显著 |
51 | I-6 | 2.29 | 有效 |
52 | I-7 | 0.27 | 显著 |
53 | I-8 | 1.25 | 有效 |
54 | I-9 | 9.17 | 有效 |
55 | I-10 | 9.59 | 有效 |
56 | I-11 | 1.09 | 有效 |
57 | I-12 | 0.06 | 显著 |
58 | I-13 | 9.27 | 有效 |
59 | I-14 | 1.42 | 有效 |
60 | I-15 | 7.65 | 有效 |
61 | I-16 | 4.49 | 有效 |
62 | I-17 | 1.63 | 有效 |
63 | I-18 | 7.03 | 有效 |
64 | I-19 | 8.49 | 有效 |
65 | I-20 | 4.54 | 有效 |
66 | I-21 | 0.28 | 显著 |
67 | I-22 | 6.21 | 有效 |
68 | I-23 | 0.22 | 显著 |
69 | I-24 | 0.86 | 显著 |
70 | I-25 | 4.74 | 有效 |
71 | I-26 | 6.78 | 有效 |
72 | I-27 | 5.27 | 有效 |
73 | I-28 | 0.06 | 显著 |
74 | I-29 | 4.47 | 有效 |
75 | I-30 | 2.57 | 有效 |
76 | I-31 | 6.47 | 有效 |
77 | I-32 | 5.74 | 有效 |
78 | I-33 | 8.18 | 有效 |
79 | I-34 | 4.03 | 有效 |
80 | I-35 | 39.12 | 弱效 |
81 | I-36 | 1.51 | 有效 |
82 | I-37 | 1.24 | 有效 |
83 | I-38 | 70.98 | 无效 |
84 | I-39 | 33.85 | 弱效 |
85 | I-40 | 34.86 | 弱效 |
86 | I-41 | 5.75 | 有效 |
87 | I-42 | 44.55 | 弱效 |
88 | 顺铂 | 6.18 | 有效 |
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CN101502523A (zh) * | 2009-03-06 | 2009-08-12 | 浙江工业大学 | 苯甲酰氟苯水杨酰胺类化合物在制备抗肿瘤药物中的应用 |
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CN101502524A (zh) * | 2009-03-13 | 2009-08-12 | 浙江工业大学 | 乙酰氟苯水杨酰胺类化合物在制备抗肿瘤药物中的应用 |
CN101955442A (zh) * | 2010-09-30 | 2011-01-26 | 浙江工业大学 | 一种苯甲酰氟苯水杨酰胺类化合物及应用 |
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CN101502523A (zh) * | 2009-03-06 | 2009-08-12 | 浙江工业大学 | 苯甲酰氟苯水杨酰胺类化合物在制备抗肿瘤药物中的应用 |
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