FK-143
1H-吲哚-1-丁酸,3-[3-[[双铊[4-(2-甲基丙基)苯基]氨基]苯甲酰]- 1H-吲哚-1-丁酸,3-[3-[[二[4-(2-甲基丙基)苯基]甲基]氨基]苯甲酰]-,盐酸盐 Chemical Name: 4-[3-[3-[Bis(4-isobutylphenyl)methylamino]benzoyl]indol-1-yl]butyric acid
CAS No. 163136-03-6, 139155-45-6 (monoHCl), 139155-29-6 (monoNa salt)
项目整合开发状态: Phase II
项目研究机构: Fujisawa (Originator)
合成路线:The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III),which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V).The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI),which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII).Finally,this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.
📌 参考资料/链接：
参考文献标题:Indole derivs
文献作者:Okada,S.; Sawada,K.; Kayakiri,N.; Saitoh,Y.; Tanaka,H.; Hashimoto,M.(Fujisawa Pharmaceutical Co.,Ltd.)
参考来源:EP 0458207; JP 1992244061; US 5212320; US 5312829
📄 详细内容
合成路线:The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III),which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V).The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI),which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII).Finally,this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.
参考文献标题:FK-143
文献作者:Mealy,N.; Castar,J.
参考来源:Drugs Fut 1996,21(5),473
合成路线:The Friedel-Crafts condensation of indole (I) with 3-nitrobenzoyl chloride (II) by means of AlCl3 in dichloromethane gives 3-(3-nitrobenzoyl)indole (III),which is allowed to react with ethyl 4-bromobutyrate (IV) by means of K2CO3 in DMF to yield 4-[3-(3-nitrobenzoyl)indol-1-yl]butyric acid ethyl ester (V).The hydrolysis of (V) with NaOH in dioxane/water affords the corresponding butyric acid (VI),which is hydrogenated with H2 over Pd/C in methanol/dioxane yielding 3-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (VII).Finally,this compound is condensed with bis(4-isobutylphenyl)chloromethane (VIII) by means of ethyldiisopropylamine in dichloromethane.
参考文献标题:4-(1-Benzoylindol-3-yl)butyric acids and FK143: Novel nonsteroidal inhibitors of steroid 5alpha-reductase (II)
文献作者:Sawada,K.; Okada,S.; Golden,P.; Kayakiri,N.; Sawada,Y.; Hashimoto,M.; Tanaka,H.
参考来源:Chem Pharm Bull 1999,47(4),481
产品链接: CAS No. 163136-03-6›› 产品链接: CAS No.139155-45-6››