Galarubicin hydrochloride, DA-125
盐酸加柔比星Chemical Name: 14-O-(3-Aminopropionyl)-7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)adriamycinone hydrochloride; (8S,10S)-8-(3-Aminopropionyloxyacetyl)-10-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyloxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione hydrochloride
CAS No. 140637-82-7, 195612-80-7 (free base)
项目整合开发状态: Phase II
项目研究机构: Dong-A (Originator)
合成路线:Coupling of daunomycinone (III) with 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (II),which was obtained from 1,3,4-tri-O-acetyl-derivative (I),was performed by a Koenings-Knorr type of reaction to obtain the daunomycin derivative (IV).Deprotection of (IV) with sodium hydroxide in water gave corresponding derivative (V),which was subsequently treated with bromine in dichloromethane and acetone to afford the bromo derivative (VI).Condensation of (VI) with N-Boc-beta-alanine sodium salt (VII) in acetone/water gave the protected beta-alaninate derivative (VIII),which was finally treated with hydrochloride in ether to obtain DA-125.
📌 参考资料/链接：
参考文献标题:Syntheses and antitumor activities of 7-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)-daunomycinone and adriamycinone
文献作者:Tsuchiya,T.; Takagi,Y.; Oka,K.D.; Umezawa,S.; Takeuchi,T.; Wako,N.; Umezawa,H.
参考来源:J Antibiot 1986,39(11),731-3
📄 详细内容
合成路线:Coupling of daunomycinone (III) with 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (II),which was obtained from 1,3,4-tri-O-acetyl-derivative (I),was performed by a Koenings-Knorr type of reaction to obtain the daunomycin derivative (IV).Deprotection of (IV) with sodium hydroxide in water gave corresponding derivative (V),which was subsequently treated with bromine in dichloromethane and acetone to afford the bromo derivative (VI).Condensation of (VI) with N-Boc-beta-alanine sodium salt (VII) in acetone/water gave the protected beta-alaninate derivative (VIII),which was finally treated with hydrochloride in ether to obtain DA-125.
参考文献标题:DA-125
文献作者:Lee,M.G.; Yang,J.
参考来源:Drugs Fut 1996,21(8),782
合成路线:Coupling of daunomycinone (III) with 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide (II),which was obtained from 1,3,4-tri-O-acetyl-derivative (I),was performed by a Koenings-Knorr type of reaction to obtain the daunomycin derivative (IV).Deprotection of (IV) with sodium hydroxide in water gave corresponding derivative (V),which was subsequently treated with bromine in dichloromethane and acetone to afford the bromo derivative (VI).Condensation of (VI) with N-Boc-beta-alanine sodium salt (VII) in acetone/water gave the protected beta-alaninate derivative (VIII),which was finally treated with hydrochloride in ether to obtain DA-125.
参考文献标题:L-Talopyranoside derivs.and process for the preparation of same
文献作者:Ok,D.K.; Kim,M.S.; Jung,D.Y.(Dong-A Pharmaceutical Co.,Ltd.)
参考来源:US 5374746
产品链接: CAS No. 140637-82-7›› 产品链接: CAS No.195612-80-7››