Elliprabin, Ellipravin, SUN-4599, -Drug Synthesis Database

【结构式】

【药物名称】Elliprabin, Ellipravin, SUN-4599

【化学名称】9-Hydroxy-5,11-dimethyl-2-(3alpha,4beta,5beta-trihydroxytetrahydropyran-2beta-yl)-6H-pyrido[4,3-b]-carbazolium bromide
　　　　　　9-Hydroxy-5,11-dimethyl-2-(alpha-L-arabinopyranosyl)-6H-pyrido[4,3-b]carbazolium bromide
　　　　　　9-Hydroxy-2-(alpha-L-arabinopyranosyl)ellipticinium bromide

【CA登记号】103461-20-7

【分子式】C₂₂H₂₃BrN₂O₅

【分子量】475.34301

【开发单位】Daiichi Suntory Pharma (Originator)

【药理作用】ONCOLYTIC DRUGS

合成路线1

The condensation of 9-acetoxyellipticine (I) with 2,3,4-tri-O-acetyl-beta-L-arabinopyranosyl bromide (II) by means of CdCO3 in refluxing nitromethane gives the corresponding tetraacetoxy derivative (III), which is then deprotected by treatment with dry ammonia in methanol.

参考文献中间体

【1】 Honda, T.; Nakanishi, T. (Suntory Ltd.); Ellipticine derivs.. AU 8545252; EP 0173462; JP 1986037799; JP 1987022794; JP 1987022795; JP 1987030795; US 4698423 .
【2】 Hoshi, A.; Prous, J.; Castaner, J.; ELLIPRAVIN. Drugs Fut 1989, 14, 2, 116.
【3】 Honda, T.; Kato, M.; Inoue, M.; Shimamoto, T.; Shima, K.; Nakanishi, T.; Yoshida, T.; Noguchi, T.; Synthesis and antitumor activity of quaternary ellipticine glycosides, a series of novel and highly active antitumor agents. J Med Chem 1988, 31, 7, 1295-305.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	20352	5,11-dimethyl-6H-pyrido[4,3-b]carbazol-9-yl acetate	C₁₉H₁₆N₂O₂	详情	详情
(II)	20353	(2S,3R,4S,5S)-3,5-bis(acetoxy)-2-bromotetrahydro-2H-pyran-4-yl acetate	C₁₁H₁₅BrO₇	详情	详情
(III)	20354	9-(acetoxy)-5,11-dimethyl-2-[(2R,3R,4S,5S)-3,4,5-tris(acetoxy)tetrahydro-2H-pyran-2-yl]-6H-pyrido[4,3-b]carbazol-2-ium bromide	C₃₀H₃₁BrN₂O₉	详情	详情

Extended Information