AVE-8062, RPR-258062A, AVE-8062A, CS-39-L-Ser.HCl, AC-7700, -Drug Synthesis Database

【结构式】

【药物名称】AVE-8062, RPR-258062A, AVE-8062A, CS-39-L-Ser.HCl, AC-7700

【化学名称】N-[2-Methoxy-5-[2(Z)-(3,4,5-trimethoxyphenyl)vinyl]phenyl]-L-serinamide hydrochloride
　　　　　　2(S)-Amino-3-hydroxy-N-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]phenyl]propanamide hydrochloride

【CA登记号】181816-48-8 (free base)

【分子式】C₂₁H₂₇ClN₂O₆

【分子量】438.91214

【开发单位】Ajinomoto (Originator), Aventis Pharma (Licensee)

【药理作用】Oncolytic Drugs, Solid Tumors Therapy, Antimitotic Drugs, Microtubule-Stabilizing Agents

合成路线1

Coupling of (Z)-1-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)- ethene (I) with N-Fmoc-O-acetyl-L-serine (II) in the presence of DCC and HOBt provided the corresponding serineamide (III). Further deprotection of Fmoc and acetyl groups with NaOH furnished the title compound.

参考文献中间体

【1】 Hatanaka, T.; Ohsumi, K.; Tsuji, T.; Nihei, Y.; Nakagawa, R.; Ohishi, K. (Ajinomoto Co., Inc.); Stilbene derivs. and pharmaceutical compsns. containing them. CA 2171275; EP 0731085; JP 1996301831; US 5674906 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	18228	2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]aniline; 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenylamine	C₁₈H₂₁NO₄	详情	详情
(II)	25685	(2S)-3-(acetoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]propionic acid	C₂₀H₁₉NO₆	详情	详情
(III)	25686	9H-fluoren-9-ylmethyl (1S)-1-[(isopropenyloxy)methyl]-2-[2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]anilino]-2-oxoethylcarbamate	C₃₉H₄₀N₂O₈	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)