AVE-8063A, CS-39.HCl, AC-7739, -Drug Synthesis Database

【结构式】

【药物名称】AVE-8063A, CS-39.HCl, AC-7739

【化学名称】3-Amino-3',4,4',5'-tetramethoxy-cis-stilbene hydrochloride
　　　　　　2-Methoxy-5-[2(Z)-(3,4,5-trimethoxyphenyl)vinyl]phenylamine hydrochloride

【CA登记号】

【分子式】C₁₈H₂₂ClNO₄

【分子量】351.83334

【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

Wittig reaction of 3,4,5-trimethoxybenzyl phosphonium bromide (I) with benzaldehyde (II) in the presence of NaH in toluene yielded a 1:1 mixture of E (III) and Z (IV) stilbenes, from which the Z isomer was separated by crystallization from EtOAc and then from EtOH. Then, nitro group of (IV) was reduced with Zn in AcOH at room temperature to give anilino compound (V), which was converted to the hydrochloride salt with HCl in dioxane-methylene chloride.

参考文献中间体

【1】 Suga, Y.; Ohsumi, K.; Fukuda, Y.; Nihei, Y.; Hatanaka, T.; Tsuji, T.; Nakagawa, R.; Morrinaga, Y.; Ohishi, K.; Akiyama, Y.; Novel combretastatin analogue effective against murine solid tumors: Design and structure-activity relationships. J Med Chem 1998, 41, 16, 3022.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	18224	triphenyl(3,4,5-trimethoxybenzyl)phosphorane; 2,3-dimethoxy-5-[(triphenylphosphoranyl)methyl]phenyl methyl ether		C₂₈H₂₉O₃P	详情	详情
(II)	18225	4-METHOXY-3-NITROBENZALDEHYDE	31680-08-7	C₈H₇NO₄	详情	详情
(III)	18226	2,3-dimethoxy-5-[(E)-2-(4-methoxy-3-nitrophenyl)ethenyl]phenyl methyl ether; 1,2,3-trimethoxy-5-[(E)-2-(4-methoxy-3-nitrophenyl)ethenyl]benzene		C₁₈H₁₉NO₆	详情	详情
(IV)	28720	2,3-dimethoxy-5-[(Z)-2-(4-methoxy-3-nitrophenyl)ethenyl]phenyl methyl ether; 1,2,3-trimethoxy-5-[(Z)-2-(4-methoxy-3-nitrophenyl)ethenyl]benzene		C₁₈H₁₉NO₆	详情	详情
(V)	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

Extended Information

Drug NewChemical Entity Original Patent(1)