桦木醇、羽扇豆醇和乌苏醇氨基丙氧基衍生物的合成及其抗肿瘤活性

[Synthesis and antitumor activity of betulin, erythrodiol and uvaol aminopropoxy derivatives].

作者信息

Kazakova O B, Giniiatullina G V, Tolstikov G A, Baĭkova I P, Zaprutko L, Apryshko G N

出版信息

Bioorg Khim. 2011 May-Jun;37(3):414-24. doi: 10.1134/s1068162011030101.

DOI:10.1134/s1068162011030101

Abstract

The synthesis of aminopropoxy derivatives of betulin, erythrodiol, uvaol and oleantriol via cyanoethylation of triterpenoids hydroxyl groups and subsequent reduction of cyanoethyl fragments is described. High and specific in vitro antitumor activity (cytotoxicity) of 3beta,28-di-O-[3-(aminopropoxy)]lupa-20(29)-ene and 3beta-O-hydroxy-28-O-[3-(aminopropoxy)]olean-12-ene towards a wide range of human tumor cell lines is discovered. The aminopropoxy group is shown to be a new perspective pharmacophor group for design of anticancer agents on the basis of triterpenoids.

摘要

描述了通过三萜类羟基的氰乙基化以及随后氰乙基片段的还原合成桦木醇、红没药醇、羽扇豆醇和齐墩果三醇的氨基丙氧基衍生物。发现3β,28-二-O-[3-(氨基丙氧基)]羽扇-20(29)-烯和3β-O-羟基-28-O-[3-(氨基丙氧基)]齐墩果-12-烯对多种人类肿瘤细胞系具有高且特异的体外抗肿瘤活性（细胞毒性）。氨基丙氧基被证明是基于三萜类设计抗癌药物的一个新的有前景的药效基团。