Catharanthine C16 substituent effects on the biomimetic coupling with vindoline: Preparation and evaluation of a key series of vinblastine analogues

被引：42

作者：

Tam, Annie

Gotoh, Hiroaki

Robertson, William M.

Boger, Dale L. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 22期

基金：

美国国家卫生研究院;

关键词：

Vinblastine; Catharanthine; Vindoline; INTRAMOLECULAR DIELS-ALDER/1,3-DIPOLAR CYCLOADDITION; STEREOCONTROLLED TOTAL-SYNTHESIS; BISINDOLE ALKALOID VINBLASTINE; ASYMMETRIC TOTAL-SYNTHESIS; COMPLEX NATURAL-PRODUCTS; DIELS-ALDER REACTIONS; PLANT-CELL CULTURES; BIOLOGICAL EVALUATION; VINCA-ROSEA; BIOGENETIC APPROACH;

D O I：

10.1016/j.bmcl.2010.09.091

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The examination of the catharanthine C16 substituent effects on the Fe(III)-promoted biomimetic coupling reaction with vindoline is detailed, confirming the importance of the presence of a C16 electron-withdrawing substituent, and establishing an unanticipated unique role (> 10-fold) that the C16 methyl ester plays in the expression of the natural product properties. Thus, replacement of the vinblastine C160 methyl ester with an ethyl ester (10-fold), a cyano group (100-fold), an aldehyde (100-fold), a hydroxymethyl group (1000-fold) or a primary carboxamide (> 1000-fold) led to surprisingly large reductions in cytotoxic activity. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6408 / 6410

页数：3

共 59 条

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