Synthesis of novel indole analogues of mycophenolic acid as potential antineoplastic agents

被引：22

作者：

Lai, G ^{[1
]}

Anderson, WK ^{[1
]}

机构：

[1] SUNY Buffalo, Sch Pharm, Dept Med Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 17期

基金：

美国国家卫生研究院;

关键词：

antitumor compounds; indoles; mycophenolic acid; Claisen rearrangements;

D O I：

10.1016/S0040-4020(00)00177-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The expedient synthesis of three novel indole analogues, 2a-c, of mycophenolic acid is described, which involved as the key steps both the Et2O . BF3 catalyzed amino-Claisen rearrangement of N-allylindoline to 7-allylindoline and the ortho ester Claisen rearrangement of the allylic alcohol 12 to the methyl ester 14. The installation of the substituents at the C-3 position in 2b and 2c was accomplished via Vilsmeier formylation and subsequent oxidation-aminolysis or oxidation-methoxylation. The synthetic approach described possesses general usefulness. The analogue 2b showed significant, reproducible antitumor activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2583 / 2590

页数：8

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