Developments of isoCombretastatin A-4 derivatives as highly cytotoxic agents

被引：40

作者：

Hamze, Abdallah ^{[1
]}

Alami, Mouad ^{[1
]}

Provot, Olivier ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, BioCIS, F-92290 Chatenay Malabry, France

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2020年 / 190卷

关键词：

Combretastatin A-4; isoCombretastatin A-4; Heterocycles; Cytotoxicity; Tubulin; Cancer; BIOLOGICAL EVALUATION; COMBRETASTATIN A-4; TUBULIN-POLYMERIZATION; ANTINEOPLASTIC AGENTS; ANTICANCER PROPERTIES; N-TOSYLHYDRAZONES; VERSATILE ACCESS; COLCHICINE SITE; COLON-CANCER; CELL-GROWTH;

D O I：

10.1016/j.ejmech.2020.112110

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Combretastatin A-4 (CA-4) is a natural anti-cancer agent isolated in 1989 from the African willow tree, Combretum caffrum. Due to its chemical simplicity, this (Z)-stilbene has been the subject of many structural modifications mainly to improve its chemical and metabolic stability. Beside a large number of synthetic analogues, isoCombretastatin A-4 (isoCA-4), has proved to be a solution of choice since this non-natural isomer of CA-4 is stable, easier to synthesize and has equivalent antitumor properties as CA-4. In this review, we will present the structure-activity relationships (SARs) around isoCA-4 since its discovery in 2007. In a first part, we will describe some alternatives to replace the phenol B-ring of isoCA-4, then we will focus on the variations made on the 1,1-ethylene double bond and then, we will evocate very recent exiting results concerning the possible replacements of the 3,4,5-trimethoxyphenyl A-ring of isoCA-4 by suitable heterocycles. (C) 2020 Elsevier Masson SAS. All rights reserved.

引用

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