CHEMICAL SYNTHESIS AND BIOLOGICAL EVALUATION OF C-2 TAXOIDS

被引：60

作者：

NICOLAOU, KC ^{[1
]}

RENAUD, J ^{[1
]}

NANTERMET, PG ^{[1
]}

COULADOUROS, EA ^{[1
]}

GUY, RK ^{[1
]}

WRASIDLO, W ^{[1
]}

机构：

[1] UNIV CALIF SAN DIEGO, DEPT CHEM & BIOCHEM, LA JOLLA, CA 92093 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 09期

关键词：

D O I：

10.1021/ja00114a005

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient, general method for the synthesis of 1,2-hydroxy esters by regioselective nucleophilic opening of 1,2-cyclic carbonate systems has been developed. A reliable and practical route giving access to the taxoid carbonate 2 from the readily available 10-deacetylbaccatin III (13) has been established. Nucleophilic opening of the carbonate 2 with a variety of nucleophiles provided a number of novel C-2 Taxols. Water-soluble taxoid onium salts (e.g., 31e, 31n, 32, and 34b) were also synthesized and studied. A selected number of taxoids were subjected to cytotoxicity and tubulin polymerization assays as well as in vivo studies. The results of these studies are reported herein.

引用

页码：2409 / 2420

页数：12

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