Total Synthesis and Biological Activity of Natural Product Urukthapelstatin A

被引：18

作者：

Lin, Chun-Chieh ^{[2
]}

Tantisantisom, Worawan ^{[1
]}

McAlpine, Shelli R. ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Kensington, NSW 2052, Australia

[2] San Diego State Univ, Dept Chem & Biochem, San Diego, CA 92182 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 14期

关键词：

MECHERCHARIMYCES-ASPOROPHORIGENENS YM11-542; CANCER CELL-LINES; CYTOTOXIC SUBSTANCE; CYCLIC PEPTIDE; SANSALVAMIDE; DERIVATIVES; THIAZOLE; OXAZOLE; DESIGN; ASCIDIACYCLAMIDE;

D O I：

10.1021/ol401412v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the first total synthesis of the natural product Urkuthaplestatin A (Ustat A) utilizing a convergent synthetic strategy. The characterization and biological activity match those of the previously published natural product. Interestingly, several intermediates, including the linear and serine cyclized precursors, show a 100-fold decrease in cytotoxicity, with IC50's in the low micromolar range. These data indicate that the rigidity and the consecutive aromatic heterocyclic system are responsible for the biological activity.

引用

页码：3574 / 3577

页数：4

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