Design, synthesis, and biological evaluation of platensimycin analogues with varying degrees of molecular complexity

被引：101

作者：

Nicolaou, K. C. ^{[1
,2
,3
]}

Stepan, Antonia F. ^{[1
]}

Lister, Troy ^{[1
]}

Li, Ang ^{[1
]}

Montero, Ana ^{[1
]}

Tria, G. Scott ^{[1
]}

Turner, Craig I. ^{[1
,2
]}

Tang, Yefeng ^{[1
]}

Wang, Jianhua ^{[1
]}

Denton, Ross M. ^{[1
]}

Edmonds, David J. ^{[1
]}

机构：

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

[2] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[3] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 39期

基金：

美国国家卫生研究院; 美国国家科学基金会;

关键词：

D O I：

10.1021/ja8044376

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The molecular design, chemical synthesis, and biological evaluation of two distinct series of platensimycin analogues with varying degrees of complexity are described. The first series of compounds probes the biological importance of the benzoic acid subunit of the molecule, while the second series explores the tetracyclic cage domain. The biological data obtained reveal that, while the substituted benzoic acid domain of platensimycin is a highly conserved structural motif within the active compounds with strict functional group requirements, the cage domain of the molecule can tolerate considerable structural modifications without losing biological action. These findings refine our present understanding of the platensimycin pharmacophore and establish certain structure-activity relationships from which the next generation of designed analogues of this new antibiotic may emerge.

引用

页码：13110 / 13119

页数：10

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