Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold

被引：11
|
作者：
Holla, Harish [1 ]
Labaied, Mehdi [2 ]
Ngoc Pham [1 ]
Jenkins, Ian D. [1 ]
Stuart, Kenneth [2 ]
Quinn, Ronald J. [1 ]
机构：
[1] Griffith Univ, Eskitis Inst, Brisbane, Qld 4111, Australia
[2] Seattle BioMed, Seattle, WA 98109 USA
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 16期
基金：
澳大利亚研究理事会;
关键词：
Natural product scaffold; Ene reaction; 1,2-Dioxane; Antitrypanosomal; HAT; MARINE SPONGE; DRUG DISCOVERY; PEROXIDES; CHEMISTRY; PLAKORTIN; OXYGEN; ASSAY;
D O I：
10.1016/j.bmcl.2011.06.059
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A short practical synthesis of a new natural product based scaffold (6), based on antitrypanosomal and antimalarial compounds isolated from different Plakortis species is described. The scaffold contains a peroxide unit that is surprisingly stable to chemical manipulation elsewhere in the molecule, enabling it to be elaborated into a small library of derivatives. It is stable to ozonolysis, reductive work-up with dimethylsulfide and the Wittig reaction with stabilized phosphorus ylides. The scaffold along with its Wittig analogues has displayed low to sub-micro molar (0.2-3.3 mu M) antitrypanosomal activity. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4793 / 4797
页数：5
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