Synthesis and biological evaluation of cyclopropyl analogues of fosmidomycin as potent Plasmodium falciparum growth inhibitors

被引:56
|
作者
Devreux, V
Wiesner, J
Goeman, JL
Van der Eycken, J
Jomaa, H
Van Calenbergh, S
机构
[1] Univ Ghent, Fac Sci, Dept Organ Chem, Organ & Bioorgan Chem Lab, B-9000 Ghent, Belgium
[2] Univ Klinikum Giessen, Inst Clin Chem & Pathobiol, D-35392 Giessen, Germany
[3] Univ Klinikum Marburg, Inst Clin Chem & Pathobiol, D-35392 Giessen, Germany
关键词
D O I
10.1021/jm051177c
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of fosmidomycin analogues featuring restricted conformational mobility has been synthesized and evaluated as inhibitors of 1-deoxy-D-xylulose 5-phosphate (DOXP) reductoisomerase and as growth inhibitors of P. falciparum. The enantiomerically pure trans-cyclopropyl N-acetyl analogue 3b showed comparable inhibitory activity as fosmidomycin toward E. coli DOXP reductoisomerase and proved equally active when tested in vitro for P. falciparum growth inhibition. Conversely, the alpha-phenyl cis-cyclopropyl analogue 4 showed virtually no inhibition of the enzyme.
引用
收藏
页码:2656 / 2660
页数:5
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