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The electrophilic reactivity of the bioactive marine sponge natural product halenaquinone has been investigated by reaction with the biomimetic nucleophiles N-acetyl-L-cysteine and N(α)-acetyl-L-lysine. While cysteine reacted at the vacant quinone positions C-14 and C-15, lysine was found to react preferentially at the keto-furan position C-1. A small library of analogues was prepared by reaction of halenaquinone with primary amines, and evaluated against a range of biological targets including phospholipase A(2), farnesyltransferases (FTases) and Plasmodium falciparum. Geranylamine analogue 11 exhibited the most potent activity towards FTases (IC(50) 0.017-0.031 μM) and malaria (IC(50) 0.53-0.62 μM). Copyright © 2010 Elsevier Ltd. All rights reserved.

Citation

Jiayi Wang, Marie-Lise Bourguet-Kondracki, Arlette Longeon, Joëlle Dubois, Alexis Valentin, Brent R Copp. Chemical and biological explorations of the electrophilic reactivity of the bioactive marine natural product halenaquinone with biomimetic nucleophiles. Bioorganic & medicinal chemistry letters. 2011 Feb 15;21(4):1261-4

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PMID: 21256013

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