Clear Search sequence regions

Sizes of these terms reflect their relevance to your search.

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.


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

Expand section icon Mesh Tags

Expand section icon Substances

PMID: 21256013

View Full Text