Bioorganic & Medicinal Chemistry Letters 2013-02-01

Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: identification of the first inhibitor with anti-mycobacterial activity.

María V Buchieri, Leonardo E Riafrecha, Oscar M Rodríguez, Daniela Vullo, Héctor R Morbidoni, Claudiu T Supuran, Pedro A Colinas

Index: Bioorg. Med. Chem. Lett. 23(3) , 740-3, (2013)

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Abstract

A small series of C-cinnamoyl glycoside containing the phenol moiety was tested for the inhibition of the three Mycobacterium tuberculosis β-carbonic anhydrases (CAs, EC 4.2.1.1) with activities in the low micromolar range detected. The compounds were also tested for the inhibition of growth of M. tuberculosis H(37)Rv strain, leading to the identification of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-4-(3-hydroxyphenyl)but-3-en-2-one (1) as the first carbonic anhydrase inhibitor with anti-tubercular activity.Copyright © 2012 Elsevier Ltd. All rights reserved.