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

Cátedra de Microbiología, Virología y Parasitología, Facultad de Ciencias Médicas, Universidad Nacional de Rosario, Santa Fe 3100, 2000 Rosario, Argentina.

Bioorganic & medicinal chemistry letters 2013 Feb 1

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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.

Citation

María V Buchieri, Leonardo E Riafrecha, Oscar M Rodríguez, Daniela Vullo, Héctor R Morbidoni, Claudiu T Supuran, Pedro A Colinas. Inhibition of the β-carbonic anhydrases from Mycobacterium tuberculosis with C-cinnamoyl glycosides: identification of the first inhibitor with anti-mycobacterial activity. Bioorganic & medicinal chemistry letters. 2013 Feb 1;23(3):740-3