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

Bioorg Med Chem Lett. 2013 Feb 1;23(3):740-3. doi: 10.1016/j.bmcl.2012.11.085. Epub 2012 Dec 1.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Carbonic Anhydrase Inhibitors / chemical synthesis*
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Cinnamates / chemistry
  • Glucosides / chemical synthesis*
  • Glucosides / chemistry
  • Glucosides / pharmacology*
  • Glycosides / chemistry*
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Structure-Activity Relationship

Substances

  • 1-(2',3',4',6'-tetra-O-acetylglucopyranosyl)-4-(3-hydroxyphenyl)but-3-en-2-one
  • Antitubercular Agents
  • Carbonic Anhydrase Inhibitors
  • Cinnamates
  • Glucosides
  • Glycosides
  • cinnamoyl chloride