3-mercapto-1,2,4-triazoles and N-acylated thiosemicarbazides as metallo-β-lactamase inhibitors

Bioorg Med Chem Lett. 2012 Jan 1;22(1):380-6. doi: 10.1016/j.bmcl.2011.10.116. Epub 2011 Nov 6.

Abstract

The production of β-lactamases is an effective strategy by which pathogenic bacteria can develop resistance against β-lactam antibiotics. While inhibitors of serine-β-lactamases are widely used in combination therapy with β-lactam antibiotics, there are no clinically available inhibitors of metallo-β-lactamases (MBLs), and so there is a need for the development of such inhibitors. This work describes the optimisation of a lead inhibitor previously identified by fragment screening of a compound library. We also report that thiosemicarbazide intermediates in the syntheses of these compounds are also moderately potent inhibitors of the IMP-1 MBL from Pseudomonas aeruginosa. The interactions of these inhibitors with the active site of IMP-1 were examined using in silico methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / pharmacology
  • Catalytic Domain
  • Chemistry, Pharmaceutical / methods*
  • Drug Design
  • Drug Resistance, Bacterial
  • Humans
  • Kinetics
  • Metals / chemistry*
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Models, Molecular
  • Pseudomonas aeruginosa / metabolism
  • Semicarbazides / chemistry*
  • Structure-Activity Relationship
  • Triazoles / chemistry*
  • beta-Lactamase Inhibitors*

Substances

  • Anti-Bacterial Agents
  • Metals
  • Semicarbazides
  • Triazoles
  • beta-Lactamase Inhibitors
  • thiosemicarbazide