Novel benzimidazol-2-ylidene carbene precursors and their silver(I) complexes: Potential antimicrobial agents

Bioorg Med Chem. 2016 Aug 15;24(16):3649-56. doi: 10.1016/j.bmc.2016.06.004. Epub 2016 Jun 3.

Abstract

Novel benzimidazolium salts were synthesized as N-heterocyclic carbene (NHC) precursors, these NHC precursors were metallated with Ag2O in dichloromethane at room temperature to give novel silver(I)-NHC complexes. Structures of these benzimidazolium salts and silver(I)-NHC complexes were characterized on the basis of elemental analysis, (1)H NMR, (13)C NMR, IR and LC-MS spectroscopic techniques. A series of benzimidazolium salts and silver(I)-NHC complexes were tested against standard bacterial strains: Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungal strains: Candida albicans and Candida tropicalis. The results showed that benzimidazolium salts inhibited the growth of all bacteria and fungi strains and all silver(I)-NHC complexes performed good activities against different microorganisms.

Keywords: Benzimidazolium salts; Metallopharmaceuticals in vitro antimicrobial activity; N-Heterocyclic carbene; Silver(I)–NHC complexes.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Candida / drug effects
  • Enterococcus faecalis / drug effects
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests
  • Pseudomonas aeruginosa / drug effects
  • Silver / chemistry*
  • Spectrum Analysis / methods
  • Staphylococcus aureus / drug effects

Substances

  • Anti-Infective Agents
  • Benzimidazoles
  • Silver