Synthesis, characterization and antimicrobial activities of novel silver(I) complexes with coumarin substituted N-heterocyclic carbene ligands

Bioorg Med Chem. 2016 Feb 15;24(4):643-50. doi: 10.1016/j.bmc.2015.12.032. Epub 2015 Dec 18.

Abstract

Eight new coumarin substituted silver(I) N-heterocyclic carbene (NHC) complexes were synthesized by the interaction of the corresponding imidazolium or benzimidazolium chlorides and Ag2O in dichloromethane at room temperature. Structures of these complexes were established on the basis of elemental analysis, (1)H NMR, (13)C NMR, IR and mass spectroscopic techniques. The antimicrobial activities of carbene precursors and silver NHC complexes were tested against standard strains: Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungi Candida albicans and Candida tropicalis. Results showed that all the compounds inhibited the growth of the all bacteria and fungi strains and some complexes performed good activities against different microorganisms. Among all the compounds, the most lipophilic complex bis[1-(4-methylene-6,8-dimethyl-2H-chromen-2-one)-3-(naphthalene-2-ylmethyl)benzimidazol-2-ylidene]silver(I) dichloro argentate (5e) was found out as the most active one.

Keywords: Antibacterial; Antifungal; Carbene; Coumarin; Silver.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects
  • Candida albicans / growth & development
  • Candida tropicalis / drug effects
  • Candida tropicalis / growth & development
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Dose-Response Relationship, Drug
  • Escherichia coli / drug effects
  • Escherichia coli / growth & development
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / pharmacology
  • Ligands
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Methane / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / pharmacology*
  • Pseudomonas aeruginosa / drug effects
  • Pseudomonas aeruginosa / growth & development
  • Silver / chemistry
  • Silver / pharmacology*
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / growth & development
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Coumarins
  • Heterocyclic Compounds
  • Ligands
  • Organometallic Compounds
  • carbene
  • Silver
  • coumarin
  • Methane