Synthesis and antimicrobial evaluation of ester-linked 1,4-disubstituted 1,2,3-triazoles with a furyl/thienyl moiety

Mol Divers. 2017 Feb;21(1):137-145. doi: 10.1007/s11030-016-9710-y. Epub 2016 Nov 29.

Abstract

Twenty ester-linked 1,4-disubstituted 1,2,3-triazoles having a furyl/thienyl moiety have been synthesized from heteroaryl prop-2-yn-1-yl carboxylate and aromatic azides via a Cu(I) catalyzed 1,3-dipolar cycloaddition. All the synthesized compounds were characterized by FTIR, [Formula: see text]H NMR, [Formula: see text]C NMR spectroscopy and HRMS. Synthesized triazoles were tested in vitro for antimicrobial evaluation against Gram-negative bacteria-Escherichia coli, Enterobacter aerogenes and Klebsiella pneumoniae; Gram-positive bacteria-Staphylococcus aureus and two fungal strains-Candida albicans and Aspergillus niger, reflecting moderate to good activity. The structure of compound 6f was also confirmed by X-ray crystallography (CCDC 1469326).

Keywords: Antibacterial activity; Antifungal activity; Click chemistry; Disubstituted 1,2,3-triazoles; Synthesis.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / metabolism
  • Anti-Infective Agents / pharmacology*
  • Aspergillus niger / drug effects
  • Candida albicans / drug effects
  • Catalytic Domain
  • Chemistry Techniques, Synthetic
  • DNA Gyrase / chemistry
  • DNA Gyrase / metabolism
  • Esters / chemistry*
  • Furans / chemistry*
  • Gram-Negative Bacteria / drug effects
  • Molecular Docking Simulation
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / metabolism
  • Triazoles / pharmacology*

Substances

  • Anti-Infective Agents
  • Esters
  • Furans
  • Triazoles
  • DNA Gyrase
  • furan