Design, synthesis, characterization, antimicrobial evaluation and molecular modeling studies of some dehydroacetic acid-chalcone-1,2,3-triazole hybrids

Bioorg Chem. 2018 Apr:77:236-244. doi: 10.1016/j.bioorg.2018.01.016. Epub 2018 Jan 11.

Abstract

A series of new dehydroacetic acid chalcone-1,2,3-triazole hybrids as potential antimicrobial agents was designed, synthesized and characterized by FTIR, NMR and HRMS spectral techniques. All the synthesized compounds were screened in vitro against four bacterial strains (Staphylococcus epidermidis, Bacillus subtilis, Escherichia coli and Pseudomonas aeruginosa) and two fungal strains (Aspergillus niger and Candida albicans). The antimicrobial results indicated that some of the compounds showed remarkable activities comparable to the standard drugs. Most of the compounds exhibited better efficacy compared to the DHA, which is itself an antimicrobial agent. The synergistic effect in biological activity was observed when DHA, chalcone and 1,2,3-triazole are conjugated. The molecular modeling studies of compound 5j into E. coli topoisomerase II DNA gyrase B were also performed.

Keywords: 1,2,3-triazole; Antimicrobial activity; Chalcone; Dehydroacetic acid; Molecular hybridization.

Publication types

  • Research Support, Non-U.S. Gov't

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*
  • Aspergillus niger / drug effects
  • Bacillus subtilis / drug effects
  • Candida albicans / drug effects
  • Chalcone / chemistry
  • Chalcone / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Escherichia coli / drug effects
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Pseudomonas aeruginosa / drug effects
  • Pyrones / chemistry
  • Pyrones / pharmacology*
  • Staphylococcus epidermidis / drug effects
  • Structure-Activity Relationship
  • Triazoles / chemistry
  • Triazoles / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Pyrones
  • Triazoles
  • dehydroacetic acid
  • Chalcone