Antifungal Activity of Salicylanilides and Their Esters with 4-(Trifluoromethyl)benzoic Acid

Molecules. 2012 Aug 7;17(8):9426-42. doi: 10.3390/molecules17089426.

Abstract

Searching for novel antimicrobial agents still represents a current topic in medicinal chemistry. In this study, the synthesis and analytical data of eighteen salicylanilide esters with 4-(trifluoromethyl)benzoic acid are presented. They were assayed in vitro as potential antimycotic agents against eight fungal strains, along with their parent salicylanilides. The antifungal activity of the presented derivatives was not uniform and moulds showed a higher susceptibility with minimum inhibitory concentrations (MIC) ≥ 0.49 µmol/L than yeasts (MIC ≥ 1.95 µmol/L). However, it was not possible to evaluate a range of 4-(trifluoromethyl)benzoates due to their low solubility. In general, the most active salicylanilide was N-(4-bromophenyl)-4-chloro-2-hydroxybenzamide and among esters, the corresponding 2-(4-bromophenylcarbamoyl)-5-chlorophenyl 4-(trifluoromethyl) benzoate exhibited the lowest MIC of 0.49 µmol/L. However, the esterification of salicylanilides by 4-(trifluoromethyl)benzoic acid did not result unequivocally in a higher antifungal potency.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Absidia / drug effects
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Aspergillus fumigatus / drug effects
  • Benzoates / chemical synthesis
  • Benzoates / pharmacology*
  • Candida / drug effects*
  • Esterification
  • Esters
  • Microbial Sensitivity Tests
  • Salicylanilides / chemical synthesis
  • Salicylanilides / pharmacology*
  • Toluene / analogs & derivatives
  • Toluene / chemistry
  • Trichophyton / drug effects
  • Trichosporon / drug effects

Substances

  • Antifungal Agents
  • Benzoates
  • Esters
  • Salicylanilides
  • Toluene
  • 4-(trifluoromethyl)benzoic acid