Antimycobacterial activity of salicylanilide benzenesulfonates

Molecules. 2012 Jan 5;17(1):492-503. doi: 10.3390/molecules17010492.

Abstract

A series of eighteen novel esters of salicylanilides with benzenesulfonic acid were designed, synthesized and characterized by IR, ¹H-NMR and ¹³C-NMR. They were evaluated in vitro as potential antimycobacterial agents towards Mycobacterium tuberculosis, Mycobacterium avium and two strains of Mycobacterium kansasii. In general, the minimum inhibitory concentrations range from 1 to 500 µmol/L. The most active compound against M. tuberculosis was 4-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)-phenyl benzenesulfonate, with MIC of 1 µmol/L and towards M. kansasii its isomer 5-chloro-2-(4-(trifluoromethyl)phenylcarbamoyl)phenyl benzenesulfonate (MIC of 2-4 µmol/L). M. avium was the less susceptible strain. However, generally, salicylanilide benzenesulfonates did not surpass the activity of other salicylanilide esters with carboxylic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Benzenesulfonates / chemical synthesis
  • Benzenesulfonates / chemistry
  • Benzenesulfonates / pharmacology*
  • Drug Design
  • Esterification
  • Esters / chemical synthesis
  • Esters / chemistry
  • Esters / pharmacology*
  • Hydrophobic and Hydrophilic Interactions
  • Microbial Sensitivity Tests
  • Mycobacterium / drug effects*
  • Salicylanilides / chemical synthesis
  • Salicylanilides / chemistry
  • Salicylanilides / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Benzenesulfonates
  • Esters
  • Salicylanilides