Facile one-pot synthesis of N-acyl-1H-1,2,3-benzotriazoles from internal and terminal olefinic fatty acids and their antimicrobial screening

J Oleo Sci. 2008;57(8):453-7. doi: 10.5650/jos.57.453.

Abstract

N-acyl-1H-1,2,3-benzotriazoles were prepared in good yields by the reaction of benzotriazole and thionyl chloride with olefinic fatty acids under mild reaction conditions. The new compounds 1-(undec-10-enoyl)-1H-1,2,3-benzotriazole (5a),1-[(Z)-octadec-9-enoyl]-1H-1,2,3-benzotriazole (5b), 1-[(9Z,12R)-12-hydroxyoctadec-9-enoyl]-1H-1,2,3-benzotriazole (5c), 1-[(9R,12Z)-9-hydroxyoctadec-12-enoyl]-1H-1,2,3-benzotriazole (5d) formed were characterized on the basis of elemental analysis and spectral data. All the newly synthesized compounds (5a-5d) were screened for their antimicrobial activity and showed good antifungal activity.

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects*
  • Fatty Acids, Unsaturated / chemistry*
  • Fungi / drug effects*
  • Microbial Sensitivity Tests
  • Structure-Activity Relationship
  • Sulfur Oxides / chemistry*
  • Triazoles / chemical synthesis*
  • Triazoles / pharmacology*

Substances

  • Anti-Infective Agents
  • Fatty Acids, Unsaturated
  • Sulfur Oxides
  • Triazoles
  • thionyl chloride