Design and synthesis of new N-(5-trifluoromethyl)-1H-1,2,4-triazol-3-yl benzenesulfonamides as possible antimalarial prototypes

Molecules. 2011 Sep 20;16(9):8083-97. doi: 10.3390/molecules16098083.

Abstract

A rational approach was used to synthesize a new set of 15 1H-1,2,4-triazol-3-yl benzenesulfonamide derivatives with the aim of developing new antimalarial lead compounds. These derivatives were prepared in yields between 50% and 62%, and their structures were elucidated using IR, ¹H-, ¹³C-, ¹⁹F-NMR, MS and elemental analysis. A docking study based on sulfonamides previously used against malaria identified trifluoromethyl-substituted derivatives to be the best lead compounds for new antimalarial drug development.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry
  • Benzenesulfonamides
  • Catalytic Domain
  • Computer Simulation
  • Conserved Sequence
  • Cyclization
  • Dihydropteroate Synthase / chemistry
  • Drug Design
  • Fluorine Compounds / chemical synthesis*
  • Fluorine Compounds / chemistry
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Molecular Structure
  • Plasmodium falciparum / enzymology
  • Protein Binding
  • Sulfadiazine / chemistry
  • Sulfadoxine / chemistry
  • Sulfalene / chemistry
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / chemistry
  • Thermodynamics
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry

Substances

  • Antimalarials
  • Fluorine Compounds
  • Sulfonamides
  • Triazoles
  • Sulfadiazine
  • Sulfadoxine
  • Dihydropteroate Synthase
  • Sulfalene