Synthesis, characterization, and tyrosinase inhibitory properties of benzimidazole derivatives

Bioorg Khim. 2014 Jul-Aug;40(4):497-502.

Abstract

1-Alkylbenzimidazole and 1,3-dialkyl benzimidazolium salts were synthesized and characterized by the data of IR, 1H NMR, 13C NMR spectra and elemental analyses. These compounds were investigated as tyrosinase inhibitors. Tyrosinase has been purified from banana by affinity chromatography on a Sepharose 4B gel conjugated with L-tyrosine-p-aminobenzoic acid. All the synthesized compounds inhibited the tyrosinase activity. Among the compounds studied, 1,4-di(1H-benzo[d]imidazol-1-yl)butane was found to be the most active tyrosinase inhibitor (IC50 0.31 mM).

MeSH terms

  • 4-Aminobenzoic Acid
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / chemistry
  • Structure-Activity Relationship
  • Tyrosine / chemistry
  • Tyrosine / metabolism

Substances

  • Benzimidazoles
  • Enzyme Inhibitors
  • Tyrosine
  • benzimidazole
  • Monophenol Monooxygenase
  • 4-Aminobenzoic Acid