Synthesis and biological evaluation of kojic acid derivatives containing 1,2,4-triazole as potent tyrosinase inhibitors. Academic Article uri icon

Overview

abstract

  • A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole, and their inhibitory effects on mushroom tyrosinase were evaluated. The results indicated that most of the synthesized compounds exhibited significant inhibitory activity. Specifically, 5-(4-chlorophenyl)-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole (6j) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 4.50 ± 0.34 μm. The kinetic studies of the compound (6j) demonstrated that the inhibitory effects of the compound on the tyrosinase were belonging to competitive inhibitors. Meanwhile, the structure-activity relationship was also discussed.

publication date

  • May 14, 2015

Research

keywords

  • Agaricales
  • Enzyme Inhibitors
  • Monophenol Monooxygenase
  • Pyrones
  • Triazoles

Identity

Scopus Document Identifier

  • 84944154078

Digital Object Identifier (DOI)

  • 10.1111/cbdd.12577

PubMed ID

  • 25916324

Additional Document Info

volume

  • 86

issue

  • 5