Synthesis of novel compounds as new potent tyrosinase inhibitors

Biomed Res Int. 2013:2013:207181. doi: 10.1155/2013/207181. Epub 2013 Oct 22.

Abstract

In the present paper, we report the synthesis and pharmacological evaluation of a new series of azo compounds with different groups (1-naphthol, 2-naphthol, and N,N-dimethylaniline) and trifluoromethoxy and fluoro substituents in the scaffold. All synthesized compounds (5a-5f) showed the most potent mushroom tyrosinase inhibition (IC₅₀ values in the range of 4.39 ± 0.76-1.71 ± 0.49 µM), comparable to the kojic acid, as reference standard inhibitor. All the novel compounds were characterized by FT-IR, ¹H NMR, ¹³C NMR, and elemental analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Azo Compounds / chemical synthesis*
  • Azo Compounds / chemistry
  • Azo Compounds / pharmacology*
  • Azo Compounds / toxicity
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Enzyme Inhibitors / toxicity
  • Melanins / biosynthesis
  • Mice
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Spectrophotometry, Ultraviolet

Substances

  • Azo Compounds
  • Enzyme Inhibitors
  • Melanins
  • Monophenol Monooxygenase