Tyrosinase inhibitory effect of benzoic acid derivatives and their structure-activity relationships

J Enzyme Inhib Med Chem. 2010 Dec;25(6):812-7. doi: 10.3109/14756366.2010.482529. Epub 2010 May 17.

Abstract

A series of benzoic acid derivatives 1-10 have been synthesised by two different methods. Compounds 1-6 were synthesised by a facile procedure for esterification using N,N'-dicyclohexylcarbodiimide (DCC) as a coupling agent, methylene chloride as a solvent system and dimethylaminopyridine (DMAP). While 7-10 were synthesised by converting benzoic acid into benzoyl chloride by treating with thionyl chloride in the presence of benzene and performing a further reaction with amine in dried benzene. The structures of all the synthesised derivatives of benzoic acid (1-10) were assigned on the basis of extensive NMR studies. All of them showed inhibitory potential against tyrosinase. Among them, compound 7 was found to be the most potent (1.09 μM) when compared with the standard tyrosinase inhibitors of kojic acid (16.67 μM) and L-mimosine (3.68 μM). Finally in this paper, we have discussed the structure-activity relationships of the synthesised molecules.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Aminopyridine / analogs & derivatives
  • 4-Aminopyridine / chemistry
  • Benzamides / chemical synthesis
  • Benzamides / chemistry
  • Benzamides / pharmacology
  • Benzoates / chemical synthesis
  • Benzoates / chemistry*
  • Benzoates / pharmacology*
  • Dicyclohexylcarbodiimide / chemistry
  • Drug Design*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Kinetics
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • Benzamides
  • Benzoates
  • Enzyme Inhibitors
  • N-(2-hydroxy-ethyl)-3,5-dinitro-benzamide
  • Dicyclohexylcarbodiimide
  • 4-Aminopyridine
  • Monophenol Monooxygenase
  • 4-dimethylaminopyridine