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

Abstract

A series of benzoic acid derivatives 110 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 structureactivity relationships of the synthesised molecules. © 2010 Informa UK, Ltd.