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  • Title: Tyrosinase inhibitory effect of benzoic acid derivatives and their structure-activity relationships.
    Author: Khan SB, Hassan Khan MT, Jang ES, Akhtar K, Seo J, Han H.
    Journal: J Enzyme Inhib Med Chem; 2010 Dec; 25(6):812-7. PubMed ID: 20476840.
    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.
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