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.
|Number of pages||6|
|Journal||Journal of Enzyme Inhibition and Medicinal Chemistry|
|Publication status||Published - 2010 Dec|
Bibliographical noteFunding Information:
This work was supported by Korea Association of Industry, Academy and Research Institute grant funded by the Korea government (SMBA) (00037459) and National Research Foundation of Korea grant funded by the Korean Government (MEST); contract grant number; NRF-2009-C1AAA001-0092926.
All Science Journal Classification (ASJC) codes
- Drug Discovery