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

Sher Bahadar Khan, Mahmud Tareq Hassan Khan, Eui Sung Jang, Kalsoom Akhtar, Jongchul Seo, Haksoo Han

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)812-817
Number of pages6
JournalJournal of Enzyme Inhibition and Medicinal Chemistry
Volume25
Issue number6
DOIs
Publication statusPublished - 2010 Dec

Bibliographical note

Funding 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

  • Pharmacology
  • Drug Discovery

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