Tyrosinase inhibitory effect of benzoic acid derivatives and their structure-activity relationships.
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.
Khan
Sher Bahadar
SB
Department of Chemical and Biomolecular Engineering, Yonsei University, 262 Seongsanno, Seodaemun-gu, Seoul, South Korea.
Hassan Khan
Mahmud Tareq
MT
Jang
Eui Sung
ES
Akhtar
Kalsoom
K
Seo
Jongchul
J
Han
Haksoo
H
D015761:4-Aminopyridine / Q000031:analogs & derivatives / Q000737:chemistry; D001549:Benzamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001565:Benzoates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007700:Kinetics; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
D001549:Benzamides; D001565:Benzoates; D004791:Enzyme Inhibitors; C556779:N-(2-hydroxy-ethyl)-3,5-dinitro-benzamide; D004024:Dicyclohexylcarbodiimide; D015761:4-Aminopyridine; D014442:Monophenol Monooxygenase; C003885:4-dimethylaminopyridine