Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies

Kwong, Huey Chong and Chidan Kumar, C. S. and Mah, Siau Hui and Chia, Tze Shyang and Quah, Ching Kheng and Loh, Zi Han and Chandraju, S. and Lim, Gin Keat (2017) Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies. PLOS ONE, 12 (2). pp. 1-18. ISSN 1932-6203

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Abstract

Biphenyl-based compounds are clinically important for the treatments of hypertension and inflammatory, while many more are under development for pharmaceutical uses. In the present study, a series of 2-(1,1'-biphenyl-4-yl)-2-oxoethyl benzoates, 2(a-q), and 2-(1,1'-biphenyl-4-yl)-2-oxoethyl pyridinecarboxylate, 2(r-s) were synthesized by reacting 1-(1,1'-biphenyl-4-yl)-2-bromoethan-1-one with various carboxylic acids using potassium carbonate in dimethylformamide at ambient temperature. Single-crystal X-ray diffraction studies revealed a more closely packed crystal structure can be produced by introduction of biphenyl moiety. Five of the compounds among the reported series exhibited significant anti-tyrosinase activities, in which 2p, 2r and 2s displayed good inhibitions which are comparable to standard inhibitor kojic acid at concentrations of 100 and 250 μg/mL. The inhibitory effects of these active compounds were further confirmed by computational molecular docking studies and the results revealed the primary binding site is active-site entrance instead of inner copper binding site which acted as the secondary binding site.

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	PG Centre Mandya > Sugar Technology
Depositing User:	C Swapna Library Assistant
Date Deposited:	25 Jun 2019 09:31
Last Modified:	28 Jun 2019 05:20
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3816

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