Affiliations 

  • 1 School of Chemical Sciences, Universiti Sains Malaysia, Penang, Malaysia
  • 2 Department of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahalli, Mysuru, Karnataka, India
  • 3 School of Biosciences, Taylor's University, Lakeside Campus, Subang Jaya, Selangor, Malaysia
  • 4 X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang, Malaysia
  • 5 Department of Sugar Technology & Chemistry, Sir M.V. PG Center, University of Mysore, Tubinakere, India
PLoS One, 2017;12(2):e0170117.
PMID: 28241010 DOI: 10.1371/journal.pone.0170117

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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.