Design, synthesis and molecular simulation studies of dihydrostilbene derivatives as potent tyrosinase inhibitors

Bioorg Med Chem Lett. 2012 Sep 1;22(17):5523-6. doi: 10.1016/j.bmcl.2012.07.029. Epub 2012 Jul 14.

Abstract

The synthesis, molecular modeling and biological evaluation of substituted deoxybenzoins and optimized dihydrostilbenes are reported. Preliminary structure-activity relationship data were elucidated and lead compounds suitable for further optimization were discovered. Dihydrostilbene 7 is a particularly potent inhibitor (IC(50)=8.44 μM, more potent than kojic acid).

MeSH terms

  • Bacteria / enzymology
  • Benzoin / analogs & derivatives*
  • Benzoin / chemical synthesis
  • Benzoin / chemistry
  • Benzoin / pharmacology
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Fungi / enzymology
  • Molecular Docking Simulation
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pyrones / chemistry
  • Pyrones / pharmacology
  • Stilbenes / chemical synthesis
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Pyrones
  • Stilbenes
  • 1,2-dihydrostilbene
  • kojic acid
  • Monophenol Monooxygenase
  • deoxybenzoin
  • Benzoin