New halogenated phenylcoumarins as tyrosinase inhibitors

Bioorg Med Chem Lett. 2011 Jun 1;21(11):3342-5. doi: 10.1016/j.bmcl.2011.04.012. Epub 2011 Apr 9.

Abstract

With the aim to find out structural features for the tyrosinase inhibitory activity, in the present communication we report the synthesis and pharmacological evaluation of a new series of phenylcoumarin derivatives with different number of hydroxyl or ether groups and bromo substituent in the scaffold. The synthesized compounds 5-12 were evaluated as mushroom tyrosinase inhibitors showing, two of them, lower IC(50) than the umbelliferone. Compound 12 (IC(50)=215 μM) is the best tyrosinase inhibitor of this series.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agaricales / enzymology
  • Bromine / chemistry*
  • Coumarins / chemistry*
  • Coumarins / pharmacology*
  • Enzyme Activation / drug effects
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*

Substances

  • Coumarins
  • Enzyme Inhibitors
  • 4-phenylcoumarin
  • Monophenol Monooxygenase
  • Bromine