Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells

Eur J Med Chem. 2010 Dec;45(12):5567-75. doi: 10.1016/j.ejmech.2010.09.006. Epub 2010 Sep 17.

Abstract

We report the synthesis of a novel series of highly potent melanin inhibitors which were obtained through structural modification of an anticancer compound S-(+)-decursinol. The in vitro inhibitory potencies of the newly synthesized compounds were evaluated against α-MSH induced melanin production in B16 murine melanoma cells. Among the compounds evaluated, compounds 2, 3, 6b, 7a, 7b, 8a and 8b emerged as highly potent inhibitors of melanin production. Besides, these compounds demonstrated significantly low cytotoxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Benzopyrans / toxicity
  • Butyrates / chemical synthesis
  • Butyrates / chemistry
  • Butyrates / pharmacology*
  • Butyrates / toxicity
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Melanins / biosynthesis*
  • Melanoma, Experimental / metabolism*
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Structure
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Benzopyrans
  • Butyrates
  • Melanins
  • decursin