Design and synthesis of 3,3'-biscoumarin-based c-Met inhibitors

Org Biomol Chem. 2014 Jun 14;12(22):3721-34. doi: 10.1039/c4ob00364k. Epub 2014 Apr 30.

Abstract

A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3'-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met and EBC-1 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphate / pharmacology
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Drug Design*
  • Humans
  • Inhibitory Concentration 50
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Proto-Oncogene Proteins c-met / antagonists & inhibitors*
  • Umbelliferones / chemical synthesis
  • Umbelliferones / chemistry
  • Umbelliferones / pharmacology

Substances

  • Coumarins
  • N-(1-((7,8-dihydroxy-2-oxo-2H-chromen-3-yl)amino)-1-oxoheptan-2-yl)-7,8-dihydroxy-2-oxo-2H-chromene-3-carboxamide
  • N-(1-((7,8-dihydroxy-2-oxo-2H-chromen-3-yl)amino)-1-oxooctan-2-yl)-7,8-dihydroxy-2-oxo-2H-chromene-3-carboxamide
  • Protein Kinase Inhibitors
  • Umbelliferones
  • Adenosine Triphosphate
  • Proto-Oncogene Proteins c-met
  • daphnetin