Discovery of novel benzimidazoles as potent inhibitors of TIE-2 and VEGFR-2 tyrosine kinase receptors

J Med Chem. 2007 Sep 6;50(18):4453-70. doi: 10.1021/jm0611051. Epub 2007 Aug 4.

Abstract

We herein disclose a novel chemical series of benzimidazole-ureas as inhibitors of VEGFR-2 and TIE-2 kinase receptors, both of which are implicated in angiogenesis. Structure-activity relationship (SAR) studies elucidated a critical role for the N1 nitrogen of both the benzimidazole (segment E) and urea (segment B) moieties. The SAR results were also supported by the X-ray crystallographic elucidation of the role of the N1 nitrogen and the urea moiety when the benzimidazole-urea compounds were bound to the VEGFR-2 enzyme. The left side phenyl ring (segment A) occupies the backpocket where a 3-hydrophobic substituent was favored for TIE-2 activity.

MeSH terms

  • Animals
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology
  • Binding Sites
  • Crystallography, X-Ray
  • Humans
  • Mice
  • Models, Molecular*
  • Molecular Structure
  • NIH 3T3 Cells
  • Phosphorylation
  • Receptor, TIE-2 / antagonists & inhibitors*
  • Receptor, TIE-2 / metabolism
  • Structure-Activity Relationship
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / chemistry

Substances

  • Benzimidazoles
  • Receptor, TIE-2
  • Vascular Endothelial Growth Factor Receptor-2