ortho-Substituted azoles as selective and dual inhibitors of VEGF receptors 1 and 2

Bioorg Med Chem Lett. 2007 Mar 1;17(5):1369-75. doi: 10.1016/j.bmcl.2006.11.087. Epub 2006 Dec 2.

Abstract

We have developed a series of novel potent ortho-substituted azole derivatives active against kinases VEGFR-1 and VEGFR-2. Both specific and dual ATP-competitive inhibitors of VEGFR-2 were identified. Kinase activity and selectivity could be controlled by varying the arylamido substituents at the azole ring. The most specific molecule (17) displayed > 10-fold selectivity for VEGFR-2 over VEGFR-1. Compound activities in enzymatic and cell-based assays were in the range of activities for reported clinical and development candidates (IC50 < 100 nM), including Novartis' PTK787 (Vatalanib). High permeability of active compounds across the Caco-2 cell monolayer (> 30x10(-5) cm/min) is indicative of their potential for intestinal absorption upon oral administration.

MeSH terms

  • Adenosine Triphosphate / metabolism
  • Azoles / chemical synthesis*
  • Azoles / pharmacokinetics
  • Azoles / pharmacology*
  • Binding, Competitive
  • Caco-2 Cells
  • Cell Membrane Permeability
  • Humans
  • Inhibitory Concentration 50
  • Intestinal Absorption
  • Structure-Activity Relationship
  • Substrate Specificity
  • Vascular Endothelial Growth Factor Receptor-1 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*

Substances

  • Azoles
  • Adenosine Triphosphate
  • Vascular Endothelial Growth Factor Receptor-1
  • Vascular Endothelial Growth Factor Receptor-2