Discovery of imidazole vinyl pyrimidines as a novel class of kinase inhibitors which inhibit Tie-2 and are orally bioavailable

Bioorg Med Chem Lett. 2008 Aug 15;18(16):4723-6. doi: 10.1016/j.bmcl.2008.06.106. Epub 2008 Jul 23.

Abstract

Tie-2 is a receptor tyrosine kinase which is involved in angiogenesis and thereby growth of human tumours. The discovery and SAR of a novel class of imidazole-vinyl-pyrimidine kinase inhibitors, which inhibit Tie-2 in vitro is reported. Their synthesis was carried out by condensation of imidazole aldehydes with methyl pyrimidines. These compounds are lead-like, with low molecular weight, good physical properties and oral bioavailability.

MeSH terms

  • Administration, Oral
  • Biological Availability
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Humans
  • Imidazoles / administration & dosage
  • Imidazoles / chemical synthesis*
  • Inhibitory Concentration 50
  • Models, Chemical
  • Molecular Conformation
  • Neovascularization, Pathologic
  • Protein Kinase Inhibitors / administration & dosage
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrimidines / administration & dosage
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology*
  • Receptor, TIE-2 / antagonists & inhibitors*
  • Receptor, TIE-2 / chemistry
  • Structure-Activity Relationship

Substances

  • Imidazoles
  • Protein Kinase Inhibitors
  • Pyrimidines
  • Receptor, TIE-2
  • pyrimidine