8-THP-DHI analogs as potent Type I dual TIE-2/VEGF-R2 receptor tyrosine kinase inhibitors

Bioorg Med Chem Lett. 2010 Jun 1;20(11):3356-60. doi: 10.1016/j.bmcl.2010.04.021. Epub 2010 Apr 13.

Abstract

A novel series of 8-(2-tetrahydropyranyl)-12,13-dihydroindazolo[5,4-a]pyrrolo[3,4-c]carbazoles (THP-DHI) was synthesized and evaluated as dual TIE-2 and VEGF-R2 receptor tyrosine kinase inhibitors. Development of the structure-activity relationships (SAR) with the support of X-ray crystallography led to identification of 7f and 7g as potent, selective dual TIE-2/VEGF-R2 inhibitors with excellent cellular potency and acceptable pharmacokinetic properties. Compounds 7f and 7g were orally active in tumor models with no observed toxicity.

MeSH terms

  • Animals
  • Cells, Cultured
  • Crystallography, X-Ray
  • Humans
  • Models, Molecular
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • Receptor, TIE-2 / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*

Substances

  • Protein Kinase Inhibitors
  • Receptor, TIE-2
  • Vascular Endothelial Growth Factor Receptor-2