Design and synthesis of dihydroindazolo[5,4-a]pyrrolo[3,4-c]carbazole oximes as potent dual inhibitors of TIE-2 and VEGF-R2 receptor tyrosine kinases

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1916-21. doi: 10.1016/j.bmcl.2008.02.001. Epub 2008 Feb 7.

Abstract

Fused dihydroindazolopyrrolocarbazole oximes have been identified as low nanomolar, potent dual TIE-2 and VEGF-R2 receptor tyrosine kinase inhibitors with excellent cellular potency. Development of the structure-activity relationships (SAR) led to identification of compounds 35 and 40 as potent, selective dual TIE-2/VEGF-R2 inhibitors with favorable pharmacokinetic properties. Compound 35 was orally active in tumor models with no observed toxicity.

MeSH terms

  • Administration, Oral
  • Angiogenesis Inhibitors / chemical synthesis
  • Angiogenesis Inhibitors / pharmacokinetics
  • Angiogenesis Inhibitors / pharmacology
  • Animals
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Drug Design*
  • Endothelium, Vascular / cytology
  • Endothelium, Vascular / drug effects
  • Endothelium, Vascular / metabolism
  • Hemangiosarcoma / blood supply
  • Hemangiosarcoma / drug therapy
  • Hemangiosarcoma / enzymology
  • Humans
  • Melanoma, Experimental / blood
  • Melanoma, Experimental / blood supply
  • Melanoma, Experimental / drug therapy*
  • Melanoma, Experimental / enzymology
  • Molecular Structure
  • Neovascularization, Pathologic
  • Oximes / chemical synthesis*
  • Oximes / pharmacokinetics
  • Oximes / pharmacology*
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / pharmacokinetics
  • Protein Kinase Inhibitors / pharmacology*
  • Rats
  • Receptor, TIE-2 / antagonists & inhibitors*
  • Receptor, TIE-2 / metabolism
  • Structure-Activity Relationship
  • Umbilical Veins
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Vascular Endothelial Growth Factor Receptor-2 / metabolism

Substances

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