Synthesis, SAR, and Evaluation of 4-[2,4-Difluoro-5-(cyclopropylcarbamoyl)phenylamino]pyrrolo[2,1-f][1,2,4]triazine-based VEGFR-2 kinase inhibitors

Bioorg Med Chem Lett. 2008 Feb 15;18(4):1354-8. doi: 10.1016/j.bmcl.2008.01.012. Epub 2008 Jan 9.

Abstract

Introduction of the 2,4-difluoro-5-(cyclopropylcarbamoyl)phenylamino group at the C-4 position of the pyrrolo[2,1-f][1,2,4] triazine scaffold led to the discovery of a novel sub-series of inhibitors of VEGFR-2 kinase activity. Subsequent SAR studies on the 1,3,5-oxadiazole ring appended to the C-6 position of this new sub-family of pyrrolotriazines resulted in the identification of low nanomolar inhibitors of VEGFR-2. Antitumor efficacy was observed with compound 37 against L2987 human lung carcinoma xenografts in athymic mice.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry*
  • Cyclopropanes / pharmacology*
  • Cytochrome P-450 Enzyme Inhibitors
  • Endothelial Cells / cytology
  • Endothelial Cells / drug effects
  • Humans
  • Lung Neoplasms / drug therapy
  • Mice
  • Mice, Nude
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology
  • Protein Kinase Inhibitors / chemical synthesis*
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / pharmacology*
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Structure-Activity Relationship
  • Triazines / chemical synthesis
  • Triazines / chemistry*
  • Triazines / pharmacology*
  • Vascular Endothelial Growth Factor Receptor-2 / antagonists & inhibitors*
  • Xenograft Model Antitumor Assays

Substances

  • Cyclopropanes
  • Cytochrome P-450 Enzyme Inhibitors
  • Oxadiazoles
  • Protein Kinase Inhibitors
  • Pyrroles
  • Triazines
  • Vascular Endothelial Growth Factor Receptor-2