Design, synthesis and evaluation of novel benzimidazoles, benzothiazoles and benzofurans incorporating pyrazole moiety as antiangiogenic agents

Arzneimittelforschung. 2012 Feb;62(2):63-74. doi: 10.1055/s-0031-1295483. Epub 2012 Feb 16.

Abstract

Novel benzimidazoles, benzothiazoles and benzofurans incorporating pyrazole moiety have been synthesized and screened for their antiangogenic activities, by testing their ability to inhibit human umbilical vein endothelial cell (HUVEC) proliferation, cord formation and migration in response to chemoattractant. 3 compounds 19, 23 and 26 showed antiangiogenic activities at non-cytotoxic concentrations. Compound 19 was the most active with chemotaxis activity data nearly comparable to that of the positive control, TNP-470. Compound 42 showed a significant cytotoxic effect on the tested cancer cell lines and less antiangiogenesis activity compared to compounds 19, 23 and 26. All the tested compounds, in contrary to TNP-470, interfered with the migratory function of HUVECs in response to vascular endothelial growth factor rather than the endothelial cells proliferation or cord formation. Moreover, a docked pose of compounds 19 and 26 was obtained bound to kinase insert domain receptor using Molecular Operating Environment module.

MeSH terms

  • Angiogenesis Inhibitors / chemical synthesis*
  • Angiogenesis Inhibitors / pharmacology*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / pharmacology*
  • Benzofurans / chemical synthesis*
  • Benzofurans / pharmacology*
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Endothelial Cells / drug effects
  • Human Umbilical Vein Endothelial Cells
  • Humans
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Pyrazoles
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship

Substances

  • Angiogenesis Inhibitors
  • Benzimidazoles
  • Benzofurans
  • Benzothiazoles
  • Indicators and Reagents
  • Pyrazoles
  • pyrazole