Design, synthesis and biological activity of 6-substituted carbamoyl benzimidazoles as new nonpeptidic angiotensin II AT₁ receptor antagonists

Bioorg Med Chem. 2012 Jul 15;20(14):4208-16. doi: 10.1016/j.bmc.2012.05.056. Epub 2012 Jun 5.

Abstract

A series of 6-substituted carbamoyl benzimidazoles were designed and synthesised as new nonpeptidic angiotensin II AT(1) receptor antagonists. The preliminary pharmacological evaluation revealed a nanomolar AT(1) receptor binding affinity for all compounds in the series, and a potent antagonistic activity in an isolated rabbit aortic strip functional assay for compounds 6f, 6g, 6h and 6k was also demonstrated. Furthermore, evaluation in spontaneous hypertensive rats and a preliminary toxicity evaluation showed that compound 6g is an orally active AT(1) receptor antagonist with low toxicity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angiotensin II Type 1 Receptor Blockers / chemical synthesis*
  • Angiotensin II Type 1 Receptor Blockers / chemistry
  • Angiotensin II Type 1 Receptor Blockers / pharmacology
  • Animals
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry*
  • Benzimidazoles / pharmacology
  • Biphenyl Compounds / chemical synthesis
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / pharmacology
  • Blood Pressure / drug effects
  • Drug Design*
  • Models, Molecular
  • Protein Binding
  • Rabbits
  • Rats
  • Rats, Inbred SHR
  • Receptor, Angiotensin, Type 1 / chemistry*
  • Receptor, Angiotensin, Type 1 / metabolism
  • Structure-Activity Relationship

Substances

  • Angiotensin II Type 1 Receptor Blockers
  • Benzimidazoles
  • Biphenyl Compounds
  • N-(2-Phenyl)propyl-1-(2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl-4-methyl-2-n-propyl-1H-benzimidazole-6-carboxamide
  • Receptor, Angiotensin, Type 1