Discovery and structure-activity relationship of the first non-peptide competitive human glucagon receptor antagonists

J Med Chem. 1998 Dec 17;41(26):5150-7. doi: 10.1021/jm9810304.

Abstract

The first non-peptide competitive human glucagon receptor antagonist, 2-(benzimidazol-2-ylthio)-1-(3,4-dihydroxyphenyl)-1-ethan one, NNC 92-1687 (2), is described. This antagonist has a binding affinity of 20 microM (IC50) and a functional Ki = 9.1 microM at the human glucagon receptor. A structure-activity relationship (SAR) was obtained on this compound, and the results show that only the benzimidazole part can be changed without complete loss of affinity. Analogues with tert-butyl or benzyloxy groups in the 5-position of the benzimidazole moiety were found to be equipotent or slightly more potent, all displaying binding affinities around 5-20 microM. Most of the changes to the catechol and the linker gave compounds without any affinity toward the human glucagon receptor. The 3-hydroxy group could, however, in the presence of a 4-hydroxy group be changed to a methoxy or a chloro group while retaining affinity.

MeSH terms

  • Animals
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzimidazoles / metabolism
  • Cell Line
  • Cricetinae
  • Humans
  • Receptors, Glucagon / antagonists & inhibitors*
  • Structure-Activity Relationship

Substances

  • 2-(benzimidazo-2-ylthio)-1-(3,4-dihydroxyphenyl)-1-ethanone
  • Benzimidazoles
  • Receptors, Glucagon