Novel, achiral 1,3,4-benzotriazepine analogues of 1,4-benzodiazepine-based CCK(2) antagonists that display high selectivity over CCK(1) receptors

J Med Chem. 2006 Apr 6;49(7):2253-61. doi: 10.1021/jm051219x.

Abstract

A series of 1,3,4-benzotriazepine-based CCK(2) antagonists have been devised by consideration of the structural features that govern CCK receptor affinity and the receptor subtype selectivity of 1,4-benzodiazepine-based CCK(2) antagonists. In contrast to the latter compounds, these novel 1,3,4-benzotriazepines are achiral, yet they display similar affinity for CCK(2) receptors to the earlier molecules and are highly selective over CCK(1) receptors.

MeSH terms

  • Animals
  • Benzazepines / chemical synthesis*
  • Benzazepines / chemistry
  • Benzazepines / pharmacology
  • Benzodiazepines / chemistry
  • Cell Line
  • Cricetinae
  • Cricetulus
  • Crystallography, X-Ray
  • Humans
  • Mice
  • Molecular Structure
  • Radioligand Assay
  • Rats
  • Receptor, Cholecystokinin A / antagonists & inhibitors*
  • Receptor, Cholecystokinin A / chemistry
  • Receptor, Cholecystokinin B / antagonists & inhibitors*
  • Receptor, Cholecystokinin B / chemistry
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Benzazepines
  • Receptor, Cholecystokinin A
  • Receptor, Cholecystokinin B
  • Benzodiazepines
  • Bz-423