Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility

J Med Chem. 1986 Oct;29(10):1941-5. doi: 10.1021/jm00160a024.


Seventeen analogues of the selective, competitive cholecystokinin (CCK) antagonist asperlicin 1 were prepared. These compounds were tested as inhibitors of the binding of [125I]CCK to rat pancreas and guinea pig brain receptors. Compounds 4, 7, and 8 were more potent than asperlicin on the pancreatic CCK receptor. One analogue, 17, displayed potency equivalent to asperlicin on the pancreas CCK receptor and showed a marked improvement in aqueous solubility, thereby facilitating the use of this class of CCK antagonists in physiological and pharmacological studies.

MeSH terms

  • Animals
  • Benzodiazepinones / chemical synthesis*
  • Benzodiazepinones / pharmacology
  • Cholecystokinin / antagonists & inhibitors*
  • Guinea Pigs
  • In Vitro Techniques
  • Rats
  • Receptors, Cholecystokinin / drug effects
  • Solubility
  • Structure-Activity Relationship


  • Benzodiazepinones
  • Receptors, Cholecystokinin
  • Cholecystokinin
  • asperlicin