Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors

Farmaco. 2001 Aug;56(8):555-64. doi: 10.1016/s0014-827x(01)01071-0.

Abstract

A series of new N-substituted anthranilic acid dimer derivatives having a C-terminal Phe residue was synthesized and evaluated for their affinity for CCK receptors. These compounds resulted from a blended approach based firstly on the use of an alternative substructure embedded within asperlicin and secondly on the derivatization of this template with substituents chosen considering the C-terminal primary structure of the endogenous ligand. Although these compounds exhibited a regnylogical-type organization similar to that of CCK-4, they are characterized by about 1000-fold greater affinity for CCK-A receptor than the C-terminal tetrapeptide.

MeSH terms

  • Animals
  • Benzodiazepinones / pharmacology
  • Dimerization
  • Guinea Pigs
  • Models, Molecular*
  • Rats
  • Receptors, Cholecystokinin / antagonists & inhibitors*
  • Receptors, Cholecystokinin / metabolism
  • Structure-Activity Relationship
  • ortho-Aminobenzoates / chemical synthesis*
  • ortho-Aminobenzoates / chemistry
  • ortho-Aminobenzoates / pharmacology

Substances

  • Benzodiazepinones
  • Receptors, Cholecystokinin
  • ortho-Aminobenzoates
  • asperlicin