Synthesis of N-terminal substituted anthranilic acid dimer derivatives for evaluation on CCK receptors.
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.
Varnavas
A
A
Department of Pharmaceutical Sciences, University of Trieste, Italy. varnavas@univ.trieste.it
Valenta
V
V
Berti
F
F
Lassiani
L
L
D000818:Animals; D001570:Benzodiazepinones / Q000494:pharmacology; D019281:Dimerization; D006168:Guinea Pigs; D008958:Models, Molecular; D051381:Rats; D011949:Receptors, Cholecystokinin / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship; D062367:ortho-Aminobenzoates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D001570:Benzodiazepinones; D011949:Receptors, Cholecystokinin; D062367:ortho-Aminobenzoates; C046367:asperlicin