5-Phenyl-3-ureidobenzazepin-2-ones as Cholecystokinin-B Receptor Antagonists
- 1 October 1994
- journal article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 37 (22) , 3789-3811
- https://doi.org/10.1021/jm00048a015
Abstract
A series of 5-phenyl-3-ureidobenzazepin-2-one cholecystokinin-B (CCK-B) receptor antagonists was synthesized using Beckmann ring expansion of a suitable 4-phenyl-1-tetralone as a key step. Structure-activity relationship studies revealed the importance of the 5-phenyl group for potent and selective CCK-B affinity. Addition of an 8-methyl substituent and resolution provided the potent (CCK-B IC50 = 0.48 nM) CCK-B antagonist 4. The role of the 5-phenyl group as part of a "privileged structure" for high-affinity receptor antagonism is discussed.Keywords
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