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5-Phenyl-3-ureidobenzazepin-2-ones as Cholecystokinin-B Receptor Antagonists
Journal of Medicinal Chemistry1994Vol. 37(22), pp. 3789–3811
Citations Over TimeTop 24% of 1994 papers
John Lowe, David Hageman, Susan E. Drozda, Stafford McLean, Dianne K. Bryce, Rosemary T. Crawford, Stevin H. Zorn, Jean Morrone, Jon Bordner
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.
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