5-Phenyl-3-ureidobenzazepin-2-ones as cholecystokinin-B receptor antagonists
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...
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| Veröffentlicht in: | Journal of medicinal chemistry 1994-10, Vol.37 (22), p.3789-3811 |
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| container_end_page | 3811 |
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| container_issue | 22 |
| container_start_page | 3789 |
| container_title | Journal of medicinal chemistry |
| container_volume | 37 |
| creator | Lowe, 3rd, J A Hageman, D L Drozda, S E McLean, S Bryce, D K Crawford, R T Zorn, S Morrone, J Bordner, J |
| description | 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. |
| doi_str_mv | 10.1021/jm00048a015 |
| format | Article |
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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. 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| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1994-10, Vol.37 (22), p.3789-3811 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Animals Benzazepines - pharmacology Crystallography, X-Ray Gastric Acid - metabolism Guinea Pigs In Vitro Techniques Magnetic Resonance Spectroscopy Male Pentagastrin - pharmacology Rats Rats, Sprague-Dawley Receptor, Cholecystokinin B Receptors, Cholecystokinin - antagonists & inhibitors Structure-Activity Relationship |
| title | 5-Phenyl-3-ureidobenzazepin-2-ones as cholecystokinin-B receptor antagonists |
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