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Título: | Synthesis and stereochemical structure activity relationships of 1,3- dioxoperhydropyrido[1,2-c]pyrimidine derivatives: Potent and selective cholecystokinin-a receptor antagonists |
Autor: | Martín-Martínez, Mercedes CSIC ORCID; Bartolomé-Nebreda, José M.; Gómez-Monterrey, Isabel CSIC; González-Muñiz, Rosario CSIC ORCID; García-López, M. Teresa CSIC ; Ballaz García, Santiago; Barber Cárcamo, Ana María; Fortuño, Ana; Río, Joaquín del CSIC; Herranz, Rosario CSIC ORCID | Palabras clave: | Antagonists Pyrimidine Reaction products Receptors Selectivity |
Fecha de publicación: | 10-oct-1997 | Editor: | American Chemical Society | Citación: | Journal of Medicinal Chemistry 40(21): 3402 3407 (1997) | Resumen: | The synthesis and stereochemical structure-activity relationships of a new class of potent and selective non-peptide cholecystokinin-A (CCK-A) receptor antagonists based on the 1,3-dioxoperhydropyrido[1,2-c]pyrimidine skeleton are described. The most potent member of this series of eight diastereoisomers, (4aS,5R)-2-benzyl-5-[N-[(tert-butoxycarbonyl)-L- tryptophyl]-amino]-1,3-dioxoperhydropyrido[1,2-c]pyrimidine, displays nanomolar CCK-A receptor affinity and higher than 8000-fold potency at the CCK-A than at the CCK-B receptor. As CCK-A antagonist, this compound inhibits the CCK-8-evoked amylase release from pancreatic acinar cells at a low concentration, similar to that of the typical antagonist Devazepide. Highly strict stereochemical requirements for CCK-A receptor binding and selectivity have been found. The L-Trp and the 4a,5-trans disposition of the bicyclic perhydropyrido[1,2-c]pyrimidine are essential for binding potency and selectivity. | Versión del editor: | http://dx.doi.org/10.1021/jm9703247 | URI: | http://hdl.handle.net/10261/336639 | DOI: | 10.1021/jm9703247 | ISSN: | 0022-2623 | E-ISSN: | 1520-4804 |
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