A novel class of highly potent and selective A1 adenosine antagonists: Structure-affinity profile of a series of 1,8-naphthyridine derivatives

Journal of Medicinal Chemistry

Volumn 43, Issue 15, 2000, Pages 2814-2823

  Ferrarini, Pier Luigi ^a   Mori, Claudio ^a   Manera, Clementina ^a   Martinelli, Adriano ^a   Mori, Filippo ^a   Saccomanni, Giuseppe ^a   Barili, Pier Luigi ^a   Betti, Laura ^a   Giannaccini, Gino ^a   Trincavelli, Letizia ^a   Lucacchini, Antonio ^a  

^a UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 NAPHTHYRIDINE DERIVATIVE; ADENOSINE RECEPTOR BLOCKING AGENT; ADENYLATE CYCLASE; NAPHTHYRIDINE DERIVATIVE; OXYGEN;

ARTICLE; BINDING AFFINITY; BRAIN MEMBRANE; DRUG POTENCY; NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THEORY;

ADENYLATE CYCLASE; ANIMALS; CATTLE; CEREBRAL CORTEX; CORPUS STRIATUM; MAGNETIC RESONANCE SPECTROSCOPY; MALE; NAPHTHYRIDINES; RADIOLIGAND ASSAY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, ADENOSINE A2A; RECEPTOR, ADENOSINE A3; RECEPTORS, PURINERGIC P1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 17144441273     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990321p     Document Type: Article

References (36)

1. Jacobson, K. A., Daly, J. W., Manganiello, V., Eds. Purine in Cellular Signaling - Targets for New Drugs; Springer-Verlag: New York, 1990.
2. 2 Receptors: Structure - Function Relationships. Med. Res. Rev. 1992, 12, 423-471.
3. Jacobson, K. A.; Van Galen, P. J. M.; Williams, M. Adenosine Receptors - Pharmacology, Structure Activity Relationships and Therapeutic Potential. J. Med. Chem. 1992, 35, 407-422.
4. von Lubitz, D. K. J. E.; Jacobson, K. A. Behavioral Effects of Adenosine Receptor Stimulation. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Belardinelli, L., Pelleg, A., Eds.; Kluwer: Norwell, MA, 1995; pp 489-498.
5. Jacobson, M. Cloning and Expression of Human Adenosine Receptor Subtypes. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Belardinelli, L., Pelleg, A., Eds.; Kluwer: Norwell, MA, 1995; pp 5-13.
6. Daly, J. W.; Jacobson, K. A. Adenosine Receptors: Selective Agonists and Antagonists. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Belardinelli, L., Pelleg, A., Eds.; Kluwer: Norwell, MA, 1995; pp 157-166.
7. Linden, J.; Jacobson, M. A.; Hutchins, C.; Williams, M. Adenosine Receptors. In Handbook of Receptors Channels; Peroutka, S. J., Eds.; CRC Press: Boca Raton, FL, 1994; Vol. 1, pp 29-44.
8. Fredholm, B. B.; Abbracchio, M. P.; Burnstock, G.; Daly, J. W.; Harden, T. K.; Jacobson, K. A.; Leff, P.; Williams, M. Nomenclature and classification of purinoceptors. Pharmacol. Rev. 1994, 46, 143-156.
9. 2 receptors. Can. J. Physiol. Pharmacol. 1987, 65, 365-376.
10. 2A Adenosine Antagonists. J. Med. Chem. 1996, 39, 1164-1171.
11. 2A adenosine receptor antagonist. J. Pharmacol. Exp. Ther. 1996, 276, 398-404.
12. 2A adenosine receptor antagonist. J. Med. Chem. 1998, 41, 2126-2133.
13. Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. Structure-Activity Profile of a Series of Novel Triazoloquinazoline Adenosine Antagonists. J. Med. Chem. 1988, 31, 1014-1020.
14. 1 Antagonists. 2. Structure-Activity Relationships on Diuretic Activities and Protective Effects against Acute Renal Failure. J. Med. Chem. 1992, 35, 3066-3075.
15. 3 Adenosine Receptor Antagonists. J. Med. Chem. 1996, 39, 2293-2301.
16. 2A adenosine binding activity of some pyrano[2,3-c]pyrazol-4-ones. Farmaco 1998, 53, 189-196.
17. van Rhee, A. M.; Siddiqi, S. M.; Melman, N.; Shi, D.; Padget, W. L.; Daly, J. W.; Jacobson, K. A. Tetrahydrobenzothiophenone Derivatives as a Novel Class of Adenosine Receptor Antagonists. J. Med. Chem. 1996, 39, 398-406.
18. Ji, X.; Melman, N.; Jacobson, K. A. Interactions of Flavonoids and Other Phytochemicals with Adenosine Receptors. J. Med. Chem. 1996, 39, 781-788.
19. 3 Receptor Ligands. 2. Structure Affinity Profile of a Series of Isoquinoline and Quinazoline Compounds. J. Med. Chem. 1998, 41, 3994-4000.
20. 2-adenosine receptors. Pharmazie 1994, 49, 878-880.
21. Carboni, S.; Da Settimo, A.; Ferrarini, P. L.; Livi, O. Preparazione e studio farmacologico di alcuni derivati 1,2,3-triazol-1,8-naftiridinici. Farmaco Ed. Sci. 1978, 33, 315-323.
22. Ferrarini, P. L.; Mon, C.; Manera, C.; Mori, F.; Calderone, C.; Martinotti, E. Condensation of Substituted 2-aminopyridine with β-Ketocarboxylic esters: 4H-Pyrido[1,2-a]pyrimidin-4-ones and Pyridin-2-ones. J. Heterocycl. Chem., in press.
23. Ferrarini, P. L.; Mori, C.; Livi, O.; Biagi, G.; Marini, A. M. Synthesis of some Substituted Pyrido[1,2-a]pyrimidin-4-ones and 1,8-naphthyridines. J. Heterocycl. Chem. 1983, 20, 1053-1057.
24. Ferrarini, P. L.; Mori, C.; Primofiore, G.; Calzolari, L. One Step Synthesis of Pyrimido[1,2-a][1,8]naphthyridinones, Pyrido[1,2-a]pyrimidinones and 1,8-Naphthyridinones. Antihypertensive Agents. V. J. Heterocycl. Chem. 1990, 27, 881-886.
25. Carboni, S.; Da Settimo, A.; Pirisino, G.; Segnini, D. Ricerche nel campo delle naftiridine. Precisazioni sulla reazione tra 2,6-diaminopiridina e acetoacetato di etile. Gaz. Chim. Ital. 1966, 96, 103-113.
26. Brown, E. V. 1,8-Naphthyridine. I. Derivatives of 2- and 4-Methyl-1,8-naphthyridines. J. Org. Chem. 1965, 30, 1607-1610.
27. Da Settimo, A.; Ferrarini, P. L.; Mori, C.; Primofiore, G.; Subissi, A. Synthesis of 1,8-naphthyridine derivatives. Potential anti-hypertensive agents. II. Farmaco Ed. Sci. 1986, 41, 827-838.
28. Ferrarini, P. L.; Livi, O.; Menichetti, V. M. Preparazione ed esame farmacologico di alcuni derivati 1,8-nafliridin-4-idrazonici. Farmaco Ed. Sci. 1979, 34, 165-169.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raaghavachari, K.; AlLaham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, K. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, B. J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 w, version 4.0; Gaussian, Inc.: Pittsburgh, PA, 1995.
30. 1 binding sites from sheep cortex. Neurochem. Int. 1985, 7, 1017-1020.
31. 2+ ion. Biochim. Biophys. Acta 1993, 1220, 76-84.
32. 6-substituted Adenosine Derivatives in Rat Testis Membranes. J. Recept. Sign. Transd. Res. 1995, 15, 905-929.
33. Franchetti, P.; Cappellacci, L.; Marchetti, S.; Trincavelli, L.; Martini, C.; Mazzoni, M. R.; Lucacchini, A.; Grifantini, M. 2′C-Methyl Analogues of Selective Adenosine Receptor Agonists: Synthesis and Binding Studies. J. Med. Chem. 1998, 41, 1708-1715.
34. 50) of an Enzyme Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
35. Peterson, G. L. A simplification of the protein assay method of Lowry et al. which is more generally applicable. Anal. Biochem. 1977, 83, 356-366.
36. Johnson, R. G.; Aklvarez, R.; Salomon, Y. Determination of adenylyl cyclase catalytic activity using single and double column procedures. Methods Enzymol. 1994, 238, 31-56.