Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives: Potent and selective A2A adenosine antagonists

Journal of Medicinal Chemistry

Volumn 39, Issue 5, 1996, Pages 1164-1171

  Baraldi, Pier Giovanni ^a   Cacciari, Barbara ^b   Spalluto, Giampiero ^b   Pineda De Las Infantas Y Villatoro, Maria José ^b   Zocchi, Cristina ^b   Dionisotti, Silvio ^b   Ongini, Ennio ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

5 AMINO 7 (3 PHENYLPROPYL) 2 (2 FURYL)PYRAZOLO [4,3 E] 1,2,4 TRIAZOLO[1,5 C]PYRIMIDINE; 5 AMINO 7 (4 PHENYLBUTYL) 2 (2 FURYL)PYRAZOLO [4,3 E] 1,2,4 TRIAZOLO[1,5 C]PYRIMIDINE; 5 AMINO 7 (BETA MORPHOLIN 4 YLETHYL) 2 (2 FURYL)PYRAZOLO [4,3 E] 1,2,4 TRIAZOLO[1,5 C]PYRIMIDINE; ADENOSINE A2 RECEPTOR ANTAGONIST; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; RECEPTOR SUBTYPE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; RECEPTOR AFFINITY;

ANIMALS; BINDING, COMPETITIVE; BRAIN; MALE; MOLECULAR STRUCTURE; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; PYRIMIDINES; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, PURINERGIC P1; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 0030004579     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950746l     Document Type: Article

References (36)

1. 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.
2. (a) Muller, C. E.; Scior, T. Adenosine receptors and their modulators. Pharm. Acta Helv. 1993, 68, 77-111.
3. 2A adenosine receptor antagonists. Curr. Med. Chem. 1995, 2, 707-722.
4. 2 receptors: structure function relationships. Med. Res. Rev. 1992, 12, 423-471.
5. 3 adenosine receptors. J. Med. Chem. 1994, 37, 3373-3382.
6. 1-selective adenosine antagonist 8-cyclopentyl-1,3-dipropyl-xanthine to rat brain membranes. Naunyn-Schmiedeberg's Arch. Pharmacol. 1987, 335, 59-63.
7. 2 antagonists. J. Med. Chem. 1992, 35, 2342-2345.
8. 2A adenosine receptor antagonists. Eur. J. Med. Chem. 1996, in press.
9. 2-selective antagonists. J. Med. Chem. 1993, 36, 1333-1342.
10. 2 receptor antagonist. Eur. J. Pharmacol. 1994, 267, 330-341.
11. 2-adenosine antagonist in vitro and in vivo. FEBS Lett. 1993, 323, 141-144.
12. 2 adenosine receptor antagonist in vivo. J. Pharmacol Exp. Ther. 1993, 267, 1304-1310.
13. 2A receptor antagonist with anticataleptic activity. Eur. J. Pharmacol. 1994, 256, 263-268.
14. 2 antagonist, (E)-1,3-dipropyl-8-(3,4-dimethoxystyryl)-7-methyl-xanthine. J. Med. Chem. 1993, 36, 3731-3733.
15. Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C.; Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L. Structure-activity profile of a series of novel triazolo-quinazoline adenosine antagonists. J. Med. Chem. 1988, 31, 1014-1020.
16. Sarges, R.; Howard, H. R.; Browne, R. G.; Lebel, L. A.; Seymour, P. A.; Koe, B. K. 4-Amino[1,2,4]triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid on set antidepressants. J. Med. Chem. 1990, 33, 2240-2254.
17. 2 adenosine receptor antagonists. Eur. J. Med. Chem. 1993, 28, 569-577.
18. 2 adenosine receptor antagonist 8FB-PTP, an 8-substituted pyrazolo-triazolo-pyrimidine, on in vitro functional models. Br. J. Pharmacol. 1994, 112, 659-665.
19. 2A adenosine receptor antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 2539-2544.
20. Topliss, J. G. Utilization of operational schemes for analog synthesis in drug design. J. Med. Chem. 1972, 15, 1006-1015.
21. 2A adenosine receptor antagonist. J Pharmacol. Exp. Ther. 1996, in press.
22. Seidlova, V.; Vejdelek, Z. J.; Rajsner, M.; Jirkovsky, I.; Protiva, M. Neurotropic and psychotic substances. XXXVI. Cycloalkylhydrazines and aralkylhydrazines. Cesk. Farm. 1969, 18, 190-197.
23. Bruzzese, T.; Casadio, S.; Coppi, G.; Marazzi-Uberti, E. Synthesis and pharmacological screening of aminoalkyl-hydrazines, J. Pharm. Sci. 1965, 7, 1056-1057.
24. Cheng, C. C.; Robins, R. K. Potential purine antagonists. VI. Synthesis of 1-aryl-4-substituted pyrazolo[3,4-d]pyridines. J. Org. Chem. 1956, 21, 1240-125.
25. Vicentini, C. B.; Veronese, C. A.; Guccione, S.; Guarneri, M.; Manfrini, M.; Giori, P. An efficient procedure for the synthesis of pyrazolo[3,4-d][1,31]thiazin-4-ones. Heterocycles 1993, 36, 2291-2301.
26. Jones, G. Azole derivatives as adenosine antagonist. WO 9414812, 1994.
27. 2A selective adenosine receptor antagonist. Br. J. Pharmacol. 1995, 115, 1096-1102.
28. 2A adenosine antagonist SCH 58261 in the rat and rabbit. Proceeding of British Pharmacology Society, Brighton, Dec. 12-15, 1995; p 152.
29. 2A adenosine receptors on the sleep-waking cycle in rats. Submitted for publication.
30. 2A adenosine receptor antagonist, to rat striatal membranes. Br. J. Pharmacol. 1996, in press.
31. 2 receptor interactions in the central nervous system. Drug Dev. Res. 1993, 28, 374-380.
32. Freedholm, B. B. Adenosine, adenosine receptors and the actions of caffeine. Pharmacol. Toxicol. 1995, 76, 93-101.
33. 3H]phenylxanthine. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 5547-5551
34. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
35. 50) of an enzymatic reaction Biochem. Pharmacol. 1973, 22, 3099-3108.
36. Born, G. V. R.; Cross, M. J. The aggregation of blood platelets. J. Physiol. 1963, 168, 178-195.