Novel N6-(substituted-phenylcarbamoyl)adenosine-5′-uronamides as potent agonists for A3 adenosine receptors

Journal of Medicinal Chemistry

Volumn 39, Issue 3, 1996, Pages 802-806

  Baraldi, Pier Giovanni ^a   Cacciari, Barbara ^a   Spalluto, Giampiero ^a   Ji, Xiao Duo ^b   Olah, Mark E ^d   Stiles, Gary ^d   Dionisotti, Silvio ^c   Zocchi, Cristina ^c   Ongini, Ennio ^c   Jacobson, Kenneth A ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c Schering Plough   (Italy)

^d DUKE UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); 6 N [(2 CHLOROPHENYL)CARBAMOYL]ADENOSINE 5' ETHYLURONAMIDE; 6 N [(3 CHLOROPHENYL)CARBAMOYL]ADENOSINE 5' ETHYLURONAMIDE; 6 N [(4 METHOXYPHENYL)CARBAMOYL]ADENOSINE 5' ETHYLURONAMIDE; ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR STIMULATING AGENT; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG; ADENOSINE RECEPTOR; ADENYLATE CYCLASE; AMIDE;

ANIMAL CELL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BRAIN PROTECTION; CHO CELL; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; MALE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; ANIMAL; BRAIN; DRUG EFFECT; DRUG POTENTIATION; HAMSTER; METABOLISM; SPRAGUE DAWLEY RAT;

ADENYLATE CYCLASE; AMIDES; ANIMALS; BRAIN; CHO CELLS; CRICETINAE; MALE; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, PURINERGIC P1;

EID: 0029664987     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950518r     Document Type: Article

References (42)

1. Jacobson, K. A.; van Galen, P. J. M.; Williams, M. Perspective Adenosine Receptors: pharmacology, structure-activity relationship and therapeutic potential. J. Med. Chem. 1992, 35, 407-422.
2. 1 adenosine receptors. EMBO J. 1981, 10, 1677-1682.
3. 2 receptor with physiological constitutive activity. Biochem. Biophys. Res. Commun. 1990, 173, 1169-1178.
4. 2-adenosine receptor subtype. Mol. Endocrinol. 1992, 6, 384-393.
5. 3 adenosine receptor. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7432-7436.
6. Londos, C.; Cooper, D. M.; Wolff, J. Subclasses of external adenosine receptors. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2551-2554.
7. Hamprecht, B.; Van Calker, D. Nomenclature of adenosine receptors. Trends Pharmacol. Sci. 1985, 6, 153-154.
8. 2 receptors. Can. J. Physiol. Pharmacol. 1987, 65, 365-376.
9. 3AR is the unique adenosine receptor which facilitates release of allergic mediators in mast cells. J. Biol. Chem. 1993, 268, 6871-6890.
10. 3 receptor agonists activate phospholipase C in rat brain via a G-protein. Soc. Neurosci. 1995, submitted.
11. 3H] phenylxanthine. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 5547-5551.
12. 2 adenosine receptors. J. Med. Chem. 1986, 29, 1683-1689.
13. 6-sulfoalkyl derivatives of adenosine. Water soluble and peripherally selective adenosine agonists. J. Med. Chem. 1992, 35, 4143-4149.
14. 1-adenosine receptors. J. Med. Chem. 1988, 31, 613-617.
15. 1 receptors. J. Med. Chem. 1988, 31, 745-751.
16. 2 adenosine receptors. Biochem. Pharmacol. 1988, 37, 3653-3661.
17. 2 adenosine receptors. J. Med. Chem. 1992, 35, 2363-2368.
18. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
19. 2 antagonists. J. Med. Chem. 1992, 35, 2342-2345.
20. 2-selective adenosine antagonists. J. Med. Chem. 1993, 36, 1333-1342.
21. 2A adenosine receptor antagonist. Bioorg. Med. Chem. Lett. 1994, 4, 2539-2544.
22. 2A adenosine receptor antagonists. Curr. Med. Chem. 1995, 2, 707-722.
23. 2 receptors in the ventral striopallidal system-implications for the treatment of schizophrenia. Neuroscience 1994, 63, 765-773.
24. 1-antagonists for treatment of cognitive deficits. Nucleosides Nucleotides 1991, 10, 1067-1076.
25. 6-(2,2-diphenylethy)adenosine, a novel adenosine receptor agonist with antipsychotic-like activity. J. Med. Chem. 1987, 30, 1709-1711.
26. Jacobson, K. A.; Trivedi, B. K.; Churchill, P. C.; Williams, M. Novel therapeutics acting via purine receptors. Biochem. Pharmacol. 1991, 41, 1399-1410.
27. 3 adenosine receptors. J. Wed. Chem. 1994, 37, 3373-3382.
28. 3 receptors: Structure activity relationship and molecular modeling. ACS 206th National Meeting, Chicago, IL, August 1993, Abstract MEDI217.
29. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 1101-1111.
30. 3-adenosine receptors: Mediation of behavioral depressant effects. FEBS Lett. 1993, 336, 57-60.
31. 3-selective adenosine agonists. J. Med. Chem. 1994, 37, 636-646.
32. 3 adenosine receptors. J. Med. Chem. 1994, 37, 3614-3621.
33. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 978-982.
34. 3 adenosine receptor. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 10365-10369.
35. 3 adenosine receptor with widespread tissue distribution. Mol. Pharmacol. 1993, 44, 524-532.
36. 3 receptor stimulation and cerebral ischemia. Eur. J. Pharmacol. 1994, 263, 59-67.
37. 3 receptor stimulation on seizures in mice. Eur. J. Pharmacol. 1995, 275, 23-29.
38. 3 receptor can mediate preconditioning's protection in isolated rabbit hearts. Cardiovasc. Res. 1994, 28, 1007-1061.
39. 3 receptors in mast-cells. Trends Pharmacol. Sci. 1994, 75, 13-14.
40. Kurita, K.; Iwakura, Y. Trichloromethyl-Chloroformate as a phosgene equivalent: 3-isocyanatopropanoylchloride. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, pp 715-718.
41. 3-adenosine receptors: structure activity relationship of 1,3-dialkylxanthine-7-riboside derivatives. J. Med. Chem. 1994, 37, 4020-4030.
42. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.