2-Alkenyl and 2-alkyl derivatives of adenosine and adenosine-5'-N- ethyluronamide: Different affinity and selectivity of E- and Z-diastereomers at A(2A) adenosine receptors

Journal of Medicinal Chemistry

Volumn 39, Issue 21, 1996, Pages 4211-4217

  Vittori, Sauro ^a   Camaioni, Emidio ^a   Di Francesco, Emanuela ^a   Volpini, Rosaria ^a   Monopoli, Angela ^b   Dionisotti, Silvio ^b   Ongini, Ennio ^b   Cristalli, Gloria ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b Schering Plough Research Institute   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A2 RECEPTOR; ADENOSINE DERIVATIVE; RECEPTOR SUBTYPE;

ANIMAL TISSUE; ARTICLE; BRAIN MEMBRANE; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; NONHUMAN; RAT; RECEPTOR AFFINITY; THROMBOCYTE AGGREGATION INHIBITION;

ADENOSINE; ADENOSINE-5'-(N-ETHYLCARBOXAMIDE); ALKYLATION; ANIMALS; MALE; PLATELET AGGREGATION; RATS; RATS, WISTAR; RECEPTORS, PURINERGIC P1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029819281     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960376g     Document Type: Article

References (49)

1. Fredholm, 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 (2), 143-213.
2. Palmer, T. M.; Stiles, G. L. Adenosine receptors. Neuropharmacology 1995, 34 (7), 683-694.
3. Olah, M. E.; Stiles, G. L. Adenosine receptor subtypes: characterization and therapeutic regulation. Annu. Rev. Pharmacol. Toxicol. 1995, 35, 581-606.
4. 2 receptor with physiological constitutive activity. Biochem. Biophys. Res. Commun. 1990, 173, 1169-1178.
5. 2 adenosine receptor agonists on cardiovascular tissues. Naunyn-Schmiedeberg's Arch. Pharmacol. 1993, 348, 108-112.
6. Dionisotti, S.; Zocchi, C.; Varani, K.; Borea, P. A.; Ongini, E. Effects of adenosine derivatives on human and rabbit platelet aggregation. Correlation of adenosine receptor affinities and antiaggregatory activity. Naunyn-Schmiedeberg's Arch. Pharmacol. 1992, 346, 673-676.
7. Stone, T. W.; Collis, M. G.; Williams, M.; Miller, L. P.; Karasawa, A.; Hillaire-Buys, D. Adenosine: some therapeutic applications and prospects. In Pharmacological sciences: perspectives for research and therapy in the late 1990s; Cuello, A. C., Collier, B., Eds.; Birkhauser Verlag: Basel, Switzerland, 1995; pp 303-309.
8. 2 adenosine receptor subtype. Mol. Endocrinol. 1992, 6, 384-393.
9. 2 dopamine receptors in rat striatum. Mol. Brain Res. 1992, 14, 186-195.
10. 2 receptors regulate the gene expression of striatopallidal and striatonigral neurons. J. Neurosci. 1993, 13, 1080-1087.
11. Schiffmann, S. N.; Jacobs, O.; Vanderhaeghen, J.-J. The striatal restricted adenosine A2 receptor 4. J. Neurosci. 1991, 57, 1062-1067.
12. 2 receptors in the neurostriatum. Brain Res. 1992, 594, 124-130.
13. 2 receptors in the ventral striopallidal system. Implications for the treatment of schizophrenia. Neuroscience 1994, 63, 765-773.
14. (a) Erfurth, A. Adenosine and neuropsychiatriac disordes. CNS Drugs 1994, 2 (3), 184-190.
15. (b) Wite, T. D.; Ribeiro, J. A.; Edwards, F. A.; Fredholm, B. B.; Phillis, J. W. Role of purines in the central nervous system. In Pharmacological sciences: perspectives for research and therapy in the late 1990s; Cuello, A. C., Collier, B., Eds.; Birkhauser Verlag: Basel, Switzerland, 1995; pp 295-302.
16. 2 receptors: Structure-function relationships. Med. Res. Rev. 1992, 12, 423-471.
17. 1 adenosine receptors. Naunyn-Schmiedeberg's Arch. Pharmacol. 1988, 337, 687-689.
18. (a) Ueeda, M.; Thompson, R. D.; Arroyo, L. H.; Olsson, R. A. 2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor. J. Med. Chem. 1991, 34, 1334-1339.
19. 2 adenosine receptor. J. Med. Chem. 1991, 34, 1340-1344.
20. (a) Matsuda, A.; Ueda, T. The synthesis, mutagenic and pharmacological activities of 2-carbon-substituted adenosines. Nucleosides Nucleotides 1987, 6, 85-94.
21. 2 receptors. Eur. J. Pharmacol. 1991, 196, 69-76.
22. 2 receptor agonists with potential antihypertensive effects. J. Med. Chem. 1992, 35, 241-252.
23. 2 receptor agonists with potent antihypertensive effects. J. Med. Chem. 1992, 35, 2253-2260.
24. (a) Kazunori, N.; Olsson, R. A.; Thompson, R. D.; Silvia, S. K.; Ueeda, M. 2-(N'-Alkylidenehydrazino)adenosines: potent and selective coronary vasodilators. J. Med. Chem. 1992, 35, 4557-4561.
25. (b) Kazunori, N.; Thompson, R. D.; Silvia, S. K.; Olsson, R. A. 2-(N'-Aralkylidenehydrazino)adenosines: potent and selective coronary vasodilators. J. Med. Chem. 1992, 35, 4562-4566.
26. 2A adenosine agonist properties and vasodilation activity. J. Med. Chem. 1995, 38, 3581-3585.
27. 3H]NECA in rat striatal membranes. Mol. Pharmacol. 1986, 29, 331-346.
28. 2 selective adenosine receptor agonist with preferential hypotensive activity. J. Pharmacol. Exp. Ther. 1989, 251, 47-55.
29. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
30. 2 receptor ligands. J. Med. Chem. 1990, 33, 1919-1924.
31. 2 adenosine receptors. J. Med. Chem. 1992, 35, 2363-2368.
32. 2 adenosine receptor agonist. Arzneim.-Forsch. 1994, 44 (II), 1296-1304.
33. 2A adenosine receptor agonists. Naunyn-Schmiedeberg's Arch. Pharmacol. 1994, 349 (6), 644-650.
34. (a) Belardinelli, L.; Pelleg, A. Rationale for the use of adenosine in the diagnosis and treatment of cardiac arrhythmias. In Purine in cellular signaling: targets for new drugs; Jacobson, K. A., Daly, J. V., Manganiello, V., Eds.; Springer-Verlag: New York, 1990; pp 95-99.
35. (b) Pelleg, A.; Belardinelli, L. Cardiac electrophysiology and pharmacology of adenosine: basic and clinical aspects. Cardiovasc. Res. 1993, 27, 54-61.
36. Rudolphi, K. A.; Schubert, P.; Parkinson, F. E.; Fredholm, B. B. Neuroprotective role of adenosine in cerebral ischaemia. Trends Pharmacol. Sci. 1992, 13, 439-445.
37. 2 adenosine receptor agonists with potent inhibitory activity on platelet aggregation. J. Med. Chem, 1994, 37, 1720-1726.
38. 2 adenosine receptor agonists. J. Med. Chem. 1995, 38, 1462-1472.
39. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. A convenient synthesis of ethynylarenes and diethynylarenes. Synthesis 1980, 627-630.
40. Brown, H. C.; Gupta, S. K. Hydroboration. XXXIX. 1,3,2-Benzodioxaborole (catecholborane) as a new hydroboration reagent for alkenes and alkynes. J. Am. Chem. Soc. 1975, 97, 5249-5255.
41. Nair, V.; Richardson, S. G. Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine nucleosides. Synthesis 1982, 670-672.
42. Bruns, R. F.; Daly, J. W.; Snyder, S. H. Adenosine receptors in brain membranes: binding of N6-cydohexyl-[3H]adenosine and 1,3-diethyl-8[3H]phenylxanthine. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 5547-5551.
43. Brent, D. A.; Sabatka, J. J.; Minick, D. J.; Henry, D. W. A simplified high-pressure liquid chromatography method for determining lipophilicity for structure-activity relationships. J. Med. Chem. 1983, 26, 1014-1020.
44. Zhang, H. X.; Giubé, F.; Balavoine, G. Palladium and molybdenum-catalyzed hydrostannation of alkynes. A novel access to regio- and stereodefined vinylstannanes. J. Org. Chem. 1990, 55, 1857-1867.
45. Finney, D. J. Statistical methods in biological assays, 3rd ed.; Griffin: London, 1978; pp 80-82.
46. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
47. Snedecor, G. W.; Cochran, W. G. Statistical Methods, 6th ed.; The Iowa State University Press: Ames, IA, 1967.
48. SAS Institute Inc. SAS/STAT Guide for personal computers, Version 6; SAS Institute Inc.: Cary, NC, 1987; pp 549-640.
49. Born, G. V. R.; Cross, M. J. The aggregation of blood platelets. J. Physiol. 1963, 168, 178-195.