Interaction of 1,4-dihydropyridine and pyridine derivatives with adenosine receptors: Selectivity for A3 receptors

Journal of Medicinal Chemistry

Volumn 39, Issue 15, 1996, Pages 2980-2989

  Van Rhee, A Michiel ^a   Jiang, Ji Long ^a   Melman, Neli ^a   Olah, Mark E ^b   Stiles, Gary L ^b   Jacobson, Kenneth A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 DIHYDRO 2 METHYL 6 PHENYL 4 (2 PHENYLVINYL) 3,5 PYRIDINEDICARBOXYLIC ACID DIETHYL ESTER; 1,4 DIHYDRO 2,6 DIMETHYL 5 NITRO 4 [2 (TRIFLUOROMETHYL)PHENYL] 3 PYRIDINECARBOXYLIC ACID METHYL ESTER; 1,4 DIHYDROPYRIDINE; 1,4 DIHYDROPYRIDINE DERIVATIVE; 2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); ADENOSINE A3 RECEPTOR; ADENOSINE DERIVATIVE; ADENOSINE RECEPTOR BLOCKING AGENT; CALCIUM CHANNEL BLOCKING AGENT; IODINE 125; ISRADIPINE; MRS 1097; NICARDIPINE; NIFEDIPINE; NIGULDIPINE; NIMODIPINE; NITRENDIPINE; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BRAIN MEMBRANE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LIGAND BINDING; NONHUMAN; RAT; RECEPTOR BLOCKING; STRUCTURE ACTIVITY RELATION;

ADENYLATE CYCLASE; ANIMALS; CALCIUM CHANNEL BLOCKERS; CALCIUM CHANNELS; CELL MEMBRANE; CEREBRAL CORTEX; CHO CELLS; CRICETINAE; DIHYDROPYRIDINES; ENZYME INHIBITORS; GUINEA PIGS; HUMANS; ISRADIPINE; MOLECULAR STRUCTURE; PYRIDINES; RATS; RECEPTORS, PURINERGIC P1; RECOMBINANT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0029977331     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9600205     Document Type: Article

References (43)

1. Triggle, D. J. Drugs acting on ion channels and membranes. In Comprehensive Medicinal Chemistry; Emmett, J. C., Ed.; Pergamon Press: London, 1985; Vol. 3, pp 1047-1099.
2. Borchard, U. Calcium antagonists in comparison: view of the pharmacologist. J. Cardiovasc. Pharmacol. 1994, 24, Suppl 2, S85-91.
3. Coburn, R. A.; Wierzba, M.; Suto, M. J.; Solo, A. J.; Triggle, A. M.; Triggle DJ. 1,4-Dihydropyridine antagonist activities at the calcium channel: a quantitative structure-activity relationship approach. J. Med. Chem. 1988, 31, 2103-2107.
4. 2+ channel antagonist niguldipine. J. Med. Chem. 1995, 38, 1579-1581.
5. Sunkel, C. E.; de Casa-Juana, M. F.; Santos, L.; Gomez, M. M.; Villarroya, M.; Gonzalez-Morales, M. A.; Priego, J. G.; Ortega, M. P. 4-Alkyl-1,4-dihydropyridines derivatives as specific PAF-acether antagonists. J. Med. Chem. 1990, 33, 3205-3210.
6. Lopez, M. G.; Fonteriz, R. I.; Gandia, L.; de la Fuente, M.; Villarroya, M.; Garcia-Sancho, J.; Garcia, A. G. The nicotinic acetylcholine receptor of the bovine chromaffin cell, a new target for dihydropyridines. Eur. J. Pharmacol. 1993, 247, 199-207.
7. Hu, P. S.; Lindgren, E.; Jacobson, K. A.; Fredholm, B. B. Interaction of dihydropyridine calcium channel agonists and antagonists with adenosine receptors. Pharmacol. Toxicol. 1987, 61, 121-125.
8. Ismail, N. A.; Shaheen, A. A.; El-Sawalhi, M. M.; Megahed, Y. M. Effect of calcium channel antagonists in modifying the inhibitory influence of adenosine on insulin secretion. Arzneim.-Forsch.lDrug Res. 1995, 45, 865-868.
9. 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.
10. 2-adenosine receptors. Biochem. Pharmacol. 1988, 37, 655-64.
11. Siddiqi, S. M.; Ji, X. D.; Melman, N.; Olah, M. E.; Jain, R.; Evans, P.; Glashofer, M.; Padgett, W. L.; Cohen, L. A.; Daly, J. W.; Stiles, G. L.; Jacobson, K. A. A survey of non-xanthine derivatives as adenosine receptor ligands. Nucleosides Nucleotides 1996, 15, 693-718.
12. van Rhee, A. M.; Siddiqi, S. M.; Melman, N.; Shi, D.; Padgett, 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.
13. Ji, X. D.; Melman, N.; Jacobson, K. A. Interactions of flavonoids and other phytochemicals with adenosine receptors. J. Med. Chem. 1998, 39, 781-788.
14. 3 adenosine receptors: design of selective ligands and therapeutic prospects. Drugs Future 1995, 20, 689-699.
15. 3 receptors in mast-cells. Trends Pharmacol. Sci. 1994, 15, 13-14.
16. 3 receptor stimulation and cerebral ischemia. Eur. J. Pharmacol. 1994, 263, 59-67.
17. MacKenzie, W. M.; Hoskin, D. W.; Blay, J. Adenosine inhibits the adhesion of anti-CDS-activated killer lymphocytes to adenocarcinoma cells through an AS receptor. Cancer Res. 1994, 54, 3521-3526.
18. 3 receptor agonists. Biochem. Biophys. Res. Commun. 1996, 219, 904-910.
19. 3-adenosine receptors: Mediation of behavioral depressant effects. FEBS Lett. 1993, 336, 57-60.
20. 3 receptors, J. Med. Chem. 1994, 37, 3614-3621.
21. 3 adenosine receptors. J. Med. Chem. 1994, 37, 3373-3382.
22. 3 adenosine receptor. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 7432-7436.
23. 3 adenosine receptor. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 10365-10369.
24. 3 adenosine receptor with widespread tissue distribution. Mol. Pharmacol. 1993, 44, 524-532.
25. 3-adenosine receptors. Drug Dev. Res. 1994, 33, 51-59.
26. Stout, D. M.; Myers, A. I. Recent advances in the chemistry of dihydropyridines. Chem. Rev. 1982, 82, 223-243.
27. Singer, A.; McElvain, S. M. 2,6-Dimethylpyridine. Org. Synth. 1934, 14, 30-33.
28. Rathke, M. W.; Deitch, J. The reaction of lithium ester enolates with acid chlorides. A convenient procedure for the preparation of β-keto esters. Tetrahedron Lett. 1971, 31, 2953-2956.
29. Braude, E. A.; Hannah, J.; Linstead, R. Hydrogen Transfer. Part XVI. Dihydrides of nitrogenous heterocycles as hydrogen donors. J. Chem. Soc. 1960, 3249-3257.
30. 6-phenylisopropyladenosine. Naunyn-Schmiedeberg's Arch. Pharmacol. 1980, 373, 179-187.
31. 2 receptors in rat brain tissue. J. Pharmacol. Exp. Ther. 1989, 257, 888-893.
32. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 978-982.
33. Triggle, D. J. 1,4-Dihydropyridine activators and antagonists: structural and functional distinctions. Trends Pharmacol. Sci. 1989, 10, 507-511.
34. Meyer, H.; Bossert, F.; Wehinger, E.; Stoepel, K.; Vater, W. Synthesis and comparative pharmacological studies of 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylates with non-identical ester functions. Arzneim.-Forsch. 1981, 31, 407-9.
35. Höllt, V.; Kouba, M.; Dietel, M.; Vogt, G. Stereoisomers of calcium antagonists which differ markedly in their potencies as calcium blockers are equally effective in modulating drug transport by P-glycoprotein. Biochem. Pharmacol. 1992, 43, 2601-2608.
36. 3H]isradipine binding to L-type calcium channels by the optical isomers of isoflurane. Lack of stereospecificity. Anesthesiology 1994, 81, 124-128.
37. 2+ antagonist receptor sites on human red blood cell membranes. Eur. J. Pharmacol. 1985, 108, 329-330.
38. Sweetnam, P. M.; Caldwell, L.; Lancaster, J.; Bauer, C.; McMillan, B.; Kinnier, W. J.; Price, C. H. The role of receptor binding in drug discovery. J. Nat. Prod. 1993, 56, 441-455.
39. Gerlach, M.; Riederer, P.; Youdim, M. Neuroprotective therapeutic strategies: Comparison of experimental and clinical results. Biochem. Pharmacol. 1995, 50, 1-16.
40. Gessner, W.; Brossi, A.; Shen, R.-S.; Abell, C. W. Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine. J. Med. Chem. 1985, 28, 311-317.
41. 50) of an enzyme reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
42. Marangos, P. J.; Patel, J.; Clark-Rosenberg, R.; Martino, A. M. Nitrobenzylthio-inosine binding as a probe for the study of adenosine uptake sites in brain. J. Neurochem. 1982, 39, 184-191.
43. 3H]nitrobenzylthioinosine binding to the adenosine transporter in human brain. Eur. J. Pharmacol. 1993, 238, 131-133.