Chiral resolution and stereospecificity of 6-phenyl-4-phenylethynyl- 1,4-dihydropyridines as selective A3 adenosine receptor antagonists

Journal of Medicinal Chemistry

Volumn 42, Issue 16, 1999, Pages 3055-3065

  Jiang, Ji Long ^a   Li, An Hu ^a   Jang, Soo Yeon ^a   Chang, Louis ^a   Melman, Neli ^a   Moro, Stefano ^a   Ji, Xiao Duo ^a   Lobkovsky, Emil B ^b   Clardy, Jon C ^b   Jacobson, Kenneth A ^a  

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

^b Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 PHENYL 4 PHENYLETHYNYL 1,4 DIHYDROPYRIDINE DERIVATIVE; ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTALLIZATION; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING; STEREOSPECIFICITY; X RAY CRYSTALLOGRAPHY;

ANIMALS; BRAIN; CELL LINE; DIHYDROPYRIDINES; HUMANS; MODELS, MOLECULAR; PROTEIN CONFORMATION; RADIOLIGAND ASSAY; RATS; RECEPTOR, ADENOSINE A3; RECEPTORS, PURINERGIC P1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033549885     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980688e     Document Type: Article

References (38)

1. 3 receptors. J. Med. Chem. 1996, 39, 2980-2989.
2. 3 receptor ligands. II. Structure affinity profile of a series of isoquinoline and quinazolinecompounds. J. Med. Chem. 1998, 41, 3994-4000.
3. 3 adenosine receptor antagonists. J. Med. Chem. 1997, 40, 2596-2608.
4. Karton, Y.; Jiang, J. L.; Ji, X. D.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. Synthesis and biological-activities of flavonoid derivatives as as adenosine receptor antagonists. J. Med. Chem. 1996, 39, 2293-2301.
5. 3 receptor subtypes. J. Med. Chem. 1998, 41, 2835-2841.
6. 3 adenosine receptor antagonists. Drug Devel. Res. 1996, 37, 131.
7. 3 adenosine receptor antagonists. J. Med. Chem. 1998, 41, 3186-3201.
8. 3 receptors in mast-cells. Trends Pharmacol. Sci. 1994, 15, 13-14.
9. 3 receptor stimulation inhibits migration of human eosinophils. J. Leukocyte Biol. 1997, 62, 465-468.
10. 3 receptor stimulation and cerebral ischemia. Eur. J. Pharmacol. 1994, 263, 59-67.
11. 3 adenosine receptors: Novel ligands and paradoxical effects. Trends Pharmacol. Sci. 1998, 19, 184-191.
12. 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.
13. Coburn, R. A.; Wierzba, M.; Suto, M. J.; Solo, A. J.; Triggle, A. M.; Triggle, D. J. 1,4-Dihydropyridine antagonist activities at the calcium channel: a quantitative structure-activity relationship approach. J. Med. Chem. 1988, 31, 2103-2107.
14. Wong, W. C.; Chiu, G.; Wetzel, J. M.; Marzabadi, M. R.; Nagarathnam, D.; Wang, D.; Fang, J.; Miao, S. W.; Hong, X.; Forray, C.; Vaysse, P. J.; Branchek, T. A.; Gluchowski, C.; Tang, R.; Lepor, H. Identification of a dihydropyridine as a potent α1a adrenoceptor-selective antagonist that inhibits phenylephrine-induced contraction of the human prostate. J. Med. Chem. 1998, 41, 2643-2650.
15. 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.
16. 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.
17. Goldmann, S.; Stoltefuss, J. 1,4-Dihydropyridines: Effects of Chirality and Conformation on the Calcium Antagonist and Calcium Agonist Activities. Angew. Chem., Int. Ed. Engl. 1991, 30, 1559-1578.
18. 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.
19. Rovnyak, G. C.; Kimball, S. D.; Beyer, B.; Cucinotta, G.; DiMarco, J. D.; Gougoutas, J.; Hedberg, A.; Malley, M.; McCarthy, J. P.; Zhang, R.; Moreland, S. Calcium entry blockers and activators: conformational and structural determinants of dihydropyrimidine calcium channel modulators. J. Med. Chem. 1995, 38, 119-129.
20. Wenzel, T. J.; Bettes, T. C.; Sadlowski, J. E.; Sievers, R. E. New Binuclear Lanthanide NMR Shift Reagents Effective for Aromatic Compounds. J. Am. Chem. Soc. 1980, 102, 5903-5904.
21. Sheldrick, G. M. SHELX-86. A Computer Program for Crystal Structure Determination; University of Gottingen: Gottingen, 1986.
22. Sheldrick, G. M. SHELX-93. Program for the Refinement of Crystal Structures; University of Gottingen: Gottingen, 1993.
23. Suemune, H.; Harabe, T.; Sakai, K. Syntheses of Unsaturated Trihydroxy C-18 Fatty Acids Isolated from Rice Plants Suffering from Rice Blast Disease. Chem. Pharm. Bull. 1988, 36, 3632-3637.
24. 6-phenylisopropyladenosine. Naunyn-Schmiedeberg's Arch. Pharmacol. 1980, 313, 179-187.
25. 2 receptors in rat brain tissue. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
26. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 978-982.
27. 3-adenosine receptors. Drug Devel. Res. 1994, 33, 51-59.
28. 3 adenosine receptor antagonists: structural homology and receptor docking. J. Chem. Inf. Comput. Sci. 1998, in press.
29. 50) of an enzyme reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
30. 3 adenosine receptor antagonists. J. Med. Chem. 1999, 42, 706-721.
31. The program SYBYL 6.3 is available from TRIPOS Associates, St. Louis, MO; 1993.
32. Dewar, M. J. S. E.; Zoebisch, G.; Healy, E. F. AM1: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
33. MOPAC 6.0 is available from Quantum Chemistry Program Exchange.
34. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel-An Integrated Software System for Modeling Organic and Bioorganic Molecules using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-450.
35. Kyte, J.; Doolittle, R. F. A simple method for displaying the hydrophobic character of a protein. J. Mol. Biol. 1982, 157, 105-132.
36. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. An all-atom force field for simulation of protein and nucleic acids. J. Comput. Chem. 1986, 7, 230-252.
37. 1 receptor: molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites. J. Med. Chem. 1998, 41, 1456-1466.
38. 3 Adenosine Receptors. Bioconjugate Chem. 1999, 10, 667-677.