Tetrahydrobenzothiophenone derivatives as a novel class of adenosine receptor antagonists

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 398-406

  Michiel Van Rhee, A ^a   Siddiqi, Suhaib M ^a   Melman, Neli ^a   Shi, Dan ^a   Padgett, William L ^a   Daly, John W ^a   Jacobson, Kenneth A ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

2 [4 (2 CARBOXYETHYL)PHENETHYLAMINO]ADENOSINE 5' (N ETHYLCARBOXAMIDE); 3 (BENZYLTHIO) 4,5,6,7 TETRAHYDRO 4 OXOBENZO[C]THIOPHENE 1 CARBOXYLIC ACID ETHYL ESTER; 3 (ETHYLTHIO) 4,5,6,7 TETRAHYDRO 6,6 DIMETHYL 4 OXOBENZO[C]THIOPHENE 1 CARBOXYLIC ACID ETHYL ESTER; 3 (ETHYLTHIO) 4,5,6,7 TETRAHYDRO 6,6 DIMETHYL 4 OXOBENZO[C]THIOPHENE 1 CARBOXYLIC ACID METHYL ESTER; 3 (SEC BUTYLTHIO) 4,5,6,7 TETRAHYDRO 6,6 DIMETHYL 4 OXOBENZO[C]THIOPHENE 1 CARBOXYLIC ACID ETHYL ESTER; 4 [2 [7 AMINO 2 (2 FURYL) 1,2,4 TRIAZOLO[2,3 A][1,3,5]TRIAZIN 5 YLAMINO]ETHYL]PHENOL; 4 AMINO 8 CHLORO 1 PHENYL 1,2,4 TRIAZOLO[4,3 A]QUINOXALINE; 4,5 DIHYDRO 1 (METHYLTHIO)BENZO[C]THIOPHENE 3 CARBOXYLIC ACID HYDRAZIDE; 5 AMINO 2 (2 FURYL) 7 (2 PHENYLETHYL)PYRAZOLO[4,3 E][1,2,4]TRIAZOLO[1,5 C]PYRIMIDINE; 9 CHLORO 2 (2 FURYL) 5,6 DIHYDRO 5 IMINO 1,2,4 TRIAZOLO[2,3 C]QUINAZOLINE; ADENOSINE A1 RECEPTOR; ADENOSINE A2 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; ADENYLATE CYCLASE; CAFFEINE; CYCLOHEXYLADENOSINE; PHENYLISOPROPYLADENOSINE; RADIOLIGAND; UNCLASSIFIED DRUG;

ADIPOCYTE MEMBRANE; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; LIGAND BINDING; LOCOMOTION; MALE; MOLECULAR MODEL; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; PHEOCHROMOCYTOMA CELL; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; HUMANS; MALE; MICE; MODELS, MOLECULAR; MOTOR ACTIVITY; RATS; RECEPTORS, PURINERGIC P1; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 13344284649     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9504823     Document Type: Article

References (40)

1. Olsson, R. A.; Pearson, J. D. Cardiovascular purinoceptors. Pharmacol. Rev. 1990, 3, 761-845.
2. 6-cyclohexyladenosine in the isolated perfused rat kidney. J. Pharmacol. Exp. Ther. 1987, 240, 911-915.
3. Londos, C.; Cooper, D. M.; Wolff, J. Subclasses of external adenosine receptors. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 2551-2554.
4. 1 subtype adenosine receptor on pancreatic insulin-secreting cells. Eur. J. Pharmacol. 1987, 136, 109-112.
5. Fredholm, B. B.; Dunwiddie, T. V. How does adenosine inhibit transmitter release? Trends Pharmacol. Sci. 1988, 9, 130-134.
6. 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.
7. von Lubitz, D. K. J. E.; Jacobson, K. A. Behavioral effects of adenosine receptor stimulation. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Bellardinelli, L., Pelleg, A., Eds.; Kluwer: Norwell, 1995; pp 489-498.
8. Stiles, G. L. Adenosine receptors. J. Biol. Chem. 1992, 267, 6451-6454.
9. Jacobson, M. A. Cloning and expression of human adenosine receptor subtypes. In Adenosine and Adenine Nucleotides: From Molecular Biology to Integrative Physiology; Bellardinelli, L., Pelleg, A., Eds.; Kluwer: Norwell, 1995; pp 5-13.
10. 3 adenosine receptors. J. Med. Chem. 1994, 37, 3373-3382.
11. 2-adenosine receptors. Biochem. Pharmacol. 1988, 37, 655-664.
12. 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 triazoloquinazoline adenosine antagonists. J. Med. Chem. 1988, 31, 1014-1020.
13. 1-Adenosine Receptor. J. Med. Chem. 1991, 34, 2877-2882.
14. 2a adenosine receptor antagonists. Bioorg. Med. Chem. Lett. 1994, 4, 2539-2544.
15. 2a selective adenosine antagonist. Br. J. Pharmacol. 1994, abstract.
16. 2-adenosine receptors. Pharmazie 1994, 49, 878-880.
17. 1 adenosine receptor in the anaesthetised pig: pharmacological and therapeutic implications. Cardiovasc. Res. 1994, 28, 621-628.
18. 2a adenosine binding activities of some 1-aryl-1,4-dihydro-3-methyl-[1]benzopyrano[2,3-c]pyrazol-4-ones, 1-aryl-4,9-dihydro-3-methyl-1H-pyrazolo-[3,4-b]quinolin-4-ones, and 1-aryl-1H-imidazo-[4,5-b]quinoxalines. J. Med. Chem. 1995, 38, 1330-1336.
19. 1-purinergic (adenosine) receptor in FRTL-5 thyroid cells. Biochem. Biophys. Res. Commun. 1994, 203, 1488-1495.
20. 1 receptor ligand isolated from Salvia Militorrhiza bunge (Danshen). Tetrahedron Lett. 1991, 32, 2061-2064.
21. 3-adenosine receptors. J. Med. Chem. 1994, 37, 636-646.
22. 3 adenosine receptors. J. Med. Chem. 1994, 37, 3614-3621.
23. 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.
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. 2-adenosine receptors coupled to adenylate cyclase. Biochem. Pharmacol. 1992, 43, 1089-1093.
28. 2-adenosine antagonist in vitro and in vivo. FEBS Lett. 1993, 323, 141-144.
29. Nikodijevic', O.; Jacobson, K. A.; Daly, J. W. Locomotor activity in mice during chronic treatment with caffeine and withdrawal. Pharmacol. Biochem. Behav. 1993, 44, 199-216.
30. 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.
31. Francis, J. E.; Cash, W. D.; Psychoyos, S.; Ghai, G.; Wenk, P.; Friedmann, R. C., Atkins, C.; Warren, V.; Furness, P.; Hyun, J. L.; Stone, G. A.; Desai, M.; Williams, M. Structure-activity profile of a series of novel triazoloquinazoline adenosine antagonists. J. Med. Chem. 1988, 31, 1014-1020.
32. 1 receptor, based on steric, electrostatic, and hydrophobic properties. J. Med. Chem. 1990, 33, 1708-1713.
33. van Galen, P. J. M.; Nissen, P.; van Wijngaarden, I.; IJzerman, A. P.; Soudijn, W. 1H-Imidazo[4,5-c]quinolin-4-amines: novel non-xanthine adenosine antagonists. J. Med. Chem. 1991, 34, 1202-1206.
34. 1 receptor ligands - A test-case for Distributed Multipole Analysis in medicinal chemistry. J. Comput.-Aided Mol Des. 1995, 9, 44-54.
35. 3 adenosine receptor agonists. Bioorg. Med. Chem. 1995, 3, 1331-1343.
36. 3 adenosine receptor. Mol. Pharmacol. 1994, 45, 1101-1111
37. 2a adenosine receptors from rat striatum and rat pheochromocytoma PC12 cells: characterization with radioligand binding and by activation of adenylate cyclase. Mol. Pharmacol. 1992, 41, 352-359.
38. 50) of an enzyme reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
39. 3-adenosine receptors. Drug Dev. Res. 1994, 33, 51-59.
40. Ji, X. D.; Melman, N.; Jacobson, K. A. Interactions of flavonoids and other phytochemicals with adenosine receptors. J Med. Chem 1996, in press.