Structure-Activity Relationships for 2-Substituted Imidazoles as α2-Adrenoceptor Antagonists

Journal of Medicinal Chemistry

Volumn 25, Issue 6, 1982, Pages 666-670

  Caroon, Joan M ^a   Clark, Robin D ^a   Kluge, Arthur F ^a   Olah, Ronald ^a   Repke, David B ^a   Unger, Stefan H ^a   Michel, Anton D ^b   Whiting, Roger L ^b  

^a Syntex Research Institute of Organic Chemistry   (United States)

^b Syntex Research Europe   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 [(1,4 BENZODIOXAN 2 YL)METHYL] 1 ETHYLIMIDAZOLE; 2 [(1,4 BENZODIOXAN 2 YL)METHYL]IMIDAZOLE DERIVATIVE; ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; ALPHA ADRENERGIC RECEPTOR BLOCKING AGENT; AMIDEFRINE MESILATE; IMIDAZOLE; NEW DRUG; PA2 VALUE; PHENTOLAMINE; PIPEROXAN; RAUWOLSCINE; UNCLASSIFIED DRUG; XYLAZINE; YOHIMBINE;

ANIMAL CELL; ARTICLE; DRUG ANALYSIS; DRUG ANTAGONISM; DRUG COMPARISON; DRUG IDENTIFICATION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SOLUBILITY; DRUG SYNTHESIS; GREAT BLOOD VESSEL; NONHUMAN; PERIPHERAL NERVOUS SYSTEM; PHARMACOKINETICS; RAT; STRUCTURE ACTIVITY RELATION;

ADRENERGIC ALPHA-ANTAGONISTS; ANIMALS; CHEMISTRY; IMIDAZOLES; MALE; MUSCLE CONTRACTION; MUSCLE, SMOOTH; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VAS DEFERENS;

EID: 0020380352     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00348a012     Document Type: Article

References (40)

1. Langer, S. Z. Biochem. Pharmacol. 1974, 23, 1793.
2. Berthelsen, S.; Pettinger, W. A. Life Sci. 1977, 21, 595.
3. Starke, K.; Langer, S. Z. Adv. Biosci. 1974, 18, 1.
4. For reviews, see (a) Melchiorre, C. Farmaco 1980, 35, 535.
5. Hoffman, B. B.; Lefkowitz, R. J. N. Engl. J. Med. 1980, 1390.
6. Rand, M. J.; Majewski, H., Medgett, I. C.; McCulloch, M. W.; Story, D. F. Circ. Res., Supplement 1980, 46, I–70.
7. Lefkowitz, R. F. Annu. Rep. Med. Chem. 1980, 15, 217.
8. Timmermans, P. B. M. W. M.; Van Zwieten, P. A. J. Auton. Pharmacol. 1981, 1, 171.
9. Langer, S. Z. Br. J. Pharmacol. 1977, 60, 481.
10. Wood, C. L.; Arnett, C. D.; Clarke, W. R.; Tsai, B. S.; Lefkowitz, R. J. Biochem. Pharmacol. 1979, 28, 1277.
11. Brogden, R. N.; Heel, R. C.; Speight, T. M.; Avery, G. S. Drugs 1977, 14, 163.
12. Wilkinson, P. R.; Raftery, E. B. Br. J. Clin. Pharmacol. 1977, 4, 289.
13. Michel, A. D.; Whiting, R. L. Br. J. Pharmacol. 1981, 74, 256P.
14. Drew, G. M. Br. J. Pharmacol. 1978, 64, 293.
15. Borowski, E.; Starke, K.; Ehrl, H.; Endo, T. Neuroscience 1977, 2, 285.
16. Weitzell, R.; Tanaka, T.; Starke, K. Naunyn-Schmiedegerg's Arch. Pharmacol. 1979, 308, 127.
17. Timmermans, P. B. W. M.; VanZweiten, P. A. Naunyn-Schmiedeberg's Arch. Pharmacol. 1980, 313, 17.
18. For a review of “second generation” antidepressant drugs, see Leonard, B. E. Neuropharmacology 1980, 19, 1175.
19. Marini-Bettolo, G. B.; Renzi, L.; Milani, C.; Bovet, D. Rend. 1st. Super. Sanita 1959, 22, 207;
20. Chem. Abstr. 1960, 54, 1522h.
21. Leonard, F.; Koo, J. Belgian Patent 613 211, 1962;
22. Chem. Abstr. 1962, 57, 16633c.
23. Leonard, F.; Koo, J. U.S. Patent 3 149 108; 1964;
24. Chem. Abstr. 1964, 61, 13320a.
25. Adachi, J.; Sato, N. J. Org. Chem. 1972, 37, 221.
26. Chapleo, C. B.; Myers, P. L. Tetrahedron Lett. 1981, 4839.
27. Krapcho, J.; Lott, W. A. U.S. Patent 2979 511, 1961
28. Chem. Abstr. 1961, 55, 18780d
29. Mouille, P.; Dabire, H.; Fournier, B.; Schmitt, H. Eur. J. Pharmacol. 1981, 73, 367.
30. Mouille, P.; Dabire, H.; Andrejak, M.; Schmitt, H. C. R. Hebd. Seances Acad. Sci. 1980, 290, 1553.
31. Augstein, J.; Green, S. M.; Monro, A. M.; Potter, G. W. H.; Worthing, C. R.; Wrigley, T. I. J. Med. Chem. 1965, 8, 446.
32. Brown, C. M.; McGrath, J. C.; Summers, R. J. Br. J. Pharmacol. 1979, 66, 553.
33. Kasuya, Y.; Suzuki, N. Arch. Int. Pharmacodyn. 1979, 241, 24.
34. McGrath, J. C. J. Physiol. 1978, 283, 23.
35. Docherty, J. R.; MacDonald, A.; McGrath, J. C. Br. J. Pharmacol. 1979, 67, 421P.
36. Flavahan, N. A.; McGrath, J. C. Br. J. Pharmacol. 1981, 72, 585P.
37. 2-adrenoceptor antagonist: Chapleo, C. B.; Doxey, J. C.; Myers, P. L.; Roach, A. G. Br. J. Pharmacol. 1981, 74, 842.
38. Timmermans, P. B. M. W. M.; Van Zwieten, P. A. Prog. Brain Res. 1977, 47, 391.
39. Timmermans, P. B. M. W. M.; Brands, A.; Van Zwieten, P. A. Arch. Pharm. (Weinheim, Ger.) 1977, 300, 217.
40. Arunlakshana, O.; Schild, H. O. Br. J. Pharmacol. 1959, 14, 48.