Synthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: Novel antagonists for the vascular 5-HT1B receptor

European Journal of Medicinal Chemistry

Volumn 39, Issue 4, 2004, Pages 305-321

  Moloney, Gerard P ^a   Garavelas, Agatha ^a   Martin, Graeme R ^b   Maxwell, Miles ^c   Glen, Robert C ^d  

^a MONASH UNIVERSITY   (Australia)

^b ROCHE BIOSCIENCE   (United States)

^c GLAXOSMITHKLINE   (United Kingdom)

^d TRIPOS INC   (United States)

Author keywords

5 HT1B receptor; Antagonist; DIAD; Diisopropyl azidicarboxylate; Diisopropylethylamine; DIPEA; Molecular modeling; NaCNBH 3; O Benzothiazol 1 yl N,N,N ,N , tetramethyluronium tetrafluoroborate; Synthesis; TBTU

Indexed keywords

(3 AMIDO)PHENYLPIPERAZINE; AMIDE; ANGIOTENSIN; BENZOTHIOPHENE DERIVATIVE; N (2 ETHYLPHENYL) 4 (4 METHYL 1 PIPERAZINYL) 1 BENZO[B]THIOPHENE 2 CARBOXAMIDE; N [4 (4 CHLOROPHENYL) 4 (4 METHYL 1 PIPERAZINYL)]BENZAMIDE; PHENYL GROUP; PIPERAZINE DERIVATIVE; SEROTONIN ANTAGONIST; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BLOOD VESSEL; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG IDENTIFICATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FEMORAL ARTERY; NONHUMAN; RABBIT; SEROTONINERGIC SYSTEM; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

AMIDES; ANIMALS; AORTA; BINDING, COMPETITIVE; CORONARY VESSELS; DOSE-RESPONSE RELATIONSHIP, DRUG; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PIPERAZINES; RABBITS; RECEPTOR, SEROTONIN, 5-HT1B; SAPHENOUS VEIN; SEROTONIN ANTAGONISTS; THIOPHENES;

EID: 1842557494     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2003.12.008     Document Type: Article

References (30)

1. Hoyer D., Clarke D.E., Fozard J.R., Hartig P.R., Martin G.R., Mylecharane E.J., Saxena P.R., Humphrey P.P.A. International union of pharmacology classification of receptors for 5-hydroxytryptamine (serotonin). Pharmacol. Rev. 46:1994;157-204.
2. Martin G.R., Humphrey P.P.A. Receptors for 5-hydroxy tryptamine: current perspectives on classification and nomenclature. Neuropharmacology. 33:1994;261-273.
3. Hoyer D., Martin G.R. 5-HT receptor classification and nomenclature: towards a harmonisation with the human genome. Neuropharmacology. 36:1997;419-428.
4. Vanhoutte P.M., Humphrey P.P.A., Spedding M. Recommendations for nomenclature of new receptor subtypes. Pharmacol. Rev. 48:1996;1-2.
5. 1D receptor subtypes. Trends Pharmacol. Sci. 17:1996;103-105.
6. 1-like receptor in dog isolated saphenous vein. Br. J. Pharmacol. 94:1988;1123-1132.
7. Dechant K.L., Clissold S.P. Sumatriptan. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headache. Drugs. 43:1992;776-798.
8. North P.C. Migraine therapy - serotonin to sumatriptan. King F.G. Medicinal Chemistry: Principles and Practice. 1994;The Royal Society of Chemistry.
9. 1D agents for the acute treatment of migraine headache. Headache. 34:1994;307.
10. 1D receptors: pharmacology and therapeutic potential. Serotonin ID Research Alert. 1:1996;19-29.
11. G.R. Martin, Serotonin Receptor Involvement in the Pathogenesis and Treatment of Migraine, in: S. Silberstein, P.J. Goadsby (Eds.), Blue Books on Neurology, Butterworth-Heinemann, Boston,1997
12. European Patent EP 0 533 266 A1, (1992)
13. European Patent EP 0 533 267 A1, (1992)
14. European Patent EP 0 533 268 A1, J.W. D.I.C. (1992)
15. 1D antagonists. J. Med. Chem. 37:1994;2253-2257.
16. 1D receptor antagonist GR127935 on extracellular levels of 5-HT in the guinea-pig frontal cortex as measured by microdialysis. Neuropharmacology. 34:1995;377-382.
17. 1Dβ receptors. Eur. J. Pharmacol. 287:1995;79-84.
18. McFadden E.P., Clarke J.G., Davies G.J., Kaski J.C., Haider A.W., Maseri A. Effect of intracoronary serotonin on coronary vessels in patients with stable angina and patients with variant angina. New. Eng. J. Med. 324:1991;648-654.
19. Golino P., Piscione F., Willerson J.T., Cappelli-Bigazzi M., Focaccio A., Villari B., Indolfi C., Russolillo E., Condorelli M., Chiariello M. Divergent effects of serotonin on coronary artery dimensions and blood flow in patients with coronary atherosclerosis and control patients. New Eng. J. Med. 324:1991;641-648.
20. Maseri A. Pathogenetic components of acute ischemic syndromes. Focus on acute ischemic stimuli. Circulation. 81 (1 suppl.):1990;I1-I3.
21. Fitzgerald D.J., Roy L., Catella F., Fitzgerald G.A. Platelet activation in unstable coronary disease. New Eng. J. Med. 315:1986;983-989.
22. Bradley P.B., Engel G., Feniuk W., Fozard J.R., Humphrey P.P.A., Middlemiss D.N., Mylecharane E.J., Richardson B.P., Saxena P.R. Proposals for the classification and nomenclature of functional receptors for 5-hydroxytryptamine. Neuropharmacology. 25:1986;563-576.
23. Scherbel A.L., Harrison J.N. Response to serotonin and its antagonists in patients with rheumatoid arthritis and related diseases. Angiology. 10:1959;29-38.
24. 1B/1D receptor antagonists. J. Med. Chem. 40:1997;2347-2362.
25. Merrell Dow Pharmaceuticals, PCT/US93/08865.
26. 1B-like receptor. J. Med. Chem. 42:1999;2504-2526.
27. 1B-like receptors. J. Chem. Soc. Perkins Trans. 1:1999;2173-2723.
28. 1D receptor: discovery of compounds with potential anti-migraine properties. J. Med. Chem. 38:1995;3566-3580.
29. Martin G.R., MacLennan S.J. Analysis of the 5-HT receptor in rabbit saphenous vein exemplifies the problems of using exclusion criteria for receptor classification. Naunyn. Schmiedebergs. Arch. Pharmacol. 342:1990;111-119.
30. Sybyl 6.1 molecular modelling package. 1992;Tripos Associates, St. Louis, MO.