Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 314-322

  Glennon, Richard A ^a   Hong, Seoung Soo ^a   Bondarev, Mikhail ^a   Law, Ho ^a   Dukat, Malgorzata ^a   Rakhit, Suman ^b   Power, Patricia ^b   Fan, Ermei ^b   Kinneau, Diana ^b   Kamboj, Rajender ^b   Teitler, Milt ^c   Herrick Davis, Katharine ^c   Smith, Carol ^c  

^a VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Allelix Biopharmaceutical Inc   (Canada)

^c ALBANY MEDICAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (NONYLOXY)TRYPTAMINE; 5 [(7,7 DIMETHYLHEPTYL)OXY]TRYPTAMINE; ALKYL GROUP; CARBONYL DERIVATIVE; OXYGEN; SEROTONIN 1A RECEPTOR; SEROTONIN 1D RECEPTOR; SEROTONIN DERIVATIVE; SUMATRIPTAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING SITE; CHO CELL; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; MIGRAINE; MONKEY; NONHUMAN; RECEPTOR AFFINITY;

EID: 13344282760     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950498t     Document Type: Article

References (29)

1. Glennon, R. A.; Dukat, M. Serotonin receptor subtypes. In Psychopharmacology: The Fourth Generation of Progress; Bloom, F., Kupfer, M., Eds.; Raven Press: New York, 1994; pp 415-429.
2. (a) Martin, G. R.; Humphrey, P. P. A. Receptors for 5-hydroxytryptamine: Current perspectives on classification and nomenclature. Neuropharmacology 1994, 33, 261-273.
3. (b) 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. 1994, 46, 157-203.
4. Saudou, F.; Hen, R. 5-HT receptor subtypes: Molecular and functional diversity. Med. Chem. Res. 1994, 4, 16-84.
5. Doucet, E.; Pohl, M.; Fattaccini, C.-M.; Adrien, J.; El Mestikawy, S.; Hamon, M. In situ hybridization evidence for the synthesis of 5-HT1B receptor in serotonergic neurons of anterior raphe nuclei in the rat brain. Synapse 1995, 19, 18-28.
6. Glennon, R. A.; Westkaemper, R. B. 5-HT1D receptors: A serotonin receptor population for the 1990s. Drug News Perspect. 1993, 6, 390-405.
7. Zifa, E.; Fillion, G. 5-hydroxytryptamine receptors. Pharmacol. Rev. 1992, 44, 401-458.
8. Ferrari, M. D.; Saxena, P. R. Clinical and experimental effects of sumatriptan in humans. Trends Pharmacol. Sci. 1993, 14, 129-133.
9. Weinshank, R. L.; Zgombic, J. M.; Macchi, M. J.; Branchek, T. A.; Hartig, P. R. Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1Dα and 5-HT1Dβ. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3630-3634.
10. Street, L. J.; Baker, R.; Castro, J. L ; Chambers, M. S.; Guiblin, A. R.; Hobbs, S. C.; Matassa, V. G.; Reeve, A. J.; Beer, M. S.; Middlemiss, D. N.; Noble, A. J.; Stanton, J. A.; Scholey, K.; Hargreaves, R. J. Synthesis and serotonergic activity of 5-(oxadiazolyl)tryptamines: Potent agonists for 5-HT1D receptors. J. Med. Chem. 1993, 36, 1529-1538.
11. King, F. D.; Brown, A. M.; Gaster, L. M.; Kaumann, A. J.; Medhurst, A. D.; Parker, S. G.; Parsons, A. A.; Patch, T. L.; Raval, P. (±)3-Amino-6-carboxamido-1,2,3,4-tetrahydrocarbazole: A conformationally restricted analogue of 5-carboxamidotryptamine with selectivity for the serotonin 5-HT1D receptor. J. Med. Chem. 1993, 36, 1918-1919.
12. Macor, J. E.; Blank, D. H.; Fox, C. B.; Lebel, L. A.; Newman, M. E.; Post, R. J.; Ryan, K.; Schmidt, A. W.; Schulz, D. W.; Koe, B. K. 5-[(3-Nitropyrid-2-yl)amino]indoles: Novel serotonin agonists with selectivity for the 5-HT1D receptor. Variation of the C3 substituent on the indole template leads to increased 5-HT1D receptor selectivity. J. Med. Chem. 1994, 37, 2509-2512.
13. Clitherow, J. W.; Scopes, D. I. C.; Skingle, M.; Jordan, C. C.; Feniuk, W.; Campbell, I. B.; Carter, M. C.; Collington, E. W.; Connor, H. E.; Higgins, G. A.; Beattie, D.; Kelly, H. A.; Mitchell, W. L.; Oxford, A. W.; Wadsworth, A. H.; Tyers, M. B. Evolution of a novel series of [N,N-dimethylamino)propyl]- and piperazinylbenzanilides as the first selective 5-HT1D antagonists. J. Med. Chem. 1994, 37, 2253-2257.
14. Glennon, R. A. Concepts for the design of 5-HT1A agonists and antagonists. Drug Dev. Res. 1992, 26, 251-274.
15. Glennon, R. A.; Ismaiel, A. M.; Chaurasia, C.; Titeler, M. 5-HT1D receptors: Results of a structure-affinity investigation. Drug. Dev. Res. 1991, 22, 25-36.
16. Glennon, R. A.; Hong, S.-S.; Dukat, M.; Teitler, M.; Davis, K. 5-(Nonyloxy)tryptamine: A novel high-affinity 5-HT1Dβ serotonin receptor agonist. J. Med. Chem. 1994, 37, 2828-2830.
17. Friedman, L.; Shani, A. Halopolycarbon homologation. J. Am. Chem. Soc. 1974, 36, 7101-7103.
18. Cason, J. Branched chain fatty acids. I. Synthesis of 17-methyloctadecanoic acid. J. Am. Chem. Soc. 1942, 64, 1106-1110.
19. Gutman, E. M.; Hickinbottom, W. J. The synthesis and reactions of branched-chain hydrocarbons. Part II. Hydrocarbons with two or more quaternary carbon atoms. J. Chem. Soc. 1951, 3344-3347.
20. Hiers, G. S.; Adams, R. Omega-cyclohexyl derivatives of various normal aliphatic acids. J. Am. Chem. Soc. 1926, 26, 2385-2395.
21. Speeter, M. E.; Anthony, W. C. The action of oxalyl chloride on indoles. A new approach to tryptamine. J. Am. Chem. Soc. 1954, 76, 6208-6210.
22. Sugasawa, T.; Adachi, M.; Sasakuwa, K.; Kitagawa, A. Amino-haloborane in organic synthesis. Simple synthesis of indoles and 1-acyl-3-indoline using specific ortho α-chloroacetylation of anilines. J. Org. Chem. 1979, 44, 578-586.
23. von Strandtmann, M.; Cohen, M. P.; Shavel, J.; Acyltryptamines II. Synthesis of acyltryptamines, indazoles, and azepinoindoles from the acylphenylhydrazones of 2,3-piperidinedione. J. Med. Chem. 1963, 6, 719-725.
24. Glennon, R. A.; Gessner, P. K.; Godse, D.; Kline, B. Bufotenine esters. J. Med. Chem. 1979, 22, 1414-1416.
25. Ismaiel, A. M.; Titeler, M.; Miller, K. J.; Smith, T. S.; Glennon, R. A. 5-HT1 and 5-HT2 binding profiles of the serotonergic agents α-methylserotonin and 2-methylserotonin. J. Med. Chem. 1990, 33, 755-758.
26. King, F. D.; Gaster, L. M.; Kaumann, A. J.; Young, R. C. Use of tetrahydrocarbazone derivatives as 5-HT1 receptor agonists. WO 93,00086, January 7, 1993.
27. Mooradian, A.; Dupont, P. E.; Hlavac, A. G.; Aceto, M. D.; Pearl, J. 3-Aminotetrahydrocarbazoles as a new series of central nervous system agents. J. Med. Chem. 1977, 20, 487-492
28. Demchyshyn, L.; Sunahara, R. K.; Miller, K.; Teitler, M.; Hoffman, J. B.; Kennedy, J. L.; Seeman, P.; Van Tol, H. M.; Niznik, H. B. A human serotonin 1D receptor variant (5-HT1Dβ) encoded by an intronless gene on chromosome 6. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5522-5526.
29. Herrick-Davis, K.; Teitler, M.; Leonhardt, S.; Struble, R.; Price, D. Serotonin 5-HT1D receptors in human prefrontal cortex and caudate: Interaction with a GTP binding protein. J. Neurochem. 1988, 51, 1906-1912.