5-HT1D receptor agonist properties of novel 2-[5-[[(trifluoromethyl)sulfonyl]oxy]indolyl]ethylamines and their use as synthetic intermediates

Journal of Medicinal Chemistry

Volumn 39, Issue 24, 1996, Pages 4717-4726

  Barf, Tjeerd A ^a   De Boer, Peter ^a   Wikström, Håkan ^a   Peroutka, Stephen J ^b   Svensson, Kjell ^c   Ennis, Michael D ^c   Ghazal, Nabil B ^c   McGuire, James C ^c   Smith, Martin W ^c  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b Spectra Biomedical Inc   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYINDOLEACETIC ACID; 5 HYDROXYTRYPTOPHAN; ACRYLAMIDE DERIVATIVE; CYCLIC AMP; ETHYLAMINE; RECOMBINANT PROTEIN; SEROTONIN; SEROTONIN ANTAGONIST; SEROTONIN RECEPTOR; 3 [3 (2 DIMETHYLAMINOETHYL) 1H INDOL 5 YL] N (4 METHOXYBENZYL)ACRYLAMIDE; FORSKOLIN; SEROTONIN 1D AGONIST; SEROTONIN 1D RECEPTOR; SUMATRIPTAN; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; BRAIN; CHEMICAL STRUCTURE; CHO CELL; DRUG EFFECT; GENETICS; GUINEA PIG; HAMSTER; HUMAN; HYPOTHERMIA; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; STRUCTURE ACTIVITY RELATION; SYNTHESIS; ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; CONTROLLED STUDY; DEPRESSION; DRUG BRAIN LEVEL; DRUG PENETRATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MALE; MIGRAINE; NONHUMAN; RECEPTOR AFFINITY; SEROTONIN RELEASE; SUBCUTANEOUS DRUG ADMINISTRATION;

5-HYDROXYTRYPTOPHAN; ACRYLAMIDES; ANIMALS; BRAIN; CHO CELLS; CRICETINAE; CYCLIC AMP; ETHYLAMINES; GUINEA PIGS; HUMANS; HYDROXYINDOLEACETIC ACID; HYPOTHERMIA; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MOLECULAR STRUCTURE; RATS; RECEPTORS, SEROTONIN; RECOMBINANT PROTEINS; SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030300023     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9604890     Document Type: Article

References (50)

1. 3H]-5-hydroxytryptamine binding subtype in bovine brain membranes. J. Neurosci. 1987, 7, 894-903.
2. 1D recognition sites: Radioligand binding studies in human, pig and calf brain membranes. Naunyn-Schmiedeberg's Arch. Pharmacol. 1988, 337, 595-601.
3. Hoyer, D.; Middlemiss, D. N. Species differences in the pharmacology of terminal 5-HT autoreceptors in mammalian brain. Trends. Pharmacol. Sci. 1989, 10, 130-132.
4. 1D serotonin autoreceptors in human cerebral cortex. J. Neurochem. 1993, 60, 1179-1182.
5. 1D receptor genes. Trends Pharmacol. Sci. 1992, 13, 152-159.
6. 1Dβ. Proc. NaU. Acad. Sci. U.S.A. 1992, 89, 3630-3634.
7. Hoyer, D.; Clarke, D. E.; Fozard, J. R.; Hartig, P.; Martin, G. R.; Mylecharane, E. J.; Saxena, P. R.; Humprey, P. P. A. VII. International Union of Pharmacology Classification of Receptors for 5-Hydroxytryptamine (Serotonin). Pharmacol. Rev. 1994, 46, 157-203.
8. 1Dβ receptor subtype in human and bovine cerbral arteries. Mol. Pharmacol. 1993, 44, 242-246.
9. 1 receptors mediating contraction in bovine cerebral arteries: a model for human cerebrovascular '5-HT1Dβ' receptors. Eur. J. Pharmacol. 1993, 242, 75-82.
10. (a) Ferrari, M. D.; Saxena, P. R. Clinical and experimental effects of sumatriptan in humans. Trends Pharmacol. Sci. 1993, 14, 129-133.
11. (b) Peroutka, S. J.; McCarthy, B. G. Sumatriptan (GR 43175) interacts selectively with 5-HTiB and 5-HTiD binding sites. Eur. J. Pharmacol. 1989, 63, 133-136.
12. 1D Receptors. J. Med. Chem. 1995, 38, 1799-1810.
13. 1D Receptor: Discovery of Compounds with Potential Anti-Migraine Properties. J. Med. Chem. 1995, 38, 3566-3580.
14. 1 receptors in migraine pathophysiology and treatment. Eur. J. Neurol. 1995, 2, 5-21.
15. 1D Antagonists. J. Med. Chem. 1994, 37, 2253-2257.
16. 1Dβ receptors. Eur. J. Pharmacol. 1995, 287, 79-84.
17. 1D receptor antagonists. Exp. Opin. Invest. Drugs. 1995, 4, 323-331.
18. 1D Serotonin Receptors: Results of a Structure-Affinity Investigation. Drug Dev. Res. 1991, 22, 25-36.
19. 1D Receptor. J. Med. Chem. 1994. 37, 3023-3032.
20. 1D Receptors. J. Med. Chem. 1998, 38, 3602-3607.
21. (a) Macor, J. E.; Blank, D. H.; Post, R. J.; Ryan, K. The Synthesis of Conformationally Restricted Analog of the Anti-migraine Drug Sumatriptan. Tetrahedron Lett. 1992, 33, 8011-8014.
22. 1D Receptor. J. Med. Chem. 1993, 36, 1918-1919.
23. 1D Receptor Selectivity. J. Med. Chem. 1994, 37, 2509-2512.
24. (a) Sonesson, C.; Boije, M.; Svensson, K.; Ekman, A.; Carlsson, A.; Romero, A. G.; Martin, I. J.; Duncan, J. N.; King, L. J.; Wikström, H. Orally Active Central Dopamine and Serotonin Receptor Ligands: 5-, 6-, 7- and 8-[(Trifluoromethyl)sulfonyl]-oxy-2-(di-n-propylamino)tetralins and the Formation of Active Metabolites in Vivo. J. Med. Chem. 1993, 36, 3409-3416.
25. (b) Sonesson, C.; Barf, T.; Nilsson, J.; Dijkstra, D.; Carlsson, A.; Svensson, K.; Smith, M. W.; Martin, I. J.; Duncan, J. N.; King, L. J.; Wikström, H. Synthesis and Evaluation of Pharmacological and Pharmacokinetic Properties of Monopropyl Analogs of 5-, 7- and 8-[[(Trifluoromethyl)sulfonyl]oxy]-2-aminotetralins, J. Med. Chem. 1995, 38, 1319-1329.
26. 1A Receptors. J. Med. Chem. 1993, 36, 4221-4229.
27. 2-Receptor Antagonists. J. Med. Chem. 1995, 38, 150-160.
28. Sonesson, C.; Lin, C.-H.; Hansson, L.; Waters, N.; Svensson, K.; Carlsson, A.; Smith, M. W.; Wikström, H. Substituted (S)-Phenylpiperidines and Rigid Congeners as Preferential Dopamine Autoreceptor Antagonists: Synthesis and Structure-Activity Relationships. J. Med. Chem. 1994, 37, 2735-2753.
29. (a) Speeter, M. E.; Anthony, W. C. The action of oxalyl chloride on indoles: a new approach to tryptamines. J. Am. Chem. Soc. 1954, 76, 6208-6210.
30. (b) Kondo, H.; Kataoka, H.; Hayashi, Y.; Dodo, T. Chem. Abstr. 1960, 54, 492.
31. Hendrickson, J. B.; Bergeron, R. Triflamides: New acylating and Inflating reagents. Tetrahedron Lett. 1973, 4607-4610.
32. De Silva, S. O.; Snieckus, V. Indole N-alkylation of tryptamines via dianion and phthalimido intermediates. New potential indolealkylamine haptens. Can. J. Chem. 1978, 56, 1621-1627.
33. Kukolja, S.; Lammert, S. R. Azetidone antibiotics. XIV. Removal of a phthaloyl protective group from acid and base sensitive compounds. J. Am. Chem. Soc. 1975, 97, 5582-5583.
34. Veldman, S. A.; Bienkowski, M. J. Cloning and Pharmacological Characterization of a Novel Human 5-Hydroxytryptamine-1D Receptor Subtype. Mol. Pharmacol. 1992, 42, 439-444.
35. 1A Agonist. J. Pharmacol. Exp. Ther. 1994, 271, 875-883.
36. 1A autoreceptors in the raphe nuclei. Trends Pharmacol. Sci. 1986, 7, 212-214.
37. Shum, A.; Sole, M. J.; van Loon, G. R. Simultaneous measure-ment of 5- hydroxytryptophan and L-dihydroxyphenylalanine by high performance liquid chromatography with electrochemical detection. Measurement of serotonin and catecholamine turnover in discrete brain areas. J. Chromatogr. 1982, 228, 123-130.
38. 1Dβ Serotonin Receptor Agonist. J. Med. Chem. 1994, 37, 2828-2830.
39. 1D receptors causes hypothermia in the guinea-pig. J. Psychopharmacol. 1994, 8, 14-21.
40. Saxena, P. R.; De Vries, P.; Heiligers, J. P. C.; Maassen-Van Den Brink, A.; Barf, T.; Wikström, H. Investigation with GMC2021, a triflated analogue of sumatriptan, in experimental models predictive of antimigraine activity and coronary side-effect potential. Eur. J. Pharmacol. 1996, 312, 53-62.
41. Pallas version 1.2 is commercially available software of CompuDrug Chemistry Ltd., 1994.
42. 2 dopamine receptor in rat and bovine caudate nucleus. Nature 1990, 343, 266-269.
43. 1A receptor. Nature 1988, 335, 358-360.
44. Cheng, Y. C.; Prushoff, W. H.; Relationship Between the Inhibition Constant and the Concentration of Inhibitor which Causes 50 Percent Inhibition of Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
45. 1B receptors. Nature 1992, 360, 161-163.
46. 1B receptor. J. Biol. Chem. 1992, 267, 5735-5738.
47. McPherson, G. A. A Computer-based Approach to the Analysis of Radioligand Binding Experiments. Comput. Prog. Biomed. 1983, 17, 107-114.
48. Munson, P. J.; Rodbard, D. Ligand: A versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 1980, 107, 220-239.
49. Santiago, M.; Westerink, B. H. C. Role of adenylate cyclase in the release of dopamine: A microdialysis study in the striatum of the rat. J. Neurochem. 1990, 55, 169-174.
50. Paxinos, G.; Watson, C. Rat Brain in Stereotaxic Coordinates; Academic Press: New York, 1982.