2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors

Journal of Medicinal Chemistry

Volumn 43, Issue 5, 2000, Pages 1011-1018

  Glennon, Richard A ^a   Lee, Mase ^a   Rangisetty, Jagadeesh B ^a   Dukat, Malgorzata ^a   Roth, Bryan L ^b   Savage, Jason E ^b   McBride, Ace ^b   Rauser, Laura ^b   Hufeisen, Sandy ^b   Lee, David K H ^c  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

^b CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c NPS Pharmaceutical Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SEROTONIN 6 RECEPTOR; SEROTONIN AGONIST; TRYPTAMINE DERIVATIVE;

ARTICLE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; KIDNEY CELL;

ADENYLATE CYCLASE; CELL LINE; ENZYME ACTIVATION; HUMANS; METHOXYDIMETHYLTRYPTAMINES; RADIOLIGAND ASSAY; RECEPTORS, SEROTONIN; SEROTONIN AGONISTS; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPTAMINES;

EID: 0034624773     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990550b     Document Type: Article

References (28)

1. 6) receptor: molecular cloning, localization, and stimulation of cAMP accumulation. Biochim. Biophys. Acta 1993, 193, 268-276.
2. 6 receptor: localization and function. Exp. Opin. Ther. Patents 1998, 8, 1217-1224.
3. 6 serotonin receptor. J. Neurochem. 1996, 66, 47-56.
4. Roth, B. L.; Craigo, S. C.; Choudhary, M. S.; Uluer, A.; Monsma, F. J.; Shen, Y.; Meltzer, H. Y.; Sibley, D. R. Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J. Pharmacol. Exp. Ther. 1994, 268, 1403-1410.
5. 6 serotonin receptors may reflect psychoactive profile. Mol. Med. 1995, 1, 398-406.
6. 6 receptors in the rat brain: A study using antisense oligonucleotides. J. Pharmacol. Exp. Ther. 1995, 274, 173-180.
7. 6 expression in the rat: functional studies using antisense oligonucleotides. Behav. Brain Res. 1996, 73, 245-248.
8. 6 receptors. Neuropsychopharmacology 1999, 21, 68S-76S.
9. 6 receptor subtype in the rat brain. Life Sci. 1998, 62, 1473-1477.
10. 6 receptor-like material in the rat central nervous system. Brain Res. 1997, 746, 207-219.
11. 6 receptor mRNA in the rat brain during ontogenetic development. Naunyn-Schmeideberg's Arch. Pharmacol. 1998, 357, 393-400.
12. 6 receptors. Br. J. Pharmacol. 1998, 124, 556-562.
13. 3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum. Mol. Pharmacol. 1998, 54, 577-583.
14. 6 receptor antagonist. J. Med. Chem. 1999, 42, 202-205.
15. Monsma, F. J.; Shey, Y.; Ward, R. P.; Hamblin, M. W.; Sibley, D. R. Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs. Mol. Pharmacol. 1993, 43, 20-327.
16. Glennon, R. A.; Dukat, M.; Westkaemper, R. B. Serotonin receptors and ligands. In Psychopharmacology; Watson, S. J., Ed.; Lippencott-Raven: New York, 1998; CD-ROM version.
17. 6 serotonin receptor binding of indolealkylamines: A preliminary structure-affinity investigation. Med. Chem. Res. 1999, 9, 108-117.
18. Shaw, E. The synthesis of tryptamines related to serotonin. J. Am. Chem. Soc. 1955, 77, 4319-4324.
19. Polyphosphate ester (PPE) in Reagents for Organic Synthesis, Volume 1; Fieser, L. F., Fieser, M., Eds.; John Wiley and Sons: New York, 1967; pp 892-894.
20. Alexander, E.; Mooradian, A. 4-Aminomethyl-9-benzyl-1,2,3,4-tetrahydrocarbazoles. United States Patent 3,939,177, Feb 17, 1976.
21. 3 receptors. In Serotonin Receptors and their Ligands; Olivier, B., van Wijngaarden, I., Soudijn, W., Eds.; Elsevier: Amsterdam, 1997; pp 221-258.
22. 1D receptor. J. Med. Chem. 1993, 36, 1918-1919.
23. 1Dβ receptors. J. Med. Chem. 1996, 39, 314-322.
24. Julia, M.; Melamed, R.; Gombert, R. Research in the indole series. XVI. 2-Aryltryptamines and homologous amines. Ann. Inst. Pasteur 1965, 109, 343-362; Chem. Abstr. 1966, 64, 677.
25. Julia, M.; Melamed, R.; Gombert, R. Research in the indole series. XVI. 2-Aryltryptamines and homologous amines. Ann. Inst. Pasteur 1965, 109, 343-362; Chem. Abstr. 1966, 64, 677.
26. Benington, F.; Morin, R. D.; Clark, L. C. Jr. Synthesis of O- and N-methylated derivatives of 5-hydroxytryptamine. J. Org. Chem. 1958, 23, 1977-1979.
27. Chapman, N. B.; Clarke, K.; Hughes, H. Synthesis of some 5-substituted 2-methyltryptamines and their N-mono- and dialkyl derivatives. J. Chem. Soc. 1965, 1424-1428.
28. Houlihan, W. J.; Parrino, V. A.; Uike, Y. Lithiation of N-(2-alkylphenyl)alkanamides and related compounds. Madelung indole synthesis. J. Org. Chem. 1981, 46, 4511-4515.