Binding of isotryptamines and indenes at h5-HT6 serotonin receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 8, 2005, Pages 1987-1991

  Kolanos, Renata ^a   Siripurapu, Uma ^a   Pullagurla, Manik ^a   Riaz, Mohamed ^a   Setola, Vince ^b   Roth, Bryan L ^b   Dukat, Małgorzata ^a   Glennon, Richard A ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

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

Author keywords

5 HT6; Binding requirements; Serotonergic ligands

Indexed keywords

INDENE DERIVATIVE; NITROGEN; SEROTONIN 6 RECEPTOR; TRYPTAMINE DERIVATIVE;

ALKYLATION; ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; OXIDATION KINETICS;

EID: 15944365224     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.02.070     Document Type: Article

References (29)

1. D. Hoyer, J.P. Hannon, and G.R. Martin Pharmacol. Biochem. Behav. 71 2002 533
2. W.K. Kroeze, K. Kristiansen, and B.L. Roth Curr. Top. Med. Chem. 2 2002 507
3. R. Kohen, M.A. Metcalf, N. Khan, T. Druck, K. Huebner, J.E. Lachowicz, H.Y. Meltzer, D.R. Sibley, B.L. Roth, and M.W. Hamblin J. Neurochem. 66 1996 47
4. B.L. Roth, S.C. Craigo, M.S. Choudhary, A. Uluer, F.J. Monsma Jr., Y. Shen, H.Y. Meltzer, and D.R. Sibley J. Pharmacol. Exp. Ther. 268 1994 1403
5. T.A. Brancheck, and T.P. Blackburn Annu. Rev. Pharmacol. 40 2000 319
6. M.L. Woolley, C.A. Marsden, and K.C.F. Fone Curr. Drug Top. 3 2004 59
7. R.A. Glennon J. Med. Chem. 46 2003 2795
8. A. Slassi, M. Isaac, and A. O'Brien Expert Opin. Ther. Pat. 12 2002 513
9. R.A. Glennon, M. Lee, J.B. Rangisetty, M. Dukat, B.L. Roth, J.E. Savage, A. McBride, L. Rauser, L. Hufesien, and D.K.H. Lee J. Med. Chem. 43 2000 1011
10. Y. Tsai, M. Dukat, A. Slassi, N. MacLean, L. Demchyshyn, J.E. Savage, B.L. Roth, S. Hufesein, M. Lee, and R.A. Glennon Bioorg. Med. Chem. Lett. 10 2000 2295
11. M. Lee, J.B. Rangisetty, M. Dukat, A. Slassi, N. MacLean, D.K.H. Lee, and R.A. Glennon Med. Chem. Res. 10 2000 230
12. M. Pullagurla, V. Setola, B.L. Roth, and R.A. Glennon Bioorg. Med. Chem. Lett. 13 2003 3355
13. J. Chang-Fong, J. Addo, M. Dukat, C. Smith, N.A. Mitchell, K. Herrick-Davis, M. Teitler, and R.A. Glennon Bioorg. Med. Chem. Lett. 12 2002 155
14. R.A. Glennon, J.M. Jacyno, R. Young, J.D. McKenney, and D. Nelson J. Med. Chem. 27 1984 41
15. S. Swaminathan, S. Ranganathan, and S. Sulochana J. Org. Chem. 5 1958 707
16. A.R. Katritzky, X. Lan, and J.N. Lam J. Org. Chem. 56 1991 4397
17. C. Quian, H. Li, J. Sun, and W. Nie J. Organomet. Chem. 585 1999 59
18. T.M. Bohme, C. Keim, G. Dannhardt, E. Mutschler, and G. Lambrecht Bioorg. Med. Chem. Lett. 11 2001 1241
19. P.H. Reggio, S. Basu-Dutt, J. Barnett-Norris, M.T. Castro, D.P. Hurst, H.H. Seltzman, M.J. Roche, A.F. Gilliam, B.F. Thomas, L.A. Stevenson, R.G. Pertwee, and M.E. Abood J. Med. Chem. 41 1998 5177
20. C.R. Ganellin, J.M. Loynes, H.F. Ridley, and R.G. Spickett J. Med. Chem. 10 1967 826
21. 4) were isolated as their oxalate salts following recrystallization from absolute EtOH. Both analyzed within 0.4% of theory for C, H, and N
22. 4S, and analyzed within 0.4% of theory for C, H, and N
23. J.B. Woell, and P. Boudjouk J. Org. Chem. 45 1980 5213
24. M. Fujio, J.R. Keeffe, R.A. More O'Ferrall, and A.C. O'Donoghue J. Am. Chem. Soc. 126 2004 9982
25. 3S) was obtained upon oxidation of 31 with oxone, and analyzed within 0.4% of theory for C, H, and N
26. W.D. Hirst, B. Abrahamsen, F.E. Blaney, A.R. Calver, L. Aloj, G.W. Price, and A.D. Medhurst Mol. Pharmacol. 64 2003 1295
27. M. Lee, J.B. Rangisetty, M.R. Pullagurla, M. Dukat, V. Setola, B.L. Roth, and R.A. Glennon Bioorg. Med. Chem. Lett. 15 2005 1707 1711
28. i values are the result of triplicate determinations
29. F.D. Bellamy, and K. Ou Tetrahedron Lett. 25 1984 839