Indene-based frameworks targeting the 5-HT6 serotonin receptor: Ring constraint in indenylsulfonamides using cyclic amines and structurally abbreviated counterparts

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 20, 2009, Pages 7387-7397

  Alcalde, Ermitas ^a   Mesquida, Neus ^a   López Pérez, Sara ^a   Frigola, Jordi ^b   Mercè, Ramon ^b   Holenz, Jörg ^b   Pujol, Marta ^b   Hernández, Enrique ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b ESTEVE   (Spain)

Author keywords

5 HT6; Antagonists; Conformational restriction; Indenes; Serotonin receptors; Sulfonamides

Indexed keywords

6 CHLORO N [3 (1 METHYLPYRROLIDIN 3 YL) 1H INDEN 5 YL]IMIDAZO[2,1 B][1,3]THIAZOLE 5 SULFONAMIDE; CYCLIC AMP; INDENE DERIVATIVE; PYRROLIDINE DERIVATIVE; SEROTONIN 6 ANTAGONIST; SEROTONIN 6 RECEPTOR; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HUMAN; HUMAN CELL;

AMINES; CELL LINE; CYCLIC AMP; CYCLIZATION; HUMANS; INDENES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; RECEPTORS, SEROTONIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFONAMIDES;

EID: 71749110954     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.08.006     Document Type: Article

References (28)

1. Alcalde E., Mesquida N., López-Pérez S., Frigola J., and Mercè R. J. Med. Chem. 52 (2009) 675
2. Glennon R.A. J. Med. Chem. 46 (2003) 2795
3. Liu K.G., and Robichaud A.J. Drug Dev. Res. 70 (2009) 145
4. Johnson C.N., Ahmed M., and Miller N.D. Curr. Opin. Drug Discovery Dev. 11 (2008) 642
5. Geldenhuys W.J., and Van der Schyf C.J. Curr. Top. Med. Chem. 8 (2008) 1035
6. Heal D.J., Smith S.L., Fisas A., Codony X., and Buschmann H. Pharmacol. Ther. 117 (2008) 207
7. Nichols D.E. Chem. Rev. 108 (2008) 1614
8. Glennon R.A., Lee M., Rangisetty J.B., Dukat M., Roth B.L., Savage J.E., McBride A., Rauser L., Hufesien S., and Lee D.K.H. J. Med. Chem. 43 (2000) 1011
9. Tsai Y., Dukat M., Slassi A., MacLean N., Demchyshyn L., Savage J.E., Roth B.L., Hufesein S., Lee M., and Glennon R.A. Bioorg. Med. Chem. Lett. 10 (2000) 2295
10. Mercè, R.; Andaluz, B.; Frigola, J. World Patent WO 2003042175 A1, 2003; Chem. Abstr. 2003, 138, 401602.
11. Holenz J., Mercè R., Díaz J.L., Guitart X., Codony X., Dordal A., Romero G., Torrens A., Mas J., Andaluz B., Hernández S., Monroy X., Sánchez E., Hernández E., Pérez R., Cubí R., Sanfeliu O., and Buschmann H. J. Med. Chem. 48 (2005) 1781
12. Fisas A., Codony X., Romero G., Dordal A., Giraldo J., Mercè R., Holenz J., Heal D., Buschmann H., and Pauwels P.J. Br. J. Pharmacol. 148 (2006) 973
13. Cole D.C., Stock J.R., Lennox W.J., Bernotas R.C., Ellingboe J.W., Boikess S., Coupet J., Smith D.L., Leung L., Zhang G.-M., Feng X., Kelly M.F., Galante R., Huang P., Dawson L.A., Marquis K., Rosenzweig-Lipson S., Beyer C.E., and Schechter L.E. J. Med. Chem. 50 (2007) 5535
14. Schechter L.E., Lin Q., Smith D.L., Zhang G., Shan Q., Platt B., Brandt M.R., Dawson L.A., Cole D., Bernotas R., Robichaud A., Rosenzweig-Lipson S., and Beyer C.E. Neuropsychopharmacology (2007) 1
15. Abate C., Kolanos R., Dukat M., Setola V., Roth B.L., and Glennon R.A. Bioorg. Med. Chem. Lett. 15 (2005) 3510
16. Cole D.C., Lennox W.J., Stock J.R., Ellingboe J.W., Mazandarani H., Smith D.L., Zhang G., Tawa G.J., and Schechter L.E. Bioorg. Med. Chem. Lett. 15 (2005) 4780 and references cited therein
17. Cole D.C., Lennox W.J., Lombardi S., Elligboe J.W., Bernotas R.C., Tawa G.J., Mazandarani H., Smith D.L., Zhang G., Coupet J., and Schechter L.E. J. Med. Chem. 48 (2005) 353
18. Schechter L.E., Ring R.H., Beyer C.E., Hughes Z.A., Khawaja X., Malberg J.E., and Rosenzwieg-Lipson S. J. Am. Soc. Exp. NeuroTher. 2 (2005) 590
19. Pullagurla M.R., Dukat M., Setola V., Roth B., and Glennon R.A. Bioorg. Med. Chem. Lett. 13 (2003) 3355
20. Siripurapu U., Kolanos R., Dukat M., Roth B.L., and Glennon R.A. Bioorg. Med. Chem Lett. 16 (2006) 3793
21. Sikazwe D., Bondarev M.L., Dukat M., Rangisetty J.B., Roth B.L., and Glennon R.A. J. Med. Chem. 49 (2006) 5217
22. Dukat M., Philip D., Mosier P.D., Kolanos R., Roth B.L., and Glennon R.A. J. Med. Chem. 51 (2008) 603 and references cited therein
23. Alcalde E., Mesquida N., Frigola J., López-Pérez S., and Mercè R. Org. Biomol. Chem. 6 (2008) 3795 and references cited therein
24. Frigola, J.; Mercè, R.; Holenz, J.; Alcalde, E.; Mesquida, N.; López-Pérez, S. World Patent WO 2007054257 A2, 2007; Chem. Abstr. 2007, 146, 521555.
25. Roth B.L., Craigo S.C., Choudhary M.S., Uluer A., Monsma Jr. F.J., Shen Y., Meltzer H.Y., and Sibley D.R. J. Pharmacol. Exp. Ther. 268 (1994) 1403
26. Munson P.J., and Rodbard D. Anal. Biochem. 107 (1980) 220
27. Romero G., Sánchez E., Pujol M., Pérez P., Codony X., Holenz J., Buschmann H., and Pauwels P.J. Br. J. Pharmacol. 148 (2006) 1133
28. Romero G., Pujol M., Pérez P., Buschmann H., and Pauwels P.J. J. Pharmacol. Toxicol. Methods 55 (2007) 144