Design, synthesis and pharmacological evaluation of 4-(piperazin-1-yl methyl)-N1-arylsulfonyl indole derivatives as 5-HT6 receptor ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 24, 2012, Pages 7431-7435

  Nirogi, Ramakrishna V S ^a   Badange, Rajeshkumar ^a,b   Kambhampati, Ramasastri ^a   Chindhe, Anil ^a   Deshpande, Amol D ^a   Tiriveedhi, Vinaykumar ^a   Kandikere, Vishwottam ^a   Muddana, Nageswararao ^a   Abraham, Renny ^a   Khagga, Mukkanti ^b  

^a SUVEN LIFE SCIENCES LTD   (India)

^b JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY   (India)

Author keywords

5 HT6R ligands; Cognitive impairment; Cross selectivity; ORT; PK profile; SAR

Indexed keywords

4 (PIPERAZIN 1 YL METHYL) N1 ARYLSULFONYL INDOLE DERIVATIVE; FUSED CARBON NITROGEN HETEROCYCLE; SEROTONIN 6 RECEPTOR; SEROTONIN RECEPTOR AFFECTING AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; COGNITIVE DEFECT; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALS; CYTOCHROME P-450 CYP2D6; CYTOCHROME P-450 CYP3A; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; ENZYME INHIBITORS; HEK293 CELLS; HUMANS; INDOLES; LIGANDS; MALE; MOLECULAR STRUCTURE; RATS; RATS, WISTAR; RECEPTORS, SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 84870239138     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.057     Document Type: Article

References (34)

1. B.L. Roth, S.M. Hanizavareh, and A.E. Blum Psychopharmacology 174 2004 17
2. G. Rosse, and H. Schaffhauser Curr. Top. Med. Chem. 10 2010 207
3. C. Wilson, and A.V. Terry Jr. Drugs Future 34 2009 969
4. C. Gerard, M.P. Martres, K. Lefevre, M.C. Miquel, D. Verge, L. Lanfumey, E. Doucet, M. Hamon, and S.E. Mestikawy Brain Res. 746 1997 207
5. F.J. Monsma, Y. Shen, R.P. Ward, M.W. Hamblin, and D.R. Sibley Mol. Pharmacol. 43 1993 320
6. M. Ruat, E. Traiffort, J.M. Arrang, J. Tardivellacombe, J. Diaz, R. Leurs, and J.C. Schwartz Biochem. Biophys. Res. Commun. 193 1993 268
7. 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
8. A.J. Sleight, F.G. Boess, M. Bos, B. Levet-Trafit, and A. Bourson Exp. Opin. Ther. Patents 8 1998 1217
9. L.A. Dawson, H.Q. Nguyen, and P. Li Neuropsychopharmacology 25 2001 662
10. L.A. Dawson, H.Q. Nguyen, and P. Li Br. J. Pharmacol. 130 2000 23
11. J. Arnt, and C.K. Olsen Int. Rev. Neurobiol. 96 2011 141
12. B.L. Roth, S.C. Craigo, M.S. Choudhary, A. Uluer, F.J. Monsma, Y. Shen, H.Y. Meltzer, and D.R. Sibley J. Pharmacol. Exp. Ther. 268 1994 1403
13. K.G. Liu, and A.J. Robichaud Drug Dev. Res. 70 2009 145
14. J. Holenz, P.J. Pauwels, J.L. Diaz, R. Merce, X. Codony, and H. Buschmann Drug Discovery Today 11 2006 283
15. X. Codony, J.M. Vela, and M.J. Ramirez Curr. Opin. Pharmacol. 11 2011 94
16. R. Emsley Expert Opin. Investig. Drugs 18 2009 1103
17. K.C.F. Fone Neuropharmacology 55 2008 1015
18. E.S. Mitchell, and J.F. Neumaier Pharmacol. Ther. 108 2005 320
19. R.A. Glennon, U. Siripurapu, B.L. Roth, R. Kolanos, M.L. Bondarev, D. Sikazwe, M. Lee, and M. Dukat Curr. Top. Med. Chem. 10 2010 579
20. S. Davies, J.S. Silvestre, and X. Guitart Drugs Future 30 2005 479
21. G. Maher-Edwards, R. Dixon, J. Hunter, M. Gold, G. Hopton, G. Jacobs, J. Hunter, and P. Williams Int. J. Geriatr. Psychiatry 26 2011 536
22. J. Arnt, B. Bang-Andersen, B. Grayson, F.P. Bymaster, M.P. Cohen, N.W. DeLapp, B. Giethlen, M. Kreilgaard, D.L. McKinzie, J.C. Neill, D.L. Nelson, S.M. Nielsen, M.N. Poulsen, J.M. Schaus, and L.M. Witten Int. J. Neuropsychopharmacol. 13 2010 1021
23. 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
24. M. Ahmed, M.A. Briggs, S.M. Bromidge, T. Buck, L. Campbell, N.J. Deeks, A. Garner, L. Gordon, D.W. Hamprecht, V. Holland, C.N. Johnson, A.D. Medhurst, D.J. Mitchell, S.F. Moss, J. Powles, J.T. Seal, T.O. Stean, G. Stemp, M. Thompson, B. Trail, N. Upton, K. Winbornc, and D.R. Witty Bioorg. Med. Chem. Lett. 15 2005 4867
25. K.G. Liu, and A.J. Robichaud Int. Rev. Neurobiol. 94 2010 1
26. R.A. Glennon J. Med. Chem. 46 2003 2795
27. R. Nirogi, A. Dwarampudi, R. Kambhampati, V. Bhatta, L. Kota, A. Shinde, R. Badange, P. Jayarajan, G. Bhyrapuneni, and P.K. Dubey Bioorg. Med. Chem. Lett. 21 2011 4577
28. R. Nirogi, A. Deshpande, R. Kambhampati, R. Badange, L. Kota, A. Daulatabad, A. Shinde, I. Ahmad, V. Kandikere, P. Jayarajan, and P.K. Dubey Bioorg. Med. Chem. Lett. 21 2011 346
29. R. Nirogi, A. Daulatabad, G. Parandhama, S. Mohammad, K.R. Sastri, A. Shinde, and P.K. Dubey Bioorg. Med. Chem. Lett. 20 2010 4440
30. R. Nirogi, P. Kothmirkar, R. Kambhampati, J. Konda, S. Arepalli, N. Pamuleti, A. Deshpande, T. Bandyala, A. Shinde, and P.K. Dubey ACS Med. Chem. Lett. 1 2010 340
31. R.D. Clark, and D.B. Repke Heterocycles 22 1984 195
32. A.D. Batcho, and W. Leimgruber Org. Synth. 63 1985 214
33. D.F.V. Lewis Cytochromes P450: Structure, Function and Mechanism 1996 Taylor and Francis Publishing London
34. A. Ennaceur, and J.P. Aggleton Behav. Brain Res. 88 1997 181