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Design, Synthesis and Biological Evaluation of Novel Benzopyran Sulfonamide Derivatives as 5-HT6 Receptor Ligands
Corresponding Author(s) : Ramakrishna V.S. Nirogi
Asian Journal of Chemistry,
Vol. 27 No. 6 (2015): Vol 27 Issue 6
Abstract
On the basis of a known pharmacophore model for 5-HT6 receptor antagonists (5-HT6R), we have designed and synthesized a novel series of benzopyran sulfonamide derivatives 9(a-d), 20(a-d) and 21(a-d) and their structures were confirmed by 1H NMR and mass spectral data. All the synthesized compounds were tested for their antagonistic activity towards 5-HT6R in a cell based reporter gene in vitro functional assay. Most of the tested compounds showed moderate to potent binding affinities towards 5-HT6R.
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- G. Rosse and H. Schaffhauser, Curr. Top. Med. Chem., 10, 207 (2010); doi:10.2174/156802610790411036.
- L.E. Hebert, L.A. Beckett, P.A. Scherr and D.A. Evans, Alzheimer Dis. Assoc. Disord., 15, 169 (2001); doi:10.1097/00002093-200110000-00002.
- M.R. Farlow and J.L. Cummings, Am. J. Med., 120, 388 (2007); doi:10.1016/j.amjmed.2006.08.036.
- D. Hoyer, D.E. Clarke, J.R. Fozard, P.R. Hartig, G.R. Martin, E. Mylecharane, P.R. Saxena and P.A. Humphrey, Pharmacol. Rev., 46, 157 (1994).
- R.P. Ward, M.W. Hamblin, J.E. Lachowicz, B.J. Hoffman, D.R. Sibley and D.M. Dorsa, Neuroscience, 64, 1105 (1995); doi:10.1016/0306-4522(94)00439-C.
- (a) L.A. Dawson, H.Q. Nguyen and P. Li, Neuropsychopharmacol., 25, 662 (2001); doi:10.1016/S0893-133X(01)00265-2; (b) L.A. Dawson, H.Q. Nguyen and P. Li, Br. J. Pharmacol., 130, 23 (2000); doi:10.1038/sj.bjp.0703288.
- T.A. Branchek and T.P. Blackburn, Annu. Rev. Pharmacol. Toxicol., 40, 319 (2000); doi:10.1146/annurev.pharmtox.40.1.319.
- S.L. Davies, J.S. Silvestre and X. Guitart, Drugs Future, 30, 479 (2005); doi:10.1358/dof.2005.030.05.907630.
- M.L. Lopez-Rodrıguez, B. Benhamú, T. de la Fuente, A. Sanz, L. Pardo and M. Campillo, J. Med. Chem., 48, 4216 (2005); doi:10.1021/jm050247c.
- 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, 1021 (2010); doi:10.1017/S1461145710000659.
- G. Maher-Edwards, R. Dixon, J. Hunter, M. Gold, G. Hopton, G. Jacobs, J. Hunter and P. Williams, Int. J. Geriatr. Psychiatry, 26, 536 (2011); doi:10.1002/gps.2562.
- R. Nirogi, V. Kandikere, K. Mudigonda, G. Bhyrapuneni and V. Jasti, Alzheimers Dement., 5, P250 (2009); doi:10.1016/j.jalz.2009.04.261.
- R. Nirogi, A. Shinde, A. Daulatabad, R. Kambhampati, P. Gudla, M. Shaik, M. Gampa, S. Balasubramaniam, P. Gangadasari, V. Reballi, R. Badange, K. Bojja, R. Subramanian, G. Bhyrapuneni, N. Muddana and P. Jayarajan, J. Med. Chem., 55, 9255 (2012); doi:10.1021/jm300955x.
- D.F.V. Lewis, Cytochromes P450: Structure, Function and Mechanism; Taylor and Francis Publishing: London (1996).
References
G. Rosse and H. Schaffhauser, Curr. Top. Med. Chem., 10, 207 (2010); doi:10.2174/156802610790411036.
L.E. Hebert, L.A. Beckett, P.A. Scherr and D.A. Evans, Alzheimer Dis. Assoc. Disord., 15, 169 (2001); doi:10.1097/00002093-200110000-00002.
M.R. Farlow and J.L. Cummings, Am. J. Med., 120, 388 (2007); doi:10.1016/j.amjmed.2006.08.036.
D. Hoyer, D.E. Clarke, J.R. Fozard, P.R. Hartig, G.R. Martin, E. Mylecharane, P.R. Saxena and P.A. Humphrey, Pharmacol. Rev., 46, 157 (1994).
R.P. Ward, M.W. Hamblin, J.E. Lachowicz, B.J. Hoffman, D.R. Sibley and D.M. Dorsa, Neuroscience, 64, 1105 (1995); doi:10.1016/0306-4522(94)00439-C.
(a) L.A. Dawson, H.Q. Nguyen and P. Li, Neuropsychopharmacol., 25, 662 (2001); doi:10.1016/S0893-133X(01)00265-2; (b) L.A. Dawson, H.Q. Nguyen and P. Li, Br. J. Pharmacol., 130, 23 (2000); doi:10.1038/sj.bjp.0703288.
T.A. Branchek and T.P. Blackburn, Annu. Rev. Pharmacol. Toxicol., 40, 319 (2000); doi:10.1146/annurev.pharmtox.40.1.319.
S.L. Davies, J.S. Silvestre and X. Guitart, Drugs Future, 30, 479 (2005); doi:10.1358/dof.2005.030.05.907630.
M.L. Lopez-Rodrıguez, B. Benhamú, T. de la Fuente, A. Sanz, L. Pardo and M. Campillo, J. Med. Chem., 48, 4216 (2005); doi:10.1021/jm050247c.
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, 1021 (2010); doi:10.1017/S1461145710000659.
G. Maher-Edwards, R. Dixon, J. Hunter, M. Gold, G. Hopton, G. Jacobs, J. Hunter and P. Williams, Int. J. Geriatr. Psychiatry, 26, 536 (2011); doi:10.1002/gps.2562.
R. Nirogi, V. Kandikere, K. Mudigonda, G. Bhyrapuneni and V. Jasti, Alzheimers Dement., 5, P250 (2009); doi:10.1016/j.jalz.2009.04.261.
R. Nirogi, A. Shinde, A. Daulatabad, R. Kambhampati, P. Gudla, M. Shaik, M. Gampa, S. Balasubramaniam, P. Gangadasari, V. Reballi, R. Badange, K. Bojja, R. Subramanian, G. Bhyrapuneni, N. Muddana and P. Jayarajan, J. Med. Chem., 55, 9255 (2012); doi:10.1021/jm300955x.
D.F.V. Lewis, Cytochromes P450: Structure, Function and Mechanism; Taylor and Francis Publishing: London (1996).