Design, synthesis and pharmacological evaluation of indolylsulfonamide amines as potent and selective 5-HT₆ receptor antagonists

References

• ADI/WHO. World Health Organization and Alzheimer’s Disease International say dementia must be a global health priority, Geneva. News Release/11-Apr-2012. Available from: http://www.alz.co.uk [last accessed 21 Jun 2013]
   Google Scholar
• Roth BL, Lopez E, Patel S, Kroeze WK. Neuronal signal transduction pathways. Neuroscientist 2000;6:252–62
   Web of Science ®Google Scholar
• Hoyer D, Hannon JP. Molecular, pharmacological and functional diversity of 5-HT receptors. Pharmacol Biochem Behav 2002;71:533–54
   PubMed Web of Science ®Google Scholar
• Jones BJ, Blackburn TP. The medical benefit of 5-HT research. Pharmacol Biochem Behav 2002;71:555–68
   PubMed Web of Science ®Google Scholar
• Bikker JA, Trump-Kallmeyer S, Humblet S. G-protein coupled receptors: models, mutagenesis, and drug design. J Med Chem 1998;41:2911–27
   PubMed Web of Science ®Google Scholar
• Sebben M, Ansanay H, Bockaert J, Dumuis A. 5-HT6 receptors positively coupled to adenylyl cyclase in striatal neurones in culture. Neuroreport 1994;5:2553–7
   PubMed Web of Science ®Google Scholar
• Arnt J, Olsen CK. 5-HT6 receptor ligands and their antipsychotic potential. Int Rev Neurobiol 2011;96:141–61
   PubMed Web of Science ®Google Scholar
• Roth BL, Craigo SC, Choudhary MS, et al. Binding of typical and atypical antipsychotic agents to 5-hydroxytryptamine-6 and 5-hydroxytryptamine-7 receptors. J Pharmacol Exp Ther 1994;268:1403–10
   PubMed Web of Science ®Google Scholar
• Shinkai T, Ohmori O, Kojima H, et al. Association study of the 5-HT6 receptor gene in schizophrenia. Am J Med Genet 1999;88:120–2
   PubMed Web of Science ®Google Scholar
• Tsai SJ, Chiu HJ, Wang YC, Hong CJ. Association study of serotonin-6 receptor variant (C267T) with schizophrenia and aggressive behavior. Neurosci Lett 1999;271:135–7
   PubMed Web of Science ®Google Scholar
• Vogt IR, Shimron-Abarbanell D, Neidt H, et al. Investigation of the human serotonin 6 [5-HT6] receptor gene in bipolar affective disorder and schizophrenia. Am J Med Genet 2000;96:217–21
   PubMed Web of Science ®Google Scholar
• Ohmori O, Shinkai T, Hori H, Nakamura J. Novel polymorphism in the 50-upstream region of the human 5-HT6 receptor gene and schizophrenia. Neurosci Lett 2001;310:17–20
   PubMed Web of Science ®Google Scholar
• East SZ, Burnet PW, Leslie RA, et al. 5-HT6 receptor binding sites in schizophrenia and following antipsychotic drug administration: autoradiographic studies with [125I]SB-258585. Synapse 2002;45:191–9
   PubMed Web of Science ®Google Scholar
• Wu WH, Huo SJ, Cheng CY, et al. Association study of the 5-HT6 receptor polymorphism (C267T) and symptomatology and antidepressant response in major depressive disorders. Neuropsychobiology 2001;44:172–5
   PubMed Web of Science ®Google Scholar
• Messina D, Annesi G, Serra P, et al. Association of the 5-HT6 receptor gene polymorphism C267T with Parkinson’s disease. Neurology 2002;58:828–9
   PubMed Web of Science ®Google Scholar
• Thome J, Retz W, Baader M, et al. Association analysis of HTR6 and HTR2A polymorphisms in sporadic Alzheimer’s disease. J Neural Transm 2001;108:1175–80
   PubMed Web of Science ®Google Scholar
• Liu HC, Hong CJ, Liu CY, et al. Association analysis of the 5-HT6 receptor polymorphism C267T with depression in patients with Alzheimer’s disease. Psychiatry Clin Neurosci 2001;55:427–9
   PubMed Web of Science ®Google Scholar
• Garcia-Alloza M, Hirst WD, Chen CP, et al. Differential involvement of 5-HT1B/1D and 5-HT6 receptors in cognitive and non-cognitive symptoms in Alzheimer’s disease. Neuropsychopharmacology 2004;29:410–16
   PubMed Web of Science ®Google Scholar
• Glennon RA. Higher-end serotonin receptors: 5-HT(5), 5-HT(6), and 5-HT(7). J Med Chem 2003;46:2795–812
   PubMed Web of Science ®Google Scholar
• Holenz J, Pauwels PJ, Díaz JL, et al. Medicinal chemistry strategies to 5-HT(6) receptor ligands as potential cognitive enhancers and antiobesity agents. Drug Discov Today 2006;1:283–99
   Google Scholar
• Liu KG, Robichaud AJ. 5-HT6 antagonists as potential treatment for cognitive dysfunction. Drug Develop Res 2009;70:145–68
   Web of Science ®Google Scholar
• Available from: http://www.pfizer.com/sites/default/files/product-pipeline/pipeline_2013_0509.pdf/Neuroscience & pain [last accessed 21 Jun 2013]
   Google Scholar
• Available from: http://www.gsk.com/research/our-product-pipeline.html [last accessed 21 Jun 2013]
   Google Scholar
• Available from: http://www.biocentury.com/products/avn-211 [last accessed 21 Jun 2013]
   Google Scholar
• Ivachtchenko AV, Savchuk NP, Ivachtchenko AA. Substituted 4-sulphonyl-pyrazoles and 3-sulphonyl-pyrazolo[1,5-a]pyrimidines-antagonists of serotonin 5-HT6 receptors, active component, pharmaceutical composition, medicinal agent and method of obtaining them. RU Patent 2369600; 2009
   Google Scholar
• Ivachtchenko AV, Savchuk NP, Ivachtchenko AA. 3-Sulfonyl-pyrazolo[1,5-a] pyrimidines/antagonists of serotonin 5-ht6 receptors, methods for the production and the use thereof. WO Patent 093206; 2009
   Google Scholar
• Lundbeck. Lundbeck’s Lu AE58054 meets primary endpoint in large placebo-controlled clinical proof of concept study in people with Alzheimer’s disease. Corporate Releases/29-May-2012. Available from: http://www.lundbeck.com/global [last accessed 02 Apr 2013]
   Google Scholar
• Jorn A, Benny B, Ben G, et al. Lu AE58054, a 5-HT6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol 2010;13:1021–33
   PubMed Web of Science ®Google Scholar
• Available from: http://www.biotie.com/en/product_and_development/development_pipeline/syn120 [last accessed 21 Jun 2013]
   Google Scholar
• Nirogi R, Kambhampati R, Shinde A, et al. 12th International Conference on Alzheimer’s disease; 2009; Vienna
   Google Scholar
• Glennon RA, Lee M, Rangisetty JB, et al. 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors. J Med Chem 2000;43:1011–18
   PubMed Web of Science ®Google Scholar
• Kambhampati R, Konda J, Reballi V, et al. Design, synthesis and preliminary screening of novel 3-(2-N,N-dimethylaminoethylthio) indole derivatives as potential 5-HT6 receptor ligands. J Enz Inhib Med Chem 2008;23:302–12
   PubMed Web of Science ®Google Scholar
• Nirogi RVS, Kambhampati R, Daulatabad AV, et al. Design, synthesis and pharmacological evaluation of conformationally restricted N-arylsulfonyl-3-aminoalkoxy indoles as a potential 5-HT6 receptor ligands. J Enz Inhib Med Chem 2011;26:341–9
   PubMed Web of Science ®Google Scholar
• Davies SL, Silvestre JS, Guitart X. Drug discovery targets: 5-HT6 receptor. Drugs of the Future 2005;30:479–95
   Web of Science ®Google Scholar
• Kim HJ, Doddareddy MR, Choo H, et al. New serotonin 5-HT6 ligands from common feature pharmacophore. Hypotheses. J Chem Inf Model 2008;48:197–206
   PubMed Web of Science ®Google Scholar
• Nirogi RVS, Kambhampati R, Kothmirkar P, et al. Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands. J Enz Inhib Med Chem 2012;27:443–50
   PubMed Web of Science ®Google Scholar
• Ivachtchenko A, Golovina E, Kadieva M, et al. Synthesis of substituted diphenyl sulfones and their structure–activity relationship with the antagonism of 5-HT6 receptors. Bioorg Med Chem 2013;21:4614–27
   PubMed Web of Science ®Google Scholar
• Ivachtchenko AV, Golovina ES, Kadieva MG, et al. Synthesis and structure–activity relationship (SAR) of (5,7-disubstituted 3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidin-2-yl)-methylamines as potent serotonin 5-HT6 receptor (5-HT6R) antagonists. J Med Chem 2011;54:8161–73
   PubMed Web of Science ®Google Scholar
• Ivachtchenko AV, Dmitriev DE, Golovina ES, et al. (3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: potent and selective antagonists of the serotonin 5-HT6 receptor. J Med Chem 2010;53:5186–96
   PubMed Web of Science ®Google Scholar
• Ivachtchenko AV, Golovina ES, Kadieva MG, et al. Antagonists of 5-HT6 receptors. Substituted 3-(phenylsulfonyl) pyrazolo[1,5-a]pyrido[3,4-e]pyrimidines and 3-(phenylsulfonyl) pyrazolo[1,5-a]pyrido[4,3-d]pyrimidines – synthesis and ‘structure–activity’ relationship. Bioorg Med Chem Lett 2012;22:4273–80
   PubMed Web of Science ®Google Scholar
• Ivachtchenko AV, Golovina ES, Kadieva MG, et al. Synthesis and SAR of 3-arylsulfonyl-pyrazolo[1,5-a]pyrimidines as potent serotonin 5-HT6 receptor antagonists. Bioorg Med Chem 2011;19:1482–91
   PubMed Web of Science ®Google Scholar
• Ivachtchenko AV, Golovina ES, Kadieva MG, et al. 2-Substituted 5,6-dimethyl-3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines: new series of highly potent and specific serotonin 5-HT6 receptor antagonists. Eur J Med Chem 2011;46:1189–97
   PubMed Web of Science ®Google Scholar
• Lopez-Rodriguez ML, Benhamu B, Fuente T, et al. A three-dimensional pharmacophore model for 5-hydroxytryptamine6 (5-HT6) receptor antagonists. J Med Chem 2005;48:4216–19
   PubMed Web of Science ®Google Scholar
• Bromidge SM. Potent and selective 5-HT6 receptor antagonists. Spec Publ – R Soc Chem 2001;264:101–19
   Google Scholar
• Hirst WD, Minton JA, Bromidge SM, et al. Characterization of [125I]-SB-258585 binding to human recombinant and native 5-HT6 receptors in rat, pig and human brain tissue. Br J Pharmacol 2000;130:1597–605
   PubMed Web of Science ®Google Scholar
• Pullagurla MR, Westkaemper RB, Glennon RA. Possible differences in modes of binding of agonist and antagonist binding at human 5-HT6 receptors. Bioorg Med Chem Lett 2004;14:4569–73
   PubMed Web of Science ®Google Scholar
• Dukat M, Mosier PD, Kolanos R, et al. Binding of serotonin and N1-benzenesulfonyltryptamine-related analogs at human 5-HT6 serotonin receptors: receptor modeling studies. J Med Chem 2008;51:603–11
   PubMed Web of Science ®Google Scholar
• Sikazwe D, Bondarev ML, Dukat M, et al. Binding of sulfonyl-containing arylalkylamines at human 5-HT6 serotonin receptors. J Med Chem 2006;49:5217–25
   PubMed Web of Science ®Google Scholar
• Heal DJ, Smith SL, Fisas A, et al. Selective 5-HT6 receptor ligands: progress in the development of a novel pharmacological approach to the treatment of obesity and related metabolic disorders. Pharmacol Therapeutics 2008;17:207–31
   Web of Science ®Google Scholar
• Kohen R, Fashingbauer LA, Heidmann DE, et al. Cloning of the mouse 5-HT6 serotonin receptor and mutagenesis studies of the third cytoplasmic loop. Brain Res Mol Brain Res 2001;90:110–17
   PubMedGoogle Scholar
• Gonzalo R, Elisabeth S, Marta P, et al. Efficacy of selective 5-HT6 receptor ligands determined by monitoring 5-HT6 receptor-mediated cAMP signaling pathways. Br J Pharmacol 2006;148:1133–43
   PubMed Web of Science ®Google Scholar