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Volumn 31, Issue , 2016, Pages 1-15

Synthesis and biological evaluation of novel N1-phenylsulphonyl indole derivatives as potent and selective 5-HT6R ligands for the treatment of cognitive disorders

Author keywords

5 Hydroxytryptamine 6 receptor; animal models; central nervous system; cognition; novel object recognition test; structure activity relationship

Indexed keywords

1 [4 METHYL 3 (4 METHYL PIPERAZIN 1 YL METHYL)PHENYLSULFONYL] 1H INDOLE; BENZENE DERIVATIVE; INDOLE DERIVATIVE; SEROTONIN 6 ANTAGONIST; SEROTONIN 6 RECEPTOR; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; 1-(4-METHYL-3-(4-METHYL PIPERAZIN-1-YL METHYL)PHENYLSULFONYL)-1H-INDOLE DIHYDROCHLORIDE; LIGAND; NEUROLEPTIC AGENT; PIPERAZINE DERIVATIVE; SEROTONIN RECEPTOR;

EID: 84994173166     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2015.1103233     Document Type: Article
Times cited : (2)

References (46)
  • 1
    • 0031949925 scopus 로고    scopus 로고
    • The cholinergic hypothesis of neuropsychiatric symptoms in Alzheimer's disease
    • Cummings JL, Back C. The cholinergic hypothesis of neuropsychiatric symptoms in Alzheimer's disease. Am J Geriatr Psychiatry 1998;6:S64–78
    • (1998) Am J Geriatr Psychiatry , vol.6 , pp. S64-S78
    • Cummings, J.L.1    Back, C.2
  • 2
    • 13544268496 scopus 로고    scopus 로고
    • Cholinergic-serotonergic imbalance contributes to cognitive and behavioral symptoms in Alzheimer's disease
    • Garcia-Alloza M, Gil-Bea FJ, Diez-Ariza M, et al. Cholinergic-serotonergic imbalance contributes to cognitive and behavioral symptoms in Alzheimer's disease. Neuropsychologia 2005;43:442–9
    • (2005) Neuropsychologia , vol.43 , pp. 442-449
    • Garcia-Alloza, M.1    Gil-Bea, F.J.2    Diez-Ariza, M.3
  • 3
    • 67649293283 scopus 로고    scopus 로고
    • Donepezil treatment of patients with MCI: a 48-week randomized, placebo-controlled trial
    • Doody RS, Ferris SH, Salloway S, et al. Donepezil treatment of patients with MCI:a 48-week randomized, placebo-controlled trial. Neurol 2009;72:1555–61
    • (2009) Neurol , vol.72 , pp. 1555-1561
    • Doody, R.S.1    Ferris, S.H.2    Salloway, S.3
  • 4
    • 34247232644 scopus 로고    scopus 로고
    • Effective pharmacologic management of Alzheimer's disease
    • Farlow MR, Cummings JL. Effective pharmacologic management of Alzheimer's disease. Am J Med 2007;120:388–97
    • (2007) Am J Med , vol.120 , pp. 388-397
    • Farlow, M.R.1    Cummings, J.L.2
  • 5
    • 70449732262 scopus 로고    scopus 로고
    • Update on the use of memantine in Alzheimer's disease
    • Van Marum RJ. Update on the use of memantine in Alzheimer's disease. Neuropsychiatr Dis Treat 2009;5:237–47
    • (2009) Neuropsychiatr Dis Treat , vol.5 , pp. 237-247
    • Van Marum, R.J.1
  • 6
    • 0030614562 scopus 로고    scopus 로고
    • 6 receptor-like material in the rat central nervous system
    • 6 receptor-like material in the rat central nervous system. Brain Res 1997;746:207–19
    • (1997) Brain Res , vol.746 , pp. 207-219
    • Gerard, C.1    Martres, M.P.2    Lefevre, K.3
  • 7
    • 0034782825 scopus 로고    scopus 로고
    • 6 receptor antagonist SB-271046 selectively enhances excitatory neurotransmission in the rat frontal cortex and hippocampus
    • 6 receptor antagonist SB-271046 selectively enhances excitatory neurotransmission in the rat frontal cortex and hippocampus. Neuropsychopharmacol 2001;25:662–8
    • (2001) Neuropsychopharmacol , vol.25 , pp. 662-668
    • Dawson, L.A.1    Nguyen, H.Q.2    Li, P.3
  • 8
    • 33751162382 scopus 로고    scopus 로고
    • 6 receptor antagonist with cognitive enhancing properties in aged rat water maze and novel object recognition models
    • 6 receptor antagonist with cognitive enhancing properties in aged rat water maze and novel object recognition models. Eur J Pharmacol 2006;553:109–19
    • (2006) Eur J Pharmacol , vol.553 , pp. 109-119
    • Hirst, W.D.1    Stean, T.O.2    Rogers, D.C.3
  • 9
    • 84901826580 scopus 로고    scopus 로고
    • Serotonergic therapies for cognitive symptoms in Alzheimer's disease: rationale and current status
    • Ramirez MJ, Lai MKP, Tordera RM, Francis PT. Serotonergic therapies for cognitive symptoms in Alzheimer's disease:rationale and current status. Drugs 2014;74:729–36
    • (2014) Drugs , vol.74 , pp. 729-736
    • Ramirez, M.J.1    Lai, M.K.P.2    Tordera, R.M.3    Francis, P.T.4
  • 11
    • 84997622779 scopus 로고    scopus 로고
    • Biotie therapies. Available from: [last accessed 1 May 2015]
    • Biotie therapies. Available from:http://www.biotie.com/en/product_and_development/development_pipeline/syn120 [last accessed 1 May 2015]
  • 12
    • 84997786494 scopus 로고    scopus 로고
    • Pfizer. Available from: & pain [last accessed 1 May 2015]
    • Pfizer. Available from:http://www.pfizer.com/sites/default/files/productpipeline/pipeline_2013_0509.pdf/Neuroscience & pain [last accessed 1 May 2015]
  • 13
    • 84997652098 scopus 로고    scopus 로고
    • Avineuro Pharmaceuticals. Available from: [last accessed 1 May 2015]
    • Avineuro Pharmaceuticals. Available from:http://www.biocentury.com/products/avn-211 [last accessed 1 May 2015]
  • 14
    • 77957240422 scopus 로고    scopus 로고
    • 6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol 2010;13:1021–33
    • 6 antagonist, reverses cognitive impairment induced by subchronic phencyclidine in a novel object recognition test in rats. Int J Neuropsychopharmacol 2010;13:1021–33
  • 15
    • 84997786491 scopus 로고    scopus 로고
    • GlaxoSmithKline
    • GlaxoSmithKline. Available from:http://www.gsk.com/research/our-product-pipeline.html [last accessed 1 May 2015]
  • 16
    • 82555185519 scopus 로고    scopus 로고
    • 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
    • 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
    • (2011) J Med Chem , vol.54 , pp. 8161-8173
    • Ivachtchenko, A.V.1    Golovina, E.S.2    Kadieva, M.G.3
  • 17
    • 77954744296 scopus 로고    scopus 로고
    • 3-Phenylsulfonylcycloalkano[e and d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: potent and selective antagonists of the serotonin 5-HT6 receptor
    • 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
    • (2010) J Med Chem , vol.53 , pp. 5186-5196
    • Ivachtchenko, A.V.1    Dmitriev, D.E.2    Golovina, E.S.3
  • 18
    • 84862234229 scopus 로고    scopus 로고
    • 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
    • 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
    • (2012) Bioorg Med Chem Lett , vol.22 , pp. 4273-4280
    • Ivachtchenko, A.V.1    Golovina, E.S.2    Kadieva, M.G.3
  • 19
    • 79951554164 scopus 로고    scopus 로고
    • Synthesis and SAR of 3-arylsulfonyl-pyrazolo[1,5-a]pyrimidines as potent serotonin 5-HT6 receptor antagonists
    • 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
    • (2011) Bioorg Med Chem , vol.19 , pp. 1482-1491
    • Ivachtchenko, A.V.1    Golovina, E.S.2    Kadieva, M.G.3
  • 20
    • 79952283346 scopus 로고    scopus 로고
    • 2-Substituted 5,6-dimethyl-3-phenylsulfonyl-pyrazolo[1,5-a]pyrimidines: new series of highly potent and specific serotonin 5-HT6 receptor antagonists
    • 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
    • (2011) Eur J Med Chem , vol.46 , pp. 1189-1197
    • Ivachtchenko, A.V.1    Golovina, E.S.2    Kadieva, M.G.3
  • 21
    • 0034624773 scopus 로고    scopus 로고
    • (a) Glennon RA. Higher-end serotonin receptors:5-HT(5), 5-HT(6), and 5-HT(7). J Med Chem 2003;4:2795–812. (b) 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
    • (2000) J Med Chem , vol.43 , pp. 1011-1018
  • 22
    • 78149278323 scopus 로고    scopus 로고
    • 5Piperazinyl-3-sulfonylindazoles as potent and selective 5-hydroxytryptamine-6 antagonists
    • Liu KG, Robichaud AJ, Bernotas RC, et al. 5Piperazinyl-3-sulfonylindazoles as potent and selective 5-hydroxytryptamine-6 antagonists. J Med Chem 2010;53:7639–46
    • (2010) J Med Chem , vol.53 , pp. 7639-7646
    • Liu, K.G.1    Robichaud, A.J.2    Bernotas, R.C.3
  • 23
    • 0033854822 scopus 로고    scopus 로고
    • Characterization of SB-271046: a potent, selective and orally active 5-HT(6) receptor antagonist
    • Routledge C, Bromidge SM, Moss SF, et al. Characterization of SB-271046:a potent, selective and orally active 5-HT(6) receptor antagonist. Br J Pharmacol 2000;130:1606–12
    • (2000) Br J Pharmacol , vol.130 , pp. 1606-1612
    • Routledge, C.1    Bromidge, S.M.2    Moss, S.F.3
  • 25
    • 50249139121 scopus 로고    scopus 로고
    • 6 receptor antagonists: prospects for the treatment of cognitive disorders including dementia
    • 6 receptor antagonists:prospects for the treatment of cognitive disorders including dementia. Curr Opin Drug Discov Devel 2008;11:642–54
    • (2008) Curr Opin Drug Discov Devel , vol.11 , pp. 642-654
    • Johnson, C.N.1    Ahmed, M.2    Miller, N.D.3
  • 28
    • 19944430163 scopus 로고    scopus 로고
    • 6 antagonists as potential treatment for cognitive dysfunction. J Drug Dev Res 2009;70:145–68. (c) Beard CC, Clark RD, Fisher LM, et al. US Patent 0073700 A1; 2003
    • (2003) US Patent , vol.73700 , pp. A1
    • Beard, C.1    Clark, R.2    Fisher, L.3
  • 29
    • 84920128903 scopus 로고    scopus 로고
    • 6 receptor antagonists for the treatment of cognitive deficiency in Alzheimer’s disease
    • 6 receptor antagonists for the treatment of cognitive deficiency in Alzheimer’s disease. J Med Chem 2014;57:7160–81
    • (2014) J Med Chem , vol.57 , pp. 7160-7181
    • Benhamú, B.1    Martín-Fontecha, M.2    Vázquez-Villa, H.3
  • 30
    • 77955432030 scopus 로고    scopus 로고
    • Synthesis and pharmacological evaluation of aryl aminosulfonamide derivatives as potent 5-HT(6) receptor antagonists
    • Nirogi R, Daulatabad A, Parandhama G, et al. Synthesis and pharmacological evaluation of aryl aminosulfonamide derivatives as potent 5-HT(6) receptor antagonists. Bioorg Med Chem Lett 2010;20:4440–3
    • (2010) Bioorg Med Chem Lett , vol.20 , pp. 4440-4443
    • Nirogi, R.1    Daulatabad, A.2    Parandhama, G.3
  • 31
    • 79960352440 scopus 로고    scopus 로고
    • Rigidized 1-aryl sulfonyl tryptamines: synthesis and pharmacological evaluation as 5-HT6 receptor ligands
    • Nirogi R, Dwarampudi A, Kambhampati R, et al. Rigidized 1-aryl sulfonyl tryptamines:synthesis and pharmacological evaluation as 5-HT6 receptor ligands. Bioorg Med Chem Lett 2011;21:4577–80
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 4577-4580
    • Nirogi, R.1    Dwarampudi, A.2    Kambhampati, R.3
  • 34
    • 84879694862 scopus 로고    scopus 로고
    • Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-НТ6 receptors
    • Ivachtchenko A, Golovina E, Kadieva M, et al. Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-НТ6 receptors. Bioorg Med Chem 2013;21:4614–27
    • (2013) Bioorg Med Chem , vol.21 , pp. 4614-4627
    • Ivachtchenko, A.1    Golovina, E.2    Kadieva, M.3
  • 37
    • 0033624158 scopus 로고    scopus 로고
    • Characterization of [(125)I]-SB-258585 binding to human recombinant and native 5-HT(6) receptors in rat, pig and human brain tissue
    • Hirst WD, Minton JA, Bromidge SM, et al. Characterization of [(125)I]-SB-258585 binding to human recombinant and native 5-HT(6) receptors in rat, pig and human brain tissue. Br J Pharmacol 2000;130:1597–605
    • (2000) Br J Pharmacol , vol.130 , pp. 1597-1605
    • Hirst, W.D.1    Minton, J.A.2    Bromidge, S.M.3
  • 39
  • 41
    • 38549144692 scopus 로고    scopus 로고
    • 6 receptor ligands: progress in the development of a novel pharmacological approach to the treatment of obesity and related metabolic disorders
    • 6 receptor ligands:progress in the development of a novel pharmacological approach to the treatment of obesity and related metabolic disorders. Pharmacol Ther 2008;17:207–31
    • (2008) Pharmacol Ther , vol.17 , pp. 207-231
    • Heal, D.J.1    Smith, S.L.2    Fisas, A.3
  • 46
    • 0030683616 scopus 로고    scopus 로고
    • The effects of neurotoxic lesions of the perirhinal cortex combined to fornix transection on object recognition memory in the rat
    • Ennaceur A, Neave N, Aggleton JP. The effects of neurotoxic lesions of the perirhinal cortex combined to fornix transection on object recognition memory in the rat. Behav Brain Res 1997;88:181–93
    • (1997) Behav Brain Res , vol.88 , pp. 181-193
    • Ennaceur, A.1    Neave, N.2    Aggleton, J.P.3


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