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Volumn 55, Issue 12, 2012, Pages 5826-5840

Structure-activity relationship study of N 6-(2-(4-(1 H -Indol-5-yl)piperazin-1-yl)ethyl)- N 6-propyl-4,5,6,7- tetrahydrobenzo[ d ]thiazole-2,6-diamine analogues: Development of highly selective D3 dopamine receptor agonists along with a highly potent D2/D3 agonist and their pharmacological characterization

Author keywords

[No Author keywords available]

Indexed keywords

BENZOXONIUM CHLORIDE; DIAMINE DERIVATIVE; DOPAMINE 2 RECEPTOR STIMULATING AGENT; DOPAMINE 3 RECEPTOR STIMULATING AGENT; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); N6 [2 [4 (1H INDOL 5 YL)PIPERAZIN 1 YL]ETHYL] N6 PROPYL 4,5,6,7 TETRAHYDROBENZO[D]THIAZOLE 2,6 DIAMINE DERIVATIVE; ROPINIROLE; SPIPERONE; UNCLASSIFIED DRUG;

EID: 84863096828     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300268s     Document Type: Article
Times cited : (46)

References (44)
  • 1
    • 0018378511 scopus 로고
    • Multiple receptors for dopamine
    • Kebabian, J. W.; Calne, D. B. Multiple receptors for dopamine Nature 1979, 277, 93-96
    • (1979) Nature , vol.277 , pp. 93-96
    • Kebabian, J.W.1    Calne, D.B.2
  • 2
    • 0025605252 scopus 로고
    • Gene cloning of human dopaminergic D3 receptor and identification of its chromosome
    • Giros, B.; Martres, M. P.; Sokoloff, P.; Schwartz, J. C. Gene cloning of human dopaminergic D3 receptor and identification of its chromosome C. R. Acad. Sci., Ser. III 1990, 311, 501-508
    • (1990) C. R. Acad. Sci., Ser. III , vol.311 , pp. 501-508
    • Giros, B.1    Martres, M.P.2    Sokoloff, P.3    Schwartz, J.C.4
  • 3
    • 0025179967 scopus 로고
    • Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics
    • Sokoloff, P.; Giros, B.; Martres, M. P.; Bouthenet, M. L.; Schwartz, J. C. Molecular cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics Nature 1990, 347, 146-151
    • (1990) Nature , vol.347 , pp. 146-151
    • Sokoloff, P.1    Giros, B.2    Martres, M.P.3    Bouthenet, M.L.4    Schwartz, J.C.5
  • 4
    • 0026427253 scopus 로고
    • Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine
    • Van Tol, H. H.; Bunzow, J. R.; Guan, H. C.; Sunahara, R. K.; Seeman, P.; Niznik, H. B.; Civelli, O. Cloning of the gene for a human dopamine D4 receptor with high affinity for the antipsychotic clozapine Nature 1991, 350, 610-614
    • (1991) Nature , vol.350 , pp. 610-614
    • Van Tol, H.H.1    Bunzow, J.R.2    Guan, H.C.3    Sunahara, R.K.4    Seeman, P.5    Niznik, H.B.6    Civelli, O.7
  • 6
    • 0027401068 scopus 로고
    • New insights into dopamine receptors in the central nervous system
    • Strange, P. G. New insights into dopamine receptors in the central nervous system Neurochem. Int. 1993, 22, 223-236
    • (1993) Neurochem. Int. , vol.22 , pp. 223-236
    • Strange, P.G.1
  • 8
    • 0032589813 scopus 로고    scopus 로고
    • Distribution of dopamine D3 receptor expressing neurons in the human forebrain: Comparison with D2 receptor expressing neurons
    • Gurevich, E. V.; Joyce, J. N. Distribution of dopamine D3 receptor expressing neurons in the human forebrain: comparison with D2 receptor expressing neurons Neuropsychopharmacology 1999, 20, 60-80
    • (1999) Neuropsychopharmacology , vol.20 , pp. 60-80
    • Gurevich, E.V.1    Joyce, J.N.2
  • 9
    • 0032829657 scopus 로고    scopus 로고
    • Dopamine receptors: Physiological understanding to therapeutic intervention potential
    • Emilien, G.; Maloteaux, J. M.; Geurts, M.; Hoogenberg, K.; Cragg, S. Dopamine receptors: physiological understanding to therapeutic intervention potential Pharmacol. Ther. 1999, 84, 133-156
    • (1999) Pharmacol. Ther. , vol.84 , pp. 133-156
    • Emilien, G.1    Maloteaux, J.M.2    Geurts, M.3    Hoogenberg, K.4    Cragg, S.5
  • 10
    • 33748032418 scopus 로고    scopus 로고
    • The structural evolution of dopamine D3 receptor ligands: Structure-activity relationships and selected neuropharmacological aspects
    • Boeckler, F.; Gmeiner, P. The structural evolution of dopamine D3 receptor ligands: structure-activity relationships and selected neuropharmacological aspects Pharmacol. Ther. 2006, 112, 281-333
    • (2006) Pharmacol. Ther. , vol.112 , pp. 281-333
    • Boeckler, F.1    Gmeiner, P.2
  • 11
    • 0028795231 scopus 로고
    • Structural organization of the murine D3 dopamine receptor gene
    • Park, B. H.; Fishburn, C. S.; Carmon, S.; Accili, D.; Fuchs, S. Structural organization of the murine D3 dopamine receptor gene J. Neurochem. 1995, 64, 482-486
    • (1995) J. Neurochem. , vol.64 , pp. 482-486
    • Park, B.H.1    Fishburn, C.S.2    Carmon, S.3    Accili, D.4    Fuchs, S.5
  • 12
    • 0026076047 scopus 로고
    • The neuropathologic basis of different clinical subgroups of Parkinson's disease
    • Paulus, W.; Jellinger, K. The neuropathologic basis of different clinical subgroups of Parkinson's disease J. Neuropathol. Exp. Neurol. 1991, 50, 743-755
    • (1991) J. Neuropathol. Exp. Neurol. , vol.50 , pp. 743-755
    • Paulus, W.1    Jellinger, K.2
  • 15
    • 0037378026 scopus 로고    scopus 로고
    • Oxidative stress in Parkinson's disease
    • discussion S36-S88
    • Jenner, P. Oxidative stress in Parkinson's disease Ann. Neurol. 2003, 53 (Suppl. 3) S26-S36; discussion S36-S88
    • (2003) Ann. Neurol. , vol.53 , Issue.SUPPL. 3
    • Jenner, P.1
  • 16
    • 0242363670 scopus 로고    scopus 로고
    • Molecular pathways of neurodegeneration in Parkinson's disease
    • Dawson, T. M.; Dawson, V. L. Molecular pathways of neurodegeneration in Parkinson's disease Science 2003, 302, 819-822
    • (2003) Science , vol.302 , pp. 819-822
    • Dawson, T.M.1    Dawson, V.L.2
  • 18
    • 0026662216 scopus 로고
    • Biochemical and toxicological properties of the oxidation products of catecholamines
    • Bindoli, A.; Rigobello, M. P.; Deeble, D. J. Biochemical and toxicological properties of the oxidation products of catecholamines Free Radical Biol. Med. 1992, 13, 391-405
    • (1992) Free Radical Biol. Med. , vol.13 , pp. 391-405
    • Bindoli, A.1    Rigobello, M.P.2    Deeble, D.J.3
  • 19
    • 0017275668 scopus 로고
    • "On-off" effects in patients with Parkinson's disease on chronic levodopa therapy
    • Marsden, C. D.; Parkes, J. D. "On-off" effects in patients with Parkinson's disease on chronic levodopa therapy Lancet 1976, 1, 292-296
    • (1976) Lancet , vol.1 , pp. 292-296
    • Marsden, C.D.1    Parkes, J.D.2
  • 21
    • 0032936755 scopus 로고    scopus 로고
    • Etiology and pathogenesis of Parkinson's disease
    • Olanow, C. W.; Tatton, W. G. Etiology and pathogenesis of Parkinson's disease Annu. Rev. Neurosci. 1999, 22, 123-144
    • (1999) Annu. Rev. Neurosci. , vol.22 , pp. 123-144
    • Olanow, C.W.1    Tatton, W.G.2
  • 22
    • 0036278335 scopus 로고    scopus 로고
    • Dopamine-dependent neurotoxicity of alpha-synuclein: A mechanism for selective neurodegeneration in Parkinson disease
    • Xu, J.; Kao, S. Y.; Lee, F. J.; Song, W.; Jin, L. W.; Yankner, B. A. Dopamine-dependent neurotoxicity of alpha-synuclein: a mechanism for selective neurodegeneration in Parkinson disease Nat. Med. 2002, 8, 600-606
    • (2002) Nat. Med. , vol.8 , pp. 600-606
    • Xu, J.1    Kao, S.Y.2    Lee, F.J.3    Song, W.4    Jin, L.W.5    Yankner, B.A.6
  • 24
    • 36248929304 scopus 로고    scopus 로고
    • Disruption of dopamine homeostasis underlies selective neurodegeneration mediated by alpha-synuclein
    • Park, S. S.; Schulz, E. M.; Lee, D. Disruption of dopamine homeostasis underlies selective neurodegeneration mediated by alpha-synuclein Eur. J. Neurosci. 2007, 26, 3104-3112
    • (2007) Eur. J. Neurosci. , vol.26 , pp. 3104-3112
    • Park, S.S.1    Schulz, E.M.2    Lee, D.3
  • 27
    • 0037154184 scopus 로고    scopus 로고
    • Recent advances in the genetics and pathogenesis of Parkinson disease
    • Mouradian, M. M. Recent advances in the genetics and pathogenesis of Parkinson disease Neurology 2002, 58, 179-185
    • (2002) Neurology , vol.58 , pp. 179-185
    • Mouradian, M.M.1
  • 28
    • 3242815390 scopus 로고    scopus 로고
    • Synthesis and biological characterization of novel hybrid 7-[[2-(4-phenyl-piperazin-1-yl)-ethyl]-propyl-amino]-5,6,7,8-tetrahydro- naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors
    • Dutta, A. K.; Venkataraman, S. K.; Fei, X. S.; Kolhatkar, R.; Zhang, S.; Reith, M. E. Synthesis and biological characterization of novel hybrid 7-[[2-(4-phenyl-piperazin-1-yl)-ethyl]-propyl-amino]-5,6,7,8-tetrahydro- naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors Bioorg. Med. Chem. 2004, 12, 4361-4373
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 4361-4373
    • Dutta, A.K.1    Venkataraman, S.K.2    Fei, X.S.3    Kolhatkar, R.4    Zhang, S.5    Reith, M.E.6
  • 29
    • 43949101004 scopus 로고    scopus 로고
    • Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl) ethyl]propylamino}-5,6,7,8-tetrahydronaphth alen-2-ol: Identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity
    • Biswas, S.; Hazeldine, S.; Ghosh, B.; Parrington, I.; Kuzhikandathil, E.; Reith, M. E.; Dutta, A. K. Bioisosteric heterocyclic versions of 7-{[2-(4-phenyl-piperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphth alen-2-ol: identification of highly potent and selective agonists for dopamine D3 receptor with potent in vivo activity J. Med. Chem. 2008, 51, 3005-3019
    • (2008) J. Med. Chem. , vol.51 , pp. 3005-3019
    • Biswas, S.1    Hazeldine, S.2    Ghosh, B.3    Parrington, I.4    Kuzhikandathil, E.5    Reith, M.E.6    Dutta, A.K.7
  • 30
    • 37849011620 scopus 로고    scopus 로고
    • Further structure-activity relationships study of hybrid 7-{[2-(4-phenylpiperazin-1-yl)ethyl]propylamino}-5,6,7,8-tetrahydronaphthalen-2- ol analogues: Identification of a high-affinity D3-preferring agonist with potent in vivo activity with long duration of action
    • Biswas, S.; Zhang, S.; Fernandez, F.; Ghosh, B.; Zhen, J.; Kuzhikandathil, E.; Reith, M. E.; Dutta, A. K. Further structure-activity relationships study of hybrid 7-{[2-(4-phenylpiperazin-1-yl)ethyl]propylamino}- 5,6,7,8-tetrahydronaphthalen-2-ol analogues: identification of a high-affinity D3-preferring agonist with potent in vivo activity with long duration of action J. Med. Chem. 2008, 51, 101-117
    • (2008) J. Med. Chem. , vol.51 , pp. 101-117
    • Biswas, S.1    Zhang, S.2    Fernandez, F.3    Ghosh, B.4    Zhen, J.5    Kuzhikandathil, E.6    Reith, M.E.7    Dutta, A.K.8
  • 31
    • 77949421702 scopus 로고    scopus 로고
    • Discovery of 4-(4-(2-((5-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl) (propyl)amino)ethyl) piperazin-1-yl)quinolin-8-ol and its analogues as highly potent dopamine D2/D3 agonists and as iron chelator: In vivo activity indicates potential application in symptomatic and neuroprotective therapy for Parkinson's disease
    • Ghosh, B.; Antonio, T.; Reith, M. E.; Dutta, A. K. Discovery of 4-(4-(2-((5-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)ethyl) piperazin-1-yl)quinolin-8-ol and its analogues as highly potent dopamine D2/D3 agonists and as iron chelator: in vivo activity indicates potential application in symptomatic and neuroprotective therapy for Parkinson's disease J. Med. Chem. 2010, 53, 2114-2125
    • (2010) J. Med. Chem. , vol.53 , pp. 2114-2125
    • Ghosh, B.1    Antonio, T.2    Reith, M.E.3    Dutta, A.K.4
  • 32
    • 65549122009 scopus 로고    scopus 로고
    • Investigation of various N-heterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro- naphthalen-2-ol: Effect on affinity and selectivity for dopamine D3 receptor
    • Brown, D. A.; Mishra, M.; Zhang, S.; Biswas, S.; Parrington, I.; Antonio, T.; Reith, M. E.; Dutta, A. K. Investigation of various N-heterocyclic substituted piperazine versions of 5/7-{[2-(4-aryl-piperazin-1-yl)-ethyl]- propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol: effect on affinity and selectivity for dopamine D3 receptor Bioorg. Med. Chem. 2009, 17, 3923-3933
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 3923-3933
    • Brown, D.A.1    Mishra, M.2    Zhang, S.3    Biswas, S.4    Parrington, I.5    Antonio, T.6    Reith, M.E.7    Dutta, A.K.8
  • 33
    • 77249109359 scopus 로고    scopus 로고
    • Development of (S)- N 6-(2-(4-(isoquinolin-1-yl)piperazin-1-yl)ethyl)- N 6-propyl-4,5,6,7-tetrahydrobenzo[ d ]-thiazole-2,6-diamine and its analogue as a D3 receptor preferring agonist: Potent in vivo activity in Parkinson's disease animal models
    • Ghosh, B.; Antonio, T.; Zhen, J.; Kharkar, P.; Reith, M. E.; Dutta, A. K. Development of (S)- N 6-(2-(4-(isoquinolin-1-yl)piperazin-1-yl)ethyl)- N 6-propyl-4,5,6,7-tetrahydrobenzo[ d ]-thiazole-2,6-diamine and its analogue as a D3 receptor preferring agonist: potent in vivo activity in Parkinson's disease animal models J. Med. Chem. 2010, 53, 1023-1037
    • (2010) J. Med. Chem. , vol.53 , pp. 1023-1037
    • Ghosh, B.1    Antonio, T.2    Zhen, J.3    Kharkar, P.4    Reith, M.E.5    Dutta, A.K.6
  • 34
    • 77955346226 scopus 로고    scopus 로고
    • Novel D3 dopamine receptor-preferring agonist D-264: Evidence of neuroprotective property in Parkinson's disease animal models induced by 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and lactacystin
    • Li, C.; Biswas, S.; Li, X.; Dutta, A. K.; Le, W. Novel D3 dopamine receptor-preferring agonist D-264: evidence of neuroprotective property in Parkinson's disease animal models induced by 1-methyl-4-phenyl-1,2,3,6- tetrahydropyridine and lactacystin J. Neurosci. Res. 2010, 88, 2513-2523
    • (2010) J. Neurosci. Res. , vol.88 , pp. 2513-2523
    • Li, C.1    Biswas, S.2    Li, X.3    Dutta, A.K.4    Le, W.5
  • 35
    • 79957597364 scopus 로고    scopus 로고
    • Dopamine D2/D3 agonists with potent iron chelation, antioxidant and neuroprotective properties: Potential implication in symptomatic and neuroprotective treatment of Parkinson's disease
    • Gogoi, S.; Antonio, T.; Rajagopalan, S.; Reith, M.; Andersen, J.; Dutta, A. K. Dopamine D2/D3 agonists with potent iron chelation, antioxidant and neuroprotective properties: potential implication in symptomatic and neuroprotective treatment of Parkinson's disease ChemMedChem 2011, 6, 991-995
    • (2011) ChemMedChem , vol.6 , pp. 991-995
    • Gogoi, S.1    Antonio, T.2    Rajagopalan, S.3    Reith, M.4    Andersen, J.5    Dutta, A.K.6
  • 36
    • 0030986012 scopus 로고    scopus 로고
    • Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations
    • Matuszak, Z.; Reszka, K.; Chignell, C. F. Reaction of melatonin and related indoles with hydroxyl radicals: EPR and spin trapping investigations Free Radical Biol. Med. 1997, 23, 367-372
    • (1997) Free Radical Biol. Med. , vol.23 , pp. 367-372
    • Matuszak, Z.1    Reszka, K.2    Chignell, C.F.3
  • 37
    • 0029974047 scopus 로고    scopus 로고
    • Molecular modeling parameters predict antioxidant efficacy of 3-indolyl compounds
    • Shertzer, H. G.; Tabor, M. W.; Hogan, I. T.; Brown, S. J.; Sainsbury, M. Molecular modeling parameters predict antioxidant efficacy of 3-indolyl compounds Arch. Toxicol. 1996, 70, 830-834
    • (1996) Arch. Toxicol. , vol.70 , pp. 830-834
    • Shertzer, H.G.1    Tabor, M.W.2    Hogan, I.T.3    Brown, S.J.4    Sainsbury, M.5
  • 40
    • 34247549751 scopus 로고    scopus 로고
    • Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit
    • Girennavar, B.; Jayaprakasha, G. K.; Jadegoud, Y.; Nagana Gowda, G. A.; Patil, B. S. Radical scavenging and cytochrome P450 3A4 inhibitory activity of bergaptol and geranylcoumarin from grapefruit Bioorg. Med. Chem. 2007, 15, 3684-3691
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 3684-3691
    • Girennavar, B.1    Jayaprakasha, G.K.2    Jadegoud, Y.3    Nagana Gowda, G.A.4    Patil, B.S.5
  • 41
    • 0000428532 scopus 로고
    • 3,4-Dihydroxyphenylalanine and 5-hydroxytryptophan as reserpine antagonists
    • Carlsson, A.; Lindqvist, M.; Magnusson, T. 3,4-Dihydroxyphenylalanine and 5-hydroxytryptophan as reserpine antagonists Nature 1957, 180, 1200
    • (1957) Nature , vol.180 , pp. 1200
    • Carlsson, A.1    Lindqvist, M.2    Magnusson, T.3
  • 42
    • 79957785934 scopus 로고    scopus 로고
    • N -(3-Fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl) arylcarboxamides as selective dopamine D3 receptor ligands: Critical role of the carboxamide linker for D3 receptor selectivity
    • Banala, A. K.; Levy, B. A.; Khatri, S. S.; Furman, C. A.; Roof, R. A.; Mishra, Y.; Griffin, S. A.; Sibley, D. R.; Luedtke, R. R.; Newman, A. H. N -(3-Fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl) arylcarboxamides as selective dopamine D3 receptor ligands: critical role of the carboxamide linker for D3 receptor selectivity J. Med. Chem. 2011, 54, 3581-3594
    • (2011) J. Med. Chem. , vol.54 , pp. 3581-3594
    • Banala, A.K.1    Levy, B.A.2    Khatri, S.S.3    Furman, C.A.4    Roof, R.A.5    Mishra, Y.6    Griffin, S.A.7    Sibley, D.R.8    Luedtke, R.R.9    Newman, A.H.10
  • 44
    • 23944521608 scopus 로고    scopus 로고
    • Sumanirole, a highly dopamine D2-selective receptor agonist: In vitro and in vivo pharmacological characterization and efficacy in animal models of Parkinson's disease
    • McCall, R. B.; Lookingland, K. J.; Bedard, P. J.; Huff, R. M. Sumanirole, a highly dopamine D2-selective receptor agonist: in vitro and in vivo pharmacological characterization and efficacy in animal models of Parkinson's disease J. Pharmacol. Exp. Ther. 2005, 314, 1248-1256
    • (2005) J. Pharmacol. Exp. Ther. , vol.314 , pp. 1248-1256
    • McCall, R.B.1    Lookingland, K.J.2    Bedard, P.J.3    Huff, R.M.4


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