메뉴 건너뛰기




Volumn 48, Issue 7, 2005, Pages 2678-2686

Discovery of the α7 nicotinic acetylcholine receptor agonists. (R)-3′-(5-chlorothiophen-2-yl)spiro-1-azabicyclo[2.2.2]octane-3, 5′-[1′,3′]-oxazolidin-2′-one as a novel, potent, selective, and orally bioavailable ligand

Author keywords

[No Author keywords available]

Indexed keywords

3' (5 CHLOROTHIOPHEN 2 YL)SPIRO 1 AZABICYCLO[2.2.2]OCTANE 3,5' [1',3']OXAZOLIDIN 2' ONE; BUNGAROTOXIN RECEPTOR; DIZOCILPINE; NICOTINIC AGENT; NICOTINIC RECEPTOR; OXAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG; 3' (5 CHLOROTHIOPHEN 2 YL)SPIRO 1 AZABICYCLO(2.2.2)OCTANE 3,5' (1',3') OXAZOLIDIN 2' ONE; 3'-(5-CHLOROTHIOPHEN-2-YL)SPIRO-1-AZABICYCLO(2.2.2)OCTANE-3,5'-(1',3')-OXAZOLIDIN-2'-ONE; ALPHA-BUNGAROTOXIN RECEPTOR; LIGAND; NEUROLEPTIC AGENT; OXAZOLE DERIVATIVE; QUINUCLIDINE DERIVATIVE;

EID: 17144370948     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049188d     Document Type: Article
Times cited : (53)

References (39)
  • 1
    • 0025856536 scopus 로고
    • Neuronal nicotinic acetylcholine receptors expressed in xenopus oocytes have a pentameric quaternary structure
    • Anand, R.; Conroy, W. G.; Schoepfer, R.; Whiting, P.; Lindstrom, J. Neuronal Nicotinic Acetylcholine Receptors Expressed in Xenopus Oocytes Have a Pentameric Quaternary Structure. J. Biol. Chem. 1991, 266 (11), 11192-11198.
    • (1991) J. Biol. Chem. , vol.266 , Issue.11 , pp. 11192-11198
    • Anand, R.1    Conroy, W.G.2    Schoepfer, R.3    Whiting, P.4    Lindstrom, J.5
  • 2
    • 0025828670 scopus 로고
    • Pentameric structure and subunit stoichiometry of a neuronal acetylcholine receptor
    • Cooper, E.; Couturier, S.; Ballivet, M. Pentameric Structure and Subunit Stoichiometry of a Neuronal Acetylcholine Receptor. Nature 1991, 350, 235-238.
    • (1991) Nature , vol.350 , pp. 235-238
    • Cooper, E.1    Couturier, S.2    Ballivet, M.3
  • 3
    • 0028965629 scopus 로고
    • Physiological diversity of nicotinic acetylcholine receptors expressed by vertebrate neurons
    • Mcgehee, D. S.; Role, L. W. Physiological Diversity of Nicotinic Acetylcholine Receptors Expressed by Vertebrate Neurons. Annu. Rev. Physiol. 1995, 57, 521-546.
    • (1995) Annu. Rev. Physiol. , vol.57 , pp. 521-546
    • Mcgehee, D.S.1    Role, L.W.2
  • 4
    • 0030175612 scopus 로고    scopus 로고
    • Nicotinic receptors in the development and modulation of CNS synapses
    • Role, L. W.; Berg, D. K. Nicotinic Receptors in the Development and Modulation of CNS Synapses. Neuron 1996,16, 1077-1085.
    • (1996) Neuron , vol.16 , pp. 1077-1085
    • Role, L.W.1    Berg, D.K.2
  • 5
    • 0027398069 scopus 로고
    • The diversity of neuronal nicotinic acetylcholine receptors
    • Sargent, P. The Diversity of Neuronal Nicotinic Acetylcholine Receptors. Annu. Rev. Neurosci. 1993, 16, 403-443.
    • (1993) Annu. Rev. Neurosci. , vol.16 , pp. 403-443
    • Sargent, P.1
  • 6
    • 0031032949 scopus 로고    scopus 로고
    • Presynaptic nicotinic ACh receptors
    • Wonnacott, S. Presynaptic Nicotinic ACh Receptors. Trends Neurosci. 1997, 20, 92-98.
    • (1997) Trends Neurosci. , vol.20 , pp. 92-98
    • Wonnacott, S.1
  • 7
    • 0026754804 scopus 로고
    • The alpha 5 gene product assembles with multiple acetylcholine receptor subunits to form distinctive receptor subtypes in brain
    • Conroy, W. G.; Vernallis, A. B.; Berg, D. K. The alpha 5 Gene Product Assembles with Multiple Acetylcholine Receptor Subunits to Form Distinctive Receptor Subtypes in Brain. Neuron 1992, 9, 679-691.
    • (1992) Neuron , vol.9 , pp. 679-691
    • Conroy, W.G.1    Vernallis, A.B.2    Berg, D.K.3
  • 8
    • 0031039785 scopus 로고    scopus 로고
    • Formation of oligomers containing the Beta3 and Beta4 subunits of the rat nicotinic receptor
    • Forsayeth, J. R.; Kobrin, E. Formation of Oligomers Containing the Beta3 and Beta4 Subunits of the Rat Nicotinic Receptor. J. Neurosci. 1997, 17, 1531-1538.
    • (1997) J. Neurosci. , vol.17 , pp. 1531-1538
    • Forsayeth, J.R.1    Kobrin, E.2
  • 9
    • 0029908722 scopus 로고    scopus 로고
    • Neuronal nicotonic alpha 6 subunit mRNA is selectively concentrated in catecholaminergic nuclei of the rat brain
    • Le Novere, N.; Zoli, M.; Changeux, J. P. Neuronal Nicotonic Alpha 6 Subunit mRNA is Selectively Concentrated in Catecholaminergic Nuclei of the Rat Brain. Eur. J. Neurosci. 1996, 8, 2428-2439.
    • (1996) Eur. J. Neurosci. , vol.8 , pp. 2428-2439
    • Le Novere, N.1    Zoli, M.2    Changeux, J.P.3
  • 10
    • 0029670191 scopus 로고    scopus 로고
    • Functional contributions of α5 subunit to neuronal acetylcholine receptor channels
    • Ramirez-LaTorre, J.; Yu, C.; Qu, X.; Perin, F.; Karlin, A.; Role, L. Functional Contributions of α5 Subunit to Neuronal Acetylcholine Receptor Channels. Nature 1996, 380, 37-351.
    • (1996) Nature , vol.380 , pp. 37-351
    • Ramirez-LaTorre, J.1    Yu, C.2    Qu, X.3    Perin, F.4    Karlin, A.5    Role, L.6
  • 11
    • 0027214596 scopus 로고
    • Mutations at two distinct sites within the channel domain M2 alter calcium permeability of neuronal α7 nicotinic receptor
    • Bertrand, D.; Galzi, J, L.; Devillers-Thiely, A.; Bertrand, S.; Changeux, J. P. Mutations at Two Distinct Sites within the Channel Domain M2 Alter Calcium Permeability of Neuronal α7 Nicotinic Receptor. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6971-6975.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 6971-6975
    • Bertrand, D.1    Galzi, J.L.2    Devillers-Thiely, A.3    Bertrand, S.4    Changeux, J.P.5
  • 12
    • 0025605864 scopus 로고
    • A neuronal nicotinic acetylcholine receptor subunit (α7) is developmentally regulated and forms a homo-oligomeric channel blocked by α-BTX
    • Couturier, S.; Bertrand, D.; Matter, J. M.; Hernandez, M. C.; Bertrand, S.; Millar, N.; Valera, S.; Barkas, T.; Ballivet, M. A Neuronal Nicotinic Acetylcholine Receptor Subunit (α7) is Developmentally Regulated and Forms a Homo-Oligomeric Channel Blocked by α-BTX. Neuron 1990, 5, 847-856.
    • (1990) Neuron , vol.5 , pp. 847-856
    • Couturier, S.1    Bertrand, D.2    Matter, J.M.3    Hernandez, M.C.4    Bertrand, S.5    Millar, N.6    Valera, S.7    Barkas, T.8    Ballivet, M.9
  • 13
    • 0025308827 scopus 로고
    • Brain α-bungarotoxin binding protein cDNAs and mAbs reveal subtypes of this branch of the ligand-gated ion channel gene superfamily
    • Schoepfer, R.; Conroy, W.; Whiting, P.; Gore, M.; Lindstrom, J. Brain α-Bungarotoxin Binding Protein cDNAs and mAbs Reveal Subtypes of This Branch of the Ligand-gated Ion Channel Gene Superfamily. Neuron 1990, 5, 35-48.
    • (1990) Neuron , vol.5 , pp. 35-48
    • Schoepfer, R.1    Conroy, W.2    Whiting, P.3    Gore, M.4    Lindstrom, J.5
  • 14
    • 0027518923 scopus 로고
    • Molecular cloning, functional properties, and distribution of rat brain α7: A nicotinic cation channel highly permeable to calcium
    • Séguéla, P.; Wadiche, J.; Dineley-Miller, K.; Dani, J. A.; Patrick, J. W. Molecular Cloning, Functional Properties, and Distribution of Rat Brain α7: A Nicotinic Cation Channel Highly Permeable to Calcium. J. Neurosci. 1993, 13, 596-604.
    • (1993) J. Neurosci. , vol.13 , pp. 596-604
    • Séguéla, P.1    Wadiche, J.2    Dineley-Miller, K.3    Dani, J.A.4    Patrick, J.W.5
  • 15
    • 0030753358 scopus 로고    scopus 로고
    • Nicotinic and muscarinic cholinergic receptor binding in the human hippocampal formation during development and aging
    • Court, J. A.; Lloyd, S.; Johnson, M.; Griffith, M.; Birdsall, N. J.; Piggott, M. A. Nicotinic and Muscarinic Cholinergic Receptor Binding in the Human Hippocampal Formation during Development and Aging. Brain Res. Dev. Brain Res. 1997,101, 93-105.
    • (1997) Brain Res. Dev. Brain Res. , vol.101 , pp. 93-105
    • Court, J.A.1    Lloyd, S.2    Johnson, M.3    Griffith, M.4    Birdsall, N.J.5    Piggott, M.A.6
  • 18
    • 0034017540 scopus 로고    scopus 로고
    • Nicotinic receptors in the brain. Links between molecular biology and behavior
    • Picciotto, M. R.; Caldarone, B. J.; King, S. L.; Zachariou, V. Nicotinic Receptors in the Brain. Links Between Molecular Biology and Behavior. Neuropsychopharmacology 2000, 22, 451-465.
    • (2000) Neuropsychopharmacology , vol.22 , pp. 451-465
    • Picciotto, M.R.1    Caldarone, B.J.2    King, S.L.3    Zachariou, V.4
  • 19
    • 0035251680 scopus 로고    scopus 로고
    • Cognitive effects of nicotine
    • Rezvani, A. H.; Levin, E. D. Cognitive Effects of Nicotine. Biol. Psychiatry 2001, 49, 258-267.
    • (2001) Biol. Psychiatry , vol.49 , pp. 258-267
    • Rezvani, A.H.1    Levin, E.D.2
  • 20
    • 0034934938 scopus 로고    scopus 로고
    • Cholinergic systems and schizophrenia: Primary pathology or epiphenomena?
    • Hyde, T. M.; Crook, J. M. Cholinergic Systems and Schizophrenia: Primary Pathology or Epiphenomena? J. Chem. Neuroanat. 2001, 22, 53-63.
    • (2001) J. Chem. Neuroanat. , vol.22 , pp. 53-63
    • Hyde, T.M.1    Crook, J.M.2
  • 22
    • 0026664965 scopus 로고
    • Cholinergic gating of response to auditory stimuli in rat hippocampus
    • Luntz-Leybman, V.; Bickford, P. C.; Freedman, R. Cholinergic Gating of Response to Auditory Stimuli in Rat Hippocampus. Brain Res. 1992, 587, 130-136.
    • (1992) Brain Res. , vol.587 , pp. 130-136
    • Luntz-Leybman, V.1    Bickford, P.C.2    Freedman, R.3
  • 23
    • 0033519564 scopus 로고    scopus 로고
    • Decreased protein level of nicotinic receptor α7 subunit in the frontal cortex from schizophrenic brain
    • Guan, Z.; Zhang, X.; Blennow, K.; Nordberg, A. Decreased Protein Level of Nicotinic Receptor α7 Subunit in the Frontal Cortex from Schizophrenic Brain. Neuroreport 1999, 10, 1779-1782.
    • (1999) Neuroreport , vol.10 , pp. 1779-1782
    • Guan, Z.1    Zhang, X.2    Blennow, K.3    Nordberg, A.4
  • 25
    • 0032872325 scopus 로고    scopus 로고
    • Neuronal nicotinic receptors in dementia with lewy bodies and schizophrenia: Alpha-bungarotoxin and nicotine binding in the thalamus
    • Court, J.; Spurden, D.; Lloyd, S.; McKeith, I.; Ballard, C.; Cairns, N.; Kerwin, R.; Perry, R.; Perry, E. Neuronal Nicotinic Receptors in Dementia with Lewy Bodies and Schizophrenia: Alpha-Bungarotoxin and Nicotine Binding in the Thalamus. J. Neurochem. 1999, 73, 1590-1597.
    • (1999) J. Neurochem. , vol.73 , pp. 1590-1597
    • Court, J.1    Spurden, D.2    Lloyd, S.3    McKeith, I.4    Ballard, C.5    Cairns, N.6    Kerwin, R.7    Perry, R.8    Perry, E.9
  • 26
    • 0032421378 scopus 로고    scopus 로고
    • GTS-21, a nicotinic agonist, attenuates multiple infarctions and cognitive deficits caused by permanent occlusion of bilateral common carotid arteries in rats
    • Nanri, M.; Miyake, H.; Murakami, Y.; Matsumoto, K.; Watanabe, H. GTS-21, a Nicotinic Agonist, Attenuates Multiple Infarctions and Cognitive Deficits Caused by Permanent Occlusion of Bilateral Common Carotid Arteries in Rats. Jpn. J. Pharmacol. 1998, 78, 463-469.
    • (1998) Jpn. J. Pharmacol. , vol.78 , pp. 463-469
    • Nanri, M.1    Miyake, H.2    Murakami, Y.3    Matsumoto, K.4    Watanabe, H.5
  • 27
    • 0032254325 scopus 로고    scopus 로고
    • Analysis of 3-(4-Hydroxy, 2-methoxybenzylidene)anabaseine selectivity and activity at human and rat alpha-7 nicotinic receptors
    • Meyer, E. M.; Kuryatov, A.; Gerzanich, V.; Lindstrom, J.; Papke, R. L. Analysis of 3-(4-Hydroxy, 2-methoxybenzylidene)Anabaseine Selectivity and Activity at Human and Rat alpha-7 Nicotinic Receptors. J. Pharmacol. Exp. Ther. 1998, 287, 918-925.
    • (1998) J. Pharmacol. Exp. Ther. , vol.287 , pp. 918-925
    • Meyer, E.M.1    Kuryatov, A.2    Gerzanich, V.3    Lindstrom, J.4    Papke, R.L.5
  • 29
    • 2942620549 scopus 로고    scopus 로고
    • (+)-3-[2-(Benzo[b]thiophen-2-yl)-2-oxoethyl]-1-azabicyclo[2.2.2]octane as potent agonists for the α7 nicotinic acetylcholine receptor
    • Tatsumi, R.; Seio, K.; Fujio, M.; Katayama, J.; Horikawa, T.; Hashimoto, K.; Tanaka, H. (+)-3-[2-(Benzo[b]thiophen-2-yl)-2-oxoethyl]-1-azabicyclo[2.2.2] octane as Potent Agonists for the α7 Nicotinic Acetylcholine Receptor. Bioorg. Med. Chem. Lett. 2004, 14, 3781-3784.
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 3781-3784
    • Tatsumi, R.1    Seio, K.2    Fujio, M.3    Katayama, J.4    Horikawa, T.5    Hashimoto, K.6    Tanaka, H.7
  • 30
    • 0033626286 scopus 로고    scopus 로고
    • The brain α7 nicotinic receptor may be an important therapeutic target for the treatment of Alzheimer's disease: Studies with DMXBA (GTS-21)
    • Kem, W. R. The Brain α7 Nicotinic Receptor May Be an Important Therapeutic Target for the Treatment of Alzheimer's Disease: Studies with DMXBA (GTS-21). Behav. Brain Res. 2000, 113, 169-181.
    • (2000) Behav. Brain Res. , vol.113 , pp. 169-181
    • Kem, W.R.1
  • 31
    • 0031425178 scopus 로고    scopus 로고
    • Rats reared in social isolation show schizophrenia-like changes in auditory gating
    • Stevens, K. E.; Johnson, R. G.; Rose, G. M. Rats Reared in Social Isolation Show Schizophrenia-Like Changes in Auditory Gating. Pharmacol. Biochem. Behav. 1997, 58, 1031-1036.
    • (1997) Pharmacol. Biochem. Behav. , vol.58 , pp. 1031-1036
    • Stevens, K.E.1    Johnson, R.G.2    Rose, G.M.3
  • 32
    • 0026472046 scopus 로고
    • Normalization by nicotine of deficient auditory sensory gating in the relatives of schizophrenics
    • Adler, L. E.; Hoffer, L. J.; Griffith, J.; Waldo, M. C.; Freedman, R. Normalization by Nicotine of Deficient Auditory Sensory Gating in the Relatives of Schizophrenics. Biol. Psychiatry 1992, 32, 607-616.
    • (1992) Biol. Psychiatry , vol.32 , pp. 607-616
    • Adler, L.E.1    Hoffer, L.J.2    Griffith, J.3    Waldo, M.C.4    Freedman, R.5
  • 34
    • 0034062159 scopus 로고    scopus 로고
    • Normal P50 suppression in schizophrenia patients treated with atypical antipsychotic medications
    • Light, G. A.; Geyer, M. A.; Clementz, B. A.; Cadenhead, K. S.; Braff, D. L. Normal P50 Suppression in Schizophrenia Patients Treated with Atypical Antipsychotic Medications. Am. J. Psychiatry. 2000, 157, 767-771.
    • (2000) Am. J. Psychiatry , vol.157 , pp. 767-771
    • Light, G.A.1    Geyer, M.A.2    Clementz, B.A.3    Cadenhead, K.S.4    Braff, D.L.5
  • 36
    • 0030845922 scopus 로고    scopus 로고
    • The α-bungarotoxin-binding nicotinic acetylcholine receptor from rat brain contains only the α7 subunit
    • Chen, D.; Patrick, J. W. The α-Bungarotoxin-binding Nicotinic Acetylcholine Receptor from Rat Brain Contains Only the α7 Subunit. J. Biol. Chem. 1997, 272, 24024-24029.
    • (1997) J. Biol. Chem. , vol.272 , pp. 24024-24029
    • Chen, D.1    Patrick, J.W.2
  • 37
    • 17144402326 scopus 로고
    • Kinetics of the reactions of some 5-bromo-2-nitro-3-R-thiophenes, 3,4-dibromo-2-nitro-5-R-thiophens, 3-bromo-2-nitro-5-R-thiophenes, and 2-bromo-3-nitro-5-R-thiophenes with nucleophiles in methanol
    • Giovanni, C.; Domenico, S.; Salo, G.; Anna-Britta, H.; Britta, M.; Renato, N. Kinetics of the Reactions of Some 5-Bromo-2-nitro-3-R-thiophenes, 3,4-dibromo-2-nitro-5-R-thiophens, 3-bromo-2-nitro-5-R-thiophenes, and 2-bromo-3-nitro-5-R-thiophenes with Nucleophiles in Methanol. J. Chem. Soc. Perkin Trans. 2 1982, 5, 625-630.
    • (1982) J. Chem. Soc. Perkin Trans. 2 , vol.5 , pp. 625-630
    • Giovanni, C.1    Domenico, S.2    Salo, G.3    Anna-Britta, H.4    Britta, M.5    Renato, N.6
  • 39
    • 0027226219 scopus 로고
    • Optimized survival of hippocampal neurons in B-27-supplemented neurobasal, a new serum-free medium combination
    • Brewer, G. J.; Torricelli, J. R.; Evege, E. K.; Price, P. J. Optimized Survival of Hippocampal Neurons in B-27-Supplemented Neurobasal, a New Serum-Free Medium Combination. J. Neurosci. Res. 1993, 35, 567-576.
    • (1993) J. Neurosci. Res. , vol.35 , pp. 567-576
    • Brewer, G.J.1    Torricelli, J.R.2    Evege, E.K.3    Price, P.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.