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Volumn 53, Issue 19, 2010, Pages 6973-6985

Chemistry and pharmacological characterization of novel nitrogen analogues of AMOP-H-OH (sazetidine-A, 6-[5-(azetidin-2-ylmethoxy)pyridin-3-yl]hex-5-yn-1- ol) as α4β2-nicotinic acetylcholine receptor-selective partial agonists

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 INDOLINYL) 5 [(2 PYRROLIDINYL)METHOXY]PYRIDINE; 3 (1 INDOLYL) 5 (2 PYRROLIDINYLMETHOXY)PYRIDINE; 3 (1,3 DIHYDROISOINDOL 2 YL) 5 [(2 PYRROLIDINYL)METHOXY]PYRIDINE; 3 [(1 METHYL 2 AZETIDINYL)METHOXY] 5 (PIPERIDINYL)PYRIDINE; 3 [(1 METHYL 2 PYRROLIDINYL)METHOXY] 5 (PIPERIDINYL)PYRIDINE; 3 [(2 AZETIDINYL)METHOXY] 5 (PIPERIDINYL)PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 (MORPHOLINYL)PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 (PIPERAZINYL)PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 (PIPERIDINYL)PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 (PYRROLIDINYL)PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 BENZYLAMINOPYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 BUTYLAMINOPYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 DIETHYLAMINOPYRIDIN; 3 [(2 PYRROLIDINYL)METHOXY] 5 PHENYLAMINOPYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 [(N ETHYL N PHENYL)AMINO]PYRIDINE; 3 [(2 PYRROLIDINYL)METHOXY] 5 [(N METHYL N BENZYL)AMINO]PYRIDINE; ANTIDEPRESSANT AGENT; NICOTINIC AGENT; NICOTINIC RECEPTOR; NICOTINIC RECEPTOR ALPHA3BETA4; NICOTINIC RECEPTOR ALPHA4BETA2; NITROGEN DERIVATIVE; PYRIDINE DERIVATIVE; SAZETIDINE A; UNCLASSIFIED DRUG; 3-((2-PYRROLIDINYL)METHOXY)-5-PHENYLAMINOPYRIDINE; AMINOPYRIDINE DERIVATIVE; AZETIDINE DERIVATIVE; LIGAND; PYRROLIDINE DERIVATIVE; SAZETIDINE-A;

EID: 77957898423     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100765u     Document Type: Article
Times cited : (21)

References (53)
  • 4
    • 0032934644 scopus 로고    scopus 로고
    • Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine
    • Fryer, J. D.; Lukas, R. J. Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine J. Pharmacol. Exp. Ther. 1999, 288, 88-92
    • (1999) J. Pharmacol. Exp. Ther. , vol.288 , pp. 88-92
    • Fryer, J.D.1    Lukas, R.J.2
  • 5
    • 0033014178 scopus 로고    scopus 로고
    • Antidepressants noncompetitively inhibit nicotinic acetylcholine receptor function
    • Fryer, J. D.; Lukas, R. J. Antidepressants noncompetitively inhibit nicotinic acetylcholine receptor function J. Neurochem. 1999, 72, 1117-1124
    • (1999) J. Neurochem. , vol.72 , pp. 1117-1124
    • Fryer, J.D.1    Lukas, R.J.2
  • 6
    • 4944267468 scopus 로고    scopus 로고
    • Enantioselective effects of hydroxy metabolites of bupropion on behavior and on function of monoamine transporters and nicotinic receptors
    • Damaj, M. I.; Carroll, F. I.; Eaton, J. B.; Navarro, H. A.; Blough, B. E.; Mirza, S.; Lukas, R. J.; Martin, B. R. Enantioselective effects of hydroxy metabolites of bupropion on behavior and on function of monoamine transporters and nicotinic receptors Mol. Pharmacol. 2004, 66, 675-682
    • (2004) Mol. Pharmacol. , vol.66 , pp. 675-682
    • Damaj, M.I.1    Carroll, F.I.2    Eaton, J.B.3    Navarro, H.A.4    Blough, B.E.5    Mirza, S.6    Lukas, R.J.7    Martin, B.R.8
  • 8
    • 77949348035 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for smoking cessation
    • Carroll, F. I.; Blough, B. E.; Mascarella, S. W.; Navarro, H. A.; Eaton, J. B.; Lukas, R. J.; Damaj, M. I. Synthesis and biological evaluation of bupropion analogues as potential pharmacotherapies for smoking cessation J. Med. Chem. 2010, 53, 2204-2214
    • (2010) J. Med. Chem. , vol.53 , pp. 2204-2214
    • Carroll, F.I.1    Blough, B.E.2    Mascarella, S.W.3    Navarro, H.A.4    Eaton, J.B.5    Lukas, R.J.6    Damaj, M.I.7
  • 9
    • 63849213473 scopus 로고    scopus 로고
    • Nicotinic acetylcholine receptor signalling: Roles in Alzheimer's disease and amyloid neuroprotection
    • Buckingham, S. D.; Jones, A. K.; Brown, L. A.; Sattelle, D. B. Nicotinic acetylcholine receptor signalling: roles in Alzheimer's disease and amyloid neuroprotection Pharmacol. Rev. 2009, 61, 39-61
    • (2009) Pharmacol. Rev. , vol.61 , pp. 39-61
    • Buckingham, S.D.1    Jones, A.K.2    Brown, L.A.3    Sattelle, D.B.4
  • 10
    • 34548674712 scopus 로고    scopus 로고
    • Nicotinic receptors as CNS targets for Parkinson's disease
    • Quik, M.; Bordia, T.; O'Leary, K. Nicotinic receptors as CNS targets for Parkinson's disease Biochem. Pharmacol. 2007, 74, 1224-1234
    • (2007) Biochem. Pharmacol. , vol.74 , pp. 1224-1234
    • Quik, M.1    Bordia, T.2    O'leary, K.3
  • 11
    • 34548670751 scopus 로고    scopus 로고
    • Neuronal nicotinic receptor agonists for the treatment of attention-deficit/hyperactivity disorder: Focus on cognition
    • Wilens, T. E.; Decker, M. W. Neuronal nicotinic receptor agonists for the treatment of attention-deficit/hyperactivity disorder: focus on cognition Biochem. Pharmacol. 2007, 74, 1212-1223
    • (2007) Biochem. Pharmacol. , vol.74 , pp. 1212-1223
    • Wilens, T.E.1    Decker, M.W.2
  • 12
    • 33744512777 scopus 로고    scopus 로고
    • Functional brain imaging of tobacco use and dependence
    • Brody, A. L. Functional brain imaging of tobacco use and dependence J. Psychiatr. Res. 2006, 40, 404-418
    • (2006) J. Psychiatr. Res. , vol.40 , pp. 404-418
    • Brody, A.L.1
  • 13
    • 52949104082 scopus 로고    scopus 로고
    • The role of alpha7 and alpha4beta2 nicotinic receptors in the nicotine-induced anxiolytic effect in zebrafish
    • Bencan, Z.; Levin, E. D. The role of alpha7 and alpha4beta2 nicotinic receptors in the nicotine-induced anxiolytic effect in zebrafish Physiol. Behav. 2008, 95, 408-412
    • (2008) Physiol. Behav. , vol.95 , pp. 408-412
    • Bencan, Z.1    Levin, E.D.2
  • 14
    • 0032807022 scopus 로고    scopus 로고
    • Therapeutic potential of neuronal nicotinic acetylcholine receptor agonists as novel analgesics
    • Decker, M. W.; Meyer, M. D. Therapeutic potential of neuronal nicotinic acetylcholine receptor agonists as novel analgesics Biochem. Pharmacol. 1999, 58, 917-923
    • (1999) Biochem. Pharmacol. , vol.58 , pp. 917-923
    • Decker, M.W.1    Meyer, M.D.2
  • 15
    • 33847351996 scopus 로고    scopus 로고
    • Schizophrenia and the alpha7 nicotinic acetylcholine receptor
    • Martin, L. F.; Freedman, R. Schizophrenia and the alpha7 nicotinic acetylcholine receptor Int. Rev. Neurobiol. 2007, 78, 225-246
    • (2007) Int. Rev. Neurobiol. , vol.78 , pp. 225-246
    • Martin, L.F.1    Freedman, R.2
  • 16
    • 34447134086 scopus 로고    scopus 로고
    • Cognitive deficits in schizophrenia: Focus on neuronal nicotinic acetylcholine receptors and smoking
    • Ochoa, E. L.; Lasalde-Dominicci, J. Cognitive deficits in schizophrenia: focus on neuronal nicotinic acetylcholine receptors and smoking Cell Mol. Neurobiol. 2007, 27, 609-639
    • (2007) Cell Mol. Neurobiol. , vol.27 , pp. 609-639
    • Ochoa, E.L.1    Lasalde-Dominicci, J.2
  • 17
    • 39749147634 scopus 로고    scopus 로고
    • Nicotinic acetylcholine receptors in cancer: Multiple roles in proliferation and inhibition of apoptosis
    • Egleton, R. D.; Brown, K. C.; Dasgupta, P. Nicotinic acetylcholine receptors in cancer: multiple roles in proliferation and inhibition of apoptosis Trends Pharmacol. Sci. 2008, 29, 151-158
    • (2008) Trends Pharmacol. Sci. , vol.29 , pp. 151-158
    • Egleton, R.D.1    Brown, K.C.2    Dasgupta, P.3
  • 18
    • 22844432580 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors: Structural revelations, target identifications, and therapeutic inspirations
    • Jensen, A. A.; Frolund, B.; Liljefors, T.; Krogsgaard-Larsen, P. Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations J. Med. Chem. 2005, 48, 4705-4745
    • (2005) J. Med. Chem. , vol.48 , pp. 4705-4745
    • Jensen, A.A.1    Frolund, B.2    Liljefors, T.3    Krogsgaard-Larsen, P.4
  • 19
    • 0030941561 scopus 로고    scopus 로고
    • Pharmacological characterization of recombinant human neuronal nicotinic acetylcholine receptors h alpha 2 beta 2, h alpha 2 beta 4, h alpha 3 beta 2, h alpha 3 beta 4, h alpha 4 beta 2, h alpha 4 beta 4 and h alpha 7 expressed in Xenopus oocytes
    • Chavez-Noriega, L. E.; Crona, J. H.; Washburn, M. S.; Urrutia, A.; Elliott, K. J.; Johnson, E. C. Pharmacological characterization of recombinant human neuronal nicotinic acetylcholine receptors h alpha 2 beta 2, h alpha 2 beta 4, h alpha 3 beta 2, h alpha 3 beta 4, h alpha 4 beta 2, h alpha 4 beta 4 and h alpha 7 expressed in Xenopus oocytes J. Pharmacol. Exp. Ther. 1997, 280, 346-356
    • (1997) J. Pharmacol. Exp. Ther. , vol.280 , pp. 346-356
    • Chavez-Noriega, L.E.1    Crona, J.H.2    Washburn, M.S.3    Urrutia, A.4    Elliott, K.J.5    Johnson, E.C.6
  • 20
    • 54049101939 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors: From the genetic analysis to neurological diseases
    • Steinlein, O. K.; Bertrand, D. Neuronal nicotinic acetylcholine receptors: from the genetic analysis to neurological diseases Biochem. Pharmacol. 2008, 76, 1175-1183
    • (2008) Biochem. Pharmacol. , vol.76 , pp. 1175-1183
    • Steinlein, O.K.1    Bertrand, D.2
  • 22
    • 16244411975 scopus 로고    scopus 로고
    • 6′-Methylpyrido[3,4- b ]norhomotropane: Synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model
    • Kanne, D. B.; Tomizawa, M.; Durkin, K. A.; Casida, J. E. 6′-Methylpyrido[3,4- b ]norhomotropane: synthesis and outstanding potency in relation to the alpha4beta2 nicotinic receptor pharmacophore model Bioorg. Med. Chem. Lett. 2005, 15, 877-881
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 877-881
    • Kanne, D.B.1    Tomizawa, M.2    Durkin, K.A.3    Casida, J.E.4
  • 26
    • 67650729927 scopus 로고    scopus 로고
    • Octahydropyrrolo[3,4- c ]pyrrole: A diamine scaffold for construction of either alpha4beta2 or alpha7-selective nicotinic acetylcholine receptor (nAChR) ligands. Substitutions that switch subtype selectivity
    • Bunnelle, W. H.; Tietje, K. R.; Frost, J. M.; Peters, D.; Ji, J.; Li, T.; Scanio, M. J.; Shi, L.; Anderson, D. J.; Dyhring, T.; Gronlien, J. H.; Ween, H.; Thorin-Hagene, K.; Meyer, M. D. Octahydropyrrolo[3,4- c ]pyrrole: a diamine scaffold for construction of either alpha4beta2 or alpha7-selective nicotinic acetylcholine receptor (nAChR) ligands. Substitutions that switch subtype selectivity J. Med. Chem. 2009, 52, 4126-4141
    • (2009) J. Med. Chem. , vol.52 , pp. 4126-4141
    • Bunnelle, W.H.1    Tietje, K.R.2    Frost, J.M.3    Peters, D.4    Ji, J.5    Li, T.6    Scanio, M.J.7    Shi, L.8    Anderson, D.J.9    Dyhring, T.10    Gronlien, J.H.11    Ween, H.12    Thorin-Hagene, K.13    Meyer, M.D.14
  • 27
    • 0033960085 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as novel drug targets
    • Lloyd, G. K.; Williams, M. Neuronal nicotinic acetylcholine receptors as novel drug targets J. Pharmacol. Exp. Ther. 2000, 292, 461-467
    • (2000) J. Pharmacol. Exp. Ther. , vol.292 , pp. 461-467
    • Lloyd, G.K.1    Williams, M.2
  • 31
    • 33747761302 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as a target for the treatment of neuropathic pain
    • Meyer, M. D. Neuronal nicotinic acetylcholine receptors as a target for the treatment of neuropathic pain Drug Dev. Res. 2006, 67, 355-359
    • (2006) Drug Dev. Res. , vol.67 , pp. 355-359
    • Meyer, M.D.1
  • 34
    • 33748927988 scopus 로고    scopus 로고
    • Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them
    • Xiao, Y.; Fan, H.; Musachio, J. L.; Wei, Z. L.; Chellappan, S. K.; Kozikowski, A. P.; Kellar, K. J. Sazetidine-A, a novel ligand that desensitizes alpha4beta2 nicotinic acetylcholine receptors without activating them Mol. Pharmacol. 2006, 70, 1454-1460
    • (2006) Mol. Pharmacol. , vol.70 , pp. 1454-1460
    • Xiao, Y.1    Fan, H.2    Musachio, J.L.3    Wei, Z.L.4    Chellappan, S.K.5    Kozikowski, A.P.6    Kellar, K.J.7
  • 36
  • 38
    • 15444377115 scopus 로고    scopus 로고
    • Novel pyridyl ring C5 substituted analogues of epibatidine and 3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine (A-84543) as highly selective agents for neuronal nicotinic acetylcholine receptors containing beta2 subunits
    • Wei, Z. L.; Xiao, Y.; Yuan, H.; Baydyuk, M.; Petukhov, P. A.; Musachio, J. L.; Kellar, K. J.; Kozikowski, A. P. Novel pyridyl ring C5 substituted analogues of epibatidine and 3-(1-methyl-2(S)-pyrrolidinylmethoxy)pyridine (A-84543) as highly selective agents for neuronal nicotinic acetylcholine receptors containing beta2 subunits J. Med. Chem. 2005, 48, 1721-1724
    • (2005) J. Med. Chem. , vol.48 , pp. 1721-1724
    • Wei, Z.L.1    Xiao, Y.2    Yuan, H.3    Baydyuk, M.4    Petukhov, P.A.5    Musachio, J.L.6    Kellar, K.J.7    Kozikowski, A.P.8
  • 39
    • 0018937071 scopus 로고
    • Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates
    • Ortiz de Montellano, P. R.; Kunze, K. L. Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates J. Biol. Chem. 1980, 255, 5578-5585
    • (1980) J. Biol. Chem. , vol.255 , pp. 5578-5585
    • Ortiz De Montellano, P.R.1    Kunze, K.L.2
  • 42
    • 0017651126 scopus 로고
    • Behavioral despair in mice: A primary screening test for antidepressants
    • Porsolt, R. D.; Bertin, A.; Jalfre, M. Behavioral despair in mice: a primary screening test for antidepressants Arch. Int. Pharmacodyn. Ther. 1977, 229, 327-336
    • (1977) Arch. Int. Pharmacodyn. Ther. , vol.229 , pp. 327-336
    • Porsolt, R.D.1    Bertin, A.2    Jalfre, M.3
  • 43
    • 0001038733 scopus 로고    scopus 로고
    • Rational development of practical catalysts for aromatic carbon-nitrogen bond formation
    • Wolfe, J. P.; Wagaw, S.; Marcoux, J. F.; Buchwald, S. L. Rational development of practical catalysts for aromatic carbon-nitrogen bond formation Acc. Chem. Res. 1998, 31, 805-818
    • (1998) Acc. Chem. Res. , vol.31 , pp. 805-818
    • Wolfe, J.P.1    Wagaw, S.2    Marcoux, J.F.3    Buchwald, S.L.4
  • 44
    • 52049105452 scopus 로고    scopus 로고
    • Biaryl phosphane ligands in palladium-catalyzed amination
    • Surry, D. S.; Buchwald, S. L. Biaryl phosphane ligands in palladium-catalyzed amination Angew. Chem., Int. Ed. Engl. 2008, 47, 6338-6361
    • (2008) Angew. Chem., Int. Ed. Engl. , vol.47 , pp. 6338-6361
    • Surry, D.S.1    Buchwald, S.L.2
  • 45
    • 33644758151 scopus 로고    scopus 로고
    • Methods to assess drug permeability across the blood-brain barrier
    • Nicolazzo, J. A.; Charman, S. A.; Charman, W. N. Methods to assess drug permeability across the blood-brain barrier J. Pharm. Pharmacol. 2006, 58, 281-293
    • (2006) J. Pharm. Pharmacol. , vol.58 , pp. 281-293
    • Nicolazzo, J.A.1    Charman, S.A.2    Charman, W.N.3
  • 46
    • 77954058432 scopus 로고    scopus 로고
    • Insights for predicting blood-brain barrier penetration of CNS targeted molecules using QSPR approaches
    • Fan, Y.; Unwalla, R.; Denny, R. A.; Di, L.; Kerns, E. H.; Diller, D. J.; Humblet, C. Insights for predicting blood-brain barrier penetration of CNS targeted molecules using QSPR approaches J. Chem. Inf. Model. 2010, 50, 1123-1133
    • (2010) J. Chem. Inf. Model. , vol.50 , pp. 1123-1133
    • Fan, Y.1    Unwalla, R.2    Denny, R.A.3    Di, L.4    Kerns, E.H.5    Diller, D.J.6    Humblet, C.7
  • 47
    • 33644860349 scopus 로고    scopus 로고
    • The impact of microwave-assisted organic synthesis in drug discovery
    • Mavandadi, F.; Pilotti, A. The impact of microwave-assisted organic synthesis in drug discovery Drug Discovery Today 2006, 11, 165-174
    • (2006) Drug Discovery Today , vol.11 , pp. 165-174
    • Mavandadi, F.1    Pilotti, A.2
  • 48
    • 0023198434 scopus 로고
    • Is agonist self-inhibition at the nicotinic acetylcholine receptor a nonspecific action?
    • Forman, S. A.; Firestone, L. L.; Miller, K. W. Is agonist self-inhibition at the nicotinic acetylcholine receptor a nonspecific action? Biochemistry 1987, 26, 2807-2814
    • (1987) Biochemistry , vol.26 , pp. 2807-2814
    • Forman, S.A.1    Firestone, L.L.2    Miller, K.W.3
  • 49
    • 0029863212 scopus 로고    scopus 로고
    • Agonist self-inhibitory binding site of the nicotinic acetylcholine receptor
    • Arias, H. R. Agonist self-inhibitory binding site of the nicotinic acetylcholine receptor J. Neurosci. Res. 1996, 44, 97-105
    • (1996) J. Neurosci. Res. , vol.44 , pp. 97-105
    • Arias, H.R.1
  • 52
    • 0027468584 scopus 로고
    • Characterization of Nicotinic Acetylcholine Receptors Expressed by Cells of the SH-SY5Y Human Neuroblastoma Clonal Line
    • Lukas, R. J.; Norman, S. A.; Lucero, L. Characterization of Nicotinic Acetylcholine Receptors Expressed by Cells of the SH-SY5Y Human Neuroblastoma Clonal Line Mol. Cell Neurosci. 1993, 4, 1-12
    • (1993) Mol. Cell Neurosci. , vol.4 , pp. 1-12
    • Lukas, R.J.1    Norman, S.A.2    Lucero, L.3
  • 53
    • 10744221698 scopus 로고    scopus 로고
    • Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells
    • Eaton, J. B.; Peng, J. H.; Schroeder, K. M.; George, A. A.; Fryer, J. D.; Krishnan, C.; Buhlman, L.; Kuo, Y. P.; Steinlein, O.; Lukas, R. J. Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells Mol. Pharmacol. 2003, 64, 1283-1294
    • (2003) Mol. Pharmacol. , vol.64 , pp. 1283-1294
    • Eaton, J.B.1    Peng, J.H.2    Schroeder, K.M.3    George, A.A.4    Fryer, J.D.5    Krishnan, C.6    Buhlman, L.7    Kuo, Y.P.8    Steinlein, O.9    Lukas, R.J.10


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