메뉴 건너뛰기




Volumn 46, Issue 11, 2003, Pages 2031-2048

3D QSAR analyses-guided rational design of novel ligands for the (α4)2(β2)3 nicotinic acetylcholine receptor

Author keywords

[No Author keywords available]

Indexed keywords

2 (2' CHLOROPYRIMIDIN 5' YL) 8 AZABICYCLO[3.2.1]OCT 2 ENE; 2 (3' CHLOROPYRAZIN 2' YL) 8 AZABICYCLO[3.2.1]OCT 2 ENE; 2 (3' PYRIDINYL) 8 AZABICYCLO[3.2.1]OCT 2 ENE; 3 (2' CHLOROPYRIMIDIN 5' YL) 8 AZABICYCLO[3.2.1]OCT 2 ENE; 3 (3' CHLOROPYRAZIN 2' YL) 8 AZABICYCLO[3.2.1]OCT 2 ENE; 3 (3' PYRIDINYL) 8 AZABICYCLO[3.2.1]OCT 2 ENE MALEATE; 8 AZABICYCLO[3.2.1]OCT 2 ENE CARBOXYLIC ACID DIMETHYLAMIDE; 8 AZABICYCLO[3.2.1]OCT 2 ENE THIOCARBOXYLIC ACID DIMETHYLAMIDE; 8 METHYL 8 AZABICYCLO[3.2.1]OCT 2 ENE 2 CARBOXYLIC ACID DIMETHYLAMIDE; 8 METHYL 8 AZABICYCLO[3.2.1]OCT 2 ENE 2 THIOCARBOXYLIC ACID DIMETHYLAMIDE; ANATOXIN A; CYTISINE; EPIBATIDINE; NICOTINIC AGENT; NICOTINIC RECEPTOR; UNCLASSIFIED DRUG;

EID: 0037573351     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020859m     Document Type: Article
Times cited : (50)

References (77)
  • 1
    • 0031450275 scopus 로고    scopus 로고
    • Neuronal nicotinic acetylcholine receptors as targets for drug discovery
    • Holladay, M. W.; Dart, M. J.; Lynch, J. K. Neuronal Nicotinic Acetylcholine Receptors as Targets for Drug Discovery. J. Med. Chem. 1997, 40, 4169-4194.
    • (1997) J. Med. Chem. , vol.40 , pp. 4169-4194
    • Holladay, M.W.1    Dart, M.J.2    Lynch, J.K.3
  • 2
    • 0031904673 scopus 로고    scopus 로고
    • Recent developments in neuronal nicotinic acetylcholine receptor modulators
    • Lin, N.-H.; Meyer, M. D. Recent Developments in Neuronal Nicotinic Acetylcholine Receptor Modulators. Exp. Opin. Ther. Patents 1998, 8, 991-1015.
    • (1998) Exp. Opin. Ther. Patents , vol.8 , pp. 991-1015
    • Lin, N.-H.1    Meyer, M.D.2
  • 3
    • 0033927801 scopus 로고    scopus 로고
    • Exploring the nature of molecular recognition in nicotinic acetylcholine receptors
    • Schmitt, J. D. Exploring the Nature of Molecular Recognition in Nicotinic Acetylcholine Receptors. Curr. Med. Chem. 2000, 7, 749-800.
    • (2000) Curr. Med. Chem. , vol.7 , pp. 749-800
    • Schmitt, J.D.1
  • 4
    • 0034744270 scopus 로고    scopus 로고
    • Agonists at the α4β2 nicotinic acetylcholine receptors: Structure-activity relationships and molecular modelling
    • Tonder, J. E.; Olesen, P. H. Agonists at the α4β2 Nicotinic Acetylcholine Receptors: Structure-Activity Relationships and Molecular Modelling. Curr. Med. Chem. 2001, 8, 651-674.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 651-674
    • Tonder, J.E.1    Olesen, P.H.2
  • 5
    • 0026551490 scopus 로고
    • Epibatidine: A novel (Chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog
    • Spande, T. F.; Garaffo, H. M.; Edward, M. W.; Yeh, H. J. C.; Pannell, L.; Daly, J. W. Epibatidine: A Novel (Chloropyridyl)azabicycloheptane with Potent Analgesic Activity from an Ecuadoran Poison Frog. J. Am. Chem. Soc. 1992, 114, 3475-3478.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 3475-3478
    • Spande, T.F.1    Garaffo, H.M.2    Edward, M.W.3    Yeh, H.J.C.4    Pannell, L.5    Daly, J.W.6
  • 6
    • 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
  • 8
    • 0030670102 scopus 로고    scopus 로고
    • Synthesis of UB-165: A novel nicotinic ligand and anatoxina/epibatidine hybrid
    • Wrigth, E.; Gallagher, T.; Sharples, C. G. V.; Wonnacott, S. Synthesis of UB-165: A Novel Nicotinic Ligand and Anatoxina/Epibatidine Hybrid. Bioorg. Med. Chem. Lett. 1997, 7, 2867-2870.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2867-2870
    • Wrigth, E.1    Gallagher, T.2    Sharples, C.G.V.3    Wonnacott, S.4
  • 9
    • 0034732362 scopus 로고    scopus 로고
    • The identification of novel structural compound classes exhibiting high affinity for neuronal nicotinic acetylcholine receptors and analgesic efficacy in preclinical models of pain
    • Meyer, D. M.; Decker, M. W.; Rueter, L. E.; Anderson, D. J.; Dart, M. J.; Kim, K. H.; Sullivan, J. P.; Williams, M. The Identification of Novel Structural Compound Classes Exhibiting High Affinity for Neuronal Nicotinic Acetylcholine Receptors and Analgesic Efficacy in Preclinical Models of Pain. Eur. J. Pharmacol. 2000, 393, 171-177.
    • (2000) Eur. J. Pharmacol. , vol.393 , pp. 171-177
    • Meyer, D.M.1    Decker, M.W.2    Rueter, L.E.3    Anderson, D.J.4    Dart, M.J.5    Kim, K.H.6    Sullivan, J.P.7    Williams, M.8
  • 10
    • 0030759242 scopus 로고    scopus 로고
    • Synthesis and nicotinic acetylcholine receptor binding properties of exo-2-(2′Fluoro-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane: A new positron emission tomography ligand for nicotinic receptors
    • Liang, F.; Navarro, H. A.; Abraham, P.; Kotian, P.; Ding, Y.-S.; Fowler, J.; Volkow, N.; Kuhar, M. J.; Carrol, F. I. Synthesis and Nicotinic Acetylcholine Receptor Binding Properties of exo-2-(2′Fluoro-5′-pyridinyl)-7-azabicyclo[2.2.1]heptane: A New Positron Emission Tomography Ligand for Nicotinic Receptors. J. Med. Chem. 1997, 40, 2293-2295.
    • (1997) J. Med. Chem. , vol.40 , pp. 2293-2295
    • Liang, F.1    Navarro, H.A.2    Abraham, P.3    Kotian, P.4    Ding, Y.-S.5    Fowler, J.6    Volkow, N.7    Kuhar, M.J.8    Carrol, F.I.9
  • 11
    • 0037130235 scopus 로고    scopus 로고
    • Synthesis and pharmacological characterization of novel analogues of the nicotinic acetylcholine receptor agonist (±)-UB-165
    • Sharpless, C. G. V.; Karig, G.; Simpson, G. L.; Spencer, J. A.; Wright, E.; Milar, N. S.; Wonnacott, S.; Gallagher, T. Synthesis and Pharmacological Characterization of Novel Analogues of the Nicotinic Acetylcholine Receptor Agonist (±)-UB-165. J. Med. Chem. 2002, 45, 3235-3245.
    • (2002) J. Med. Chem. , vol.45 , pp. 3235-3245
    • Sharpless, C.G.V.1    Karig, G.2    Simpson, G.L.3    Spencer, J.A.4    Wright, E.5    Milar, N.S.6    Wonnacott, S.7    Gallagher, T.8
  • 12
    • 0022214795 scopus 로고
    • Synthetic and conformational studies on anatoxin-a: A potent acetylcholine agonist
    • Koskinen, A. M. P.; Rapoport, H. Synthetic and Conformational Studies on Anatoxin-a: A Potent Acetylcholine Agonist. J. Med. Chem. 1985, 28, 1301-1309.
    • (1985) J. Med. Chem. , vol.28 , pp. 1301-1309
    • Koskinen, A.M.P.1    Rapoport, H.2
  • 14
    • 0031053794 scopus 로고    scopus 로고
    • Synthesis and nicotinic activity of epiboxidine: An isoxazole analogue of epibatidine
    • Badio, B.; Garaffo, H. M.; Plummer, C. V.; Padgett, W. L.; Daly, J. W. Synthesis and Nicotinic Activity of Epiboxidine: An Isoxazole Analogue of Epibatidine. Eur. J. Pharmacol. 1997, 321, 189-194.
    • (1997) Eur. J. Pharmacol. , vol.321 , pp. 189-194
    • Badio, B.1    Garaffo, H.M.2    Plummer, C.V.3    Padgett, W.L.4    Daly, J.W.5
  • 15
    • 0035804307 scopus 로고    scopus 로고
    • exo-2-(Pyridazin-4-yl)-7-azabicyclo-[2.2.1]heptanes: Syntheses and nicotinic acetylcholine receptor agonist activity of potent pyridazine analogues of (±)-Epibatidine
    • Che, D.; Wegge, T.; Stubbs, M. T.; Seitz, G.; Meier, H.; Methfessel, C. exo-2-(Pyridazin-4-yl)-7-azabicyclo-[2.2.1]heptanes: Syntheses and Nicotinic Acetylcholine Receptor Agonist Activity of Potent Pyridazine Analogues of (±)-Epibatidine. J. Med. Chem. 2001, 44, 47-57.
    • (2001) J. Med. Chem. , vol.44 , pp. 47-57
    • Che, D.1    Wegge, T.2    Stubbs, M.T.3    Seitz, G.4    Meier, H.5    Methfessel, C.6
  • 16
    • 0037858536 scopus 로고    scopus 로고
    • Ph.D. Thesis, Philipps-University of Marburg
    • Wegge, T. Ph.D. Thesis, Philipps-University of Marburg, 2001.
    • (2001)
    • Wegge, T.1
  • 17
    • 0034918683 scopus 로고    scopus 로고
    • Syntheses and evaluation of halogenated cytisine derivatives and of bioisosteric thiocytisine as potent and selective nAChR ligands
    • Imming, P.; Klaperski, P.; Stubbs, M. T.; Seitz, G.; Gündisch, D. Syntheses and Evaluation of Halogenated Cytisine Derivatives and of Bioisosteric Thiocytisine as Potent and Selective nAChR Ligands. Eur. J. Med. Chem. 2001, 36, 375-388.
    • (2001) Eur. J. Med. Chem. , vol.36 , pp. 375-388
    • Imming, P.1    Klaperski, P.2    Stubbs, M.T.3    Seitz, G.4    Gündisch, D.5
  • 18
    • 0037186458 scopus 로고    scopus 로고
    • Synthesis and nicotinic binding studies on enantiopure diazine analogues of the novel (2-Chloro-5-pyridyl)-9azabicyclo[4.2.1]non-2-ene UB-165
    • and references therein
    • Gohlke, H.; Gündisch, D.; Schwarz, S.; Tilotta, M. C.; Seitz, G.; Wegge, T. Synthesis and Nicotinic Binding Studies on Enantiopure Diazine Analogues of the Novel (2-Chloro-5-pyridyl)-9azabicyclo[4.2.1]non-2-ene UB-165. J. Med. Chem. 2002, 45, 1064-1072 and references therein.
    • (2002) J. Med. Chem. , vol.45 , pp. 1064-1072
    • Gohlke, H.1    Gündisch, D.2    Schwarz, S.3    Tilotta, M.C.4    Seitz, G.5    Wegge, T.6
  • 19
    • 0037858529 scopus 로고    scopus 로고
    • Ph.D. Thesis, Philipps-University of Marburg
    • Schwarz, S. Ph.D. Thesis, Philipps-University of Marburg, 2002.
    • (2002)
    • Schwarz, S.1
  • 20
    • 0034842156 scopus 로고    scopus 로고
    • Synthesis and evaluation of diazine containing bioisosteres of (-)-Ferruginine as ligands for nicotinic acetylcholine receptors
    • Gündisch, D.; Harms, K.; Schwarz, S.; Seitz, G.; Stubbs, M. T.; Wegge, T. Synthesis and Evaluation of Diazine Containing Bioisosteres of (-)-Ferruginine as Ligands for Nicotinic Acetylcholine Receptors. Bioorg. Med. Chem. 2001, 9, 2683-2691.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 2683-2691
    • Gündisch, D.1    Harms, K.2    Schwarz, S.3    Seitz, G.4    Stubbs, M.T.5    Wegge, T.6
  • 21
    • 0036132017 scopus 로고    scopus 로고
    • Syntheses and evaluation of pyridazine and pyrimidine containing bioisosteres of (±)-Pyrido[3.4-b]homotropane and Pyrido[3.4-b]tropane as novel nAChR ligands
    • Gündisch, D.; Kämpchen, T.; Schwarz, S.; Seitz, G.; Siegl, J.; Wegge, T. Syntheses and Evaluation of Pyridazine and Pyrimidine Containing Bioisosteres of (±)-Pyrido[3.4-b]homotropane and Pyrido[3.4-b]tropane as Novel nAChR Ligands. Bioorg. Med. Chem. 2002, 10, 1-9.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 1-9
    • Gündisch, D.1    Kämpchen, T.2    Schwarz, S.3    Seitz, G.4    Siegl, J.5    Wegge, T.6
  • 22
    • 0038535040 scopus 로고    scopus 로고
    • Ph.D. Thesis, Philipps -University of Marburg
    • Stehl, A. Ph.D. Thesis, Philipps -University of Marburg, 2002.
    • (2002)
    • Stehl, A.1
  • 25
    • 0038184150 scopus 로고    scopus 로고
    • An improved synthesis and in vitro evaluation of Quinuclidin-2-ene based ligands for the nicotinic acetylcholine receptor
    • in press
    • Seifert, S.; Gündisch, D.; Tilotta, M. C.; Seitz, G. An Improved Synthesis and In Vitro Evaluation of Quinuclidin-2-ene Based Ligands for the Nicotinic Acetylcholine Receptor. Pharmazie 2003, 58, in press.
    • (2003) Pharmazie , vol.58
    • Seifert, S.1    Gündisch, D.2    Tilotta, M.C.3    Seitz, G.4
  • 26
    • 0022485091 scopus 로고
    • The ensemble approach to distance geometry: Application to the nicotinic pharmacophore
    • Sheridan, R. P.; Nilakantan, R.; Dixon, J. S.; Venkataraghavan, R. The Ensemble Approach to Distance Geometry: Application to the Nicotinic Pharmacophore. J. Med. Chem. 1986, 29, 899-906.
    • (1986) J. Med. Chem. , vol.29 , pp. 899-906
    • Sheridan, R.P.1    Nilakantan, R.2    Dixon, J.S.3    Venkataraghavan, R.4
  • 27
    • 0024455877 scopus 로고
    • Relations between structure and nicotine-like activity: X-ray crystal structure analysis of (-)Cytisine and (-)-Lobeline hydrochloride and a comparison with (-)-Nicotine and other nicotine-like compounds
    • Barlow, R. B.; Johnson, O. Relations Between Structure and Nicotine-Like Activity: X-ray Crystal Structure Analysis of (-)Cytisine and (-)-Lobeline Hydrochloride and a Comparison with (-)-Nicotine and other Nicotine-Like Compounds. J. Pharmacol. 1989, 98, 799-808.
    • (1989) J. Pharmacol. , vol.98 , pp. 799-808
    • Barlow, R.B.1    Johnson, O.2
  • 30
    • 0000949429 scopus 로고
    • Epibatidine-aided studies toward definition of a nicotine receptor pharmacophore
    • Glennon, R. A.; Herndon, J. L.; Dukat, M. Epibatidine-Aided Studies Toward Definition of a Nicotine Receptor Pharmacophore. Med. Chem. Res. 1994, 4, 461-473.
    • (1994) Med. Chem. Res. , vol.4 , pp. 461-473
    • Glennon, R.A.1    Herndon, J.L.2    Dukat, M.3
  • 31
    • 0035902009 scopus 로고    scopus 로고
    • Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors
    • Brejc, K.; van Dijk, W. J.; Klaassen, R. V.; Schuurmans, M.; van der Oost, J.; Smit, A. B.; Sixma, T. K. Crystal Structure of an ACh-Binding Protein Reveals the Ligand-Binding Domain of Nicotinic Receptors. Nature 2001, 411, 269-276.
    • (2001) Nature , vol.411 , pp. 269-276
    • Brejc, K.1    Van Dijk, W.J.2    Klaassen, R.V.3    Schuurmans, M.4    Van der Oost, J.5    Smit, A.B.6    Sixma, T.K.7
  • 32
    • 0037022640 scopus 로고    scopus 로고
    • Models of the extracellular domain of the nicotinic receptors and of agonistand Ca2+-binding sites
    • Le Novère, N.; Grutter, T.; Changeux, J.-P. Models of the Extracellular Domain of the Nicotinic Receptors and of Agonistand Ca2+-Binding Sites. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 3210-3215.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 3210-3215
    • Le Novère, N.1    Grutter, T.2    Changeux, J.-P.3
  • 34
    • 0036230488 scopus 로고    scopus 로고
    • Ligands of neuronal nicotinic acetylcholine receptor (nAChR): Inferences from the Hansch and 3-D Quantitative Structure-Activity Relationship (QSAR) models
    • Nicolotti, O.; Pellegrini-Callace, M.; Altomare, C.; Carotti, A.; Carrieri, A.; Sanz, F. Ligands of Neuronal Nicotinic Acetylcholine Receptor (nAChR): Inferences from the Hansch and 3-D Quantitative Structure -Activity Relationship (QSAR) Models. Curr. Med. Chem. 2002, 9, 1-29.
    • (2002) Curr. Med. Chem. , vol.9 , pp. 1-29
    • Nicolotti, O.1    Pellegrini-Callace, M.2    Altomare, C.3    Carotti, A.4    Carrieri, A.5    Sanz, F.6
  • 35
    • 0037072311 scopus 로고    scopus 로고
    • Cation-π-interactions in ligand recognition by serotonergic (5-HT3A) and nicotinic acetylcholine receptors: The anomalous binding properties of nicotine
    • Beene, D. L.; Brandt, G. S.; Zhong, W.; Zacharias, N. M.; Lester, H. A.; Dougherty, D. A. Cation-π-Interactions in Ligand Recognition by Serotonergic (5-HT3A) and Nicotinic Acetylcholine Receptors: The Anomalous Binding Properties of Nicotine. Biochemistry 2002, 41, 10262-10269.
    • (2002) Biochemistry , vol.41 , pp. 10262-10269
    • Beene, D.L.1    Brandt, G.S.2    Zhong, W.3    Zacharias, N.M.4    Lester, H.A.5    Dougherty, D.A.6
  • 37
    • 0023751431 scopus 로고
    • Comparative Molecular Field Analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins
    • Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5959-5967
    • Cramer R.D. III1    Patterson, D.E.2    Bunce, J.D.3
  • 38
    • 0027944195 scopus 로고
    • Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity
    • Klebe, G.; Abraham, U.; Mietzner, T. Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules to Correlate and Predict Their Biological Activity. J. Med. Chem. 1994, 37, 4130-4146.
    • (1994) J. Med. Chem. , vol.37 , pp. 4130-4146
    • Klebe, G.1    Abraham, U.2    Mietzner, T.3
  • 39
    • 0033022163 scopus 로고    scopus 로고
    • Comparative Molecular Similarity Indices Analysis (CoMSIA) To study hydrogen-bonding properties and to score combinatorial libraries
    • Klebe, G.; Abraham, U. Comparative Molecular Similarity Indices Analysis (CoMSIA) To Study Hydrogen-Bonding Properties and To Score Combinatorial Libraries. J. Comput.-Aided Mol. Des. 1999, 13, 1-10.
    • (1999) J. Comput.-Aided Mol. Des. , vol.13 , pp. 1-10
    • Klebe, G.1    Abraham, U.2
  • 40
    • 0037920567 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship analyses using comparative molecular field analysis and comparative molecular similarity indices analysis to elucidate selectivity differences of inhibitors binding to Trypsin, Thrombin, and Factor Xa
    • Böhm, M.; Stürzebecher, J.; Klebe, G. Three-Dimensional Quantitative Structure-Activity Relationship Analyses Using Comparative Molecular Field Analysis and Comparative Molecular Similarity Indices Analysis to Elucidate Selectivity Differences of Inhibitors Binding to Trypsin, Thrombin, and Factor Xa. J. Med. Chem. 1999, 42, 458-477.
    • (1999) J. Med. Chem. , vol.42 , pp. 458-477
    • Böhm, M.1    Stürzebecher, J.2    Klebe, G.3
  • 42
    • 0003476930 scopus 로고    scopus 로고
    • Critical review of recent CoMFA applications
    • Kubinyi, H., Folkers, G., Martin, Y. C., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands
    • Kim, K. H.; Greco, G.; Novellino, A. Critical Review of Recent CoMFA Applications. In 3D QSAR in Drug Design; Kubinyi, H., Folkers, G., Martin, Y. C., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1998; Vol. 3.
    • (1998) 3D QSAR in Drug Design , vol.3
    • Kim, K.H.1    Greco, G.2    Novellino, A.3
  • 44
    • 0034616241 scopus 로고    scopus 로고
    • A new efficient synthetic route to enantiopure (+)-Anatoxin-a from (-)-Cocaine hydrochloride
    • and references therein
    • Wegge, T.; Schwarz, S.; Seitz, G. A New and Efficient Synthetic Route to Enantiopure (+)-Anatoxin-a from (-)-Cocaine Hydrochloride. Tetrahedron: Asymmetry 2000, 11, 1405-1410 and references therein.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1405-1410
    • Wegge, T.1    Schwarz, S.2    Seitz, G.3
  • 46
    • 0025390935 scopus 로고
    • MOPAC: A semiempirical molecular orbital program
    • Stewart, J. J. MOPAC: A Semiempirical Molecular Orbital Program. J. Comput. -Aided Mol. Des. 1990, 4, 1-105.
    • (1990) J. Comput. -Aided Mol. Des. , vol.4 , pp. 1-105
    • Stewart, J.J.1
  • 48
    • 0032153072 scopus 로고    scopus 로고
    • RigFit: A new approach to superimposing ligand molecules
    • Lemmen, C.; Hiller, C.; Lengauer, T. RigFit: A New Approach to Superimposing Ligand Molecules. J. Comput.-Aided Mol. Des. 1998, 12, 491-502.
    • (1998) J. Comput.-Aided Mol. Des. , vol.12 , pp. 491-502
    • Lemmen, C.1    Hiller, C.2    Lengauer, T.3
  • 49
    • 0033020898 scopus 로고    scopus 로고
    • Methodological developments and strategies for a fast flexible superposition of drug-size molecules
    • Klebe, G.; Mietzner, T.; Weber, F. Methodological Developments and Strategies for a Fast Flexible Superposition of Drug-Size Molecules. J. Comput.-Aided Mol. Des. 1999, 13, 35-49.
    • (1999) J. Comput.-Aided Mol. Des. , vol.13 , pp. 35-49
    • Klebe, G.1    Mietzner, T.2    Weber, F.3
  • 50
    • 44949267284 scopus 로고
    • An alternative method for the alignment of molecular structures: Maximizing electrostatic and steric overlap
    • Kearsley, S. K.; Smith, G. M. An Alternative Method for the Alignment of Molecular Structures: Maximizing Electrostatic and Steric Overlap. Tetrahedron Comput. Methodol. 1990, 3, 615-633.
    • (1990) Tetrahedron Comput. Methodol. , vol.3 , pp. 615-633
    • Kearsley, S.K.1    Smith, G.M.2
  • 51
    • 0031531210 scopus 로고    scopus 로고
    • Theoretical and practical aspects of three-dimensional quantitative structure-activity relationships
    • Lipkowitz, K. B., Toyd, D. B., Eds.; Wiley-VCH: New York
    • Oprea, T. I.; Waller, C. L. Theoretical and Practical Aspects of Three-Dimensional Quantitative Structure- Activity Relationships. In Reviews in Computational Chemistry; Lipkowitz, K. B., Toyd, D. B., Eds.; Wiley-VCH: New York, 1997; Vol. 11.
    • (1997) Reviews in Computational Chemistry , vol.11
    • Oprea, T.I.1    Waller, C.L.2
  • 53
    • 0001681052 scopus 로고
    • The collinearity problem in linear regression. The partial least squares approach to generalized inverses
    • Wold, S.; Ruhe, A.; Wold, H.; Dunn, W. J., III. The Collinearity Problem in Linear Regression. The Partial Least Squares Approach to Generalized Inverses. SIAM J. Sci. Statist. Comput. 1984, 5, 735-743.
    • (1984) SIAM J. Sci. Statist. Comput. , vol.5 , pp. 735-743
    • Wold, S.1    Ruhe, A.2    Wold, H.3    Dunn W.J. III4
  • 54
    • 0024154259 scopus 로고
    • Multivariate data analysis and experimental design in biochemical research
    • Stable, L.; Wold, S. Multivariate Data Analysis and Experimental Design in Biochemical Research. Prog. Med. Chem. 1988, 25, 291-338.
    • (1988) Prog. Med. Chem. , vol.25 , pp. 291-338
    • Stable, L.1    Wold, S.2
  • 55
    • 0027672324 scopus 로고
    • Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA
    • Bush, B. L.; Nachbar, R. B., Jr. Sample-Distance Partial Least Squares: PLS Optimized for Many Variables, with Application to CoMFA. J. Comput.-Aided Mol. Des. 1993, 7, 587-619.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 587-619
    • Bush, B.L.1    Nachbar R.B., Jr.2
  • 56
    • 0035544084 scopus 로고    scopus 로고
    • 6-Substituted 2-Azabicyclo[2.2.1]hept-5-enes by nitrogen-directed radical rearrangement: Synthesis of an epibatidine analogue with high binding affinity at the nicotinic acetylcholine receptor
    • Hodgson, D. M.; Maxwell, C. R.; Wisedale, R.; Matthews, I. R.; Carpenter, K. J.; Dickenson, A. H.; Wonnacott, S. 6-Substituted 2-Azabicyclo[2.2.1]hept-5-enes by Nitrogen-Directed Radical Rearrangement: Synthesis of an Epibatidine Analogue with High Binding Affinity at the Nicotinic Acetylcholine Receptor. J. Chem. Soc., Perkin Trans. 1 2001, 3150-3158.
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 3150-3158
    • Hodgson, D.M.1    Maxwell, C.R.2    Wisedale, R.3    Matthews, I.R.4    Carpenter, K.J.5    Dickenson, A.H.6    Wonnacott, S.7
  • 57
    • 0038196297 scopus 로고    scopus 로고
    • note
    • The contour levels of CoMFA contour maps are given normally in kcal/mol. Because the CoMSIA similarity indices fields are defined in arbitrary units, they do not correspond to any potential describing different partitions of molecular interactions such as CoMFA. Consequently, the CoMSIA contour levels are given without any units.
  • 58
    • 0030947528 scopus 로고    scopus 로고
    • Evidence for spare nicotinic acetylcholine receptors and a β4 subunit in bovine adrenal chromaffin cells: Studies using bromoacetylcholine, epibatidine, cytisine and mAb35
    • Wenger, B. W.; Bryant, D. L.; Boyd, R. T.; McKay, D. B. Evidence for Spare Nicotinic Acetylcholine Receptors and a β4 Subunit in Bovine Adrenal Chromaffin Cells: Studies Using Bromoacetylcholine, Epibatidine, Cytisine and mAb35. J. Pharmacol. Exp. Ther. 1997, 281, 905-913.
    • (1997) J. Pharmacol. Exp. Ther. , vol.281 , pp. 905-913
    • Wenger, B.W.1    Bryant, D.L.2    Boyd, R.T.3    McKay, D.B.4
  • 60
    • 0031958663 scopus 로고    scopus 로고
    • Differential agonist inhibition identifies multiple epibatidine binding sites in mouse brain
    • Marks, M. J.; Smith, K. W.; Collins, A. C. Differential Agonist Inhibition Identifies Multiple Epibatidine Binding Sites in Mouse Brain. J. Pharmacol. Exp. Ther. 1998, 285, 377-386.
    • (1998) J. Pharmacol. Exp. Ther. , vol.285 , pp. 377-386
    • Marks, M.J.1    Smith, K.W.2    Collins, A.C.3
  • 62
    • 0031780511 scopus 로고    scopus 로고
    • Agonist-induced upregulation of α4β2 nicotinic acetylcholine receptors in M10 cells: Pharmacological and spatial definition
    • Whiteaker, P.; Sharples, C. G.; Wonnacott, S. Agonist-Induced Upregulation of α4β2 Nicotinic Acetylcholine Receptors in M10 cells: Pharmacological and Spatial Definition. Mol. Pharmacol. 1998, 53, 950-962.
    • (1998) Mol. Pharmacol. , vol.53 , pp. 950-962
    • Whiteaker, P.1    Sharples, C.G.2    Wonnacott, S.3
  • 64
    • 2742568471 scopus 로고    scopus 로고
    • Tetraphosphorus decasulfide, revival of an old thionating agent
    • Hartke, K.; Gerber, H. D. Tetraphosphorus Decasulfide, Revival of an Old Thionating Agent. J. Prakt. Chem. / Chem.-Ztg. 1996, 338, 763-765.
    • (1996) J. Prakt. Chem./Chem.-Ztg. , vol.338 , pp. 763-765
    • Hartke, K.1    Gerber, H.D.2
  • 65
    • 0344298556 scopus 로고    scopus 로고
    • Synthesis of (±)-Epibatidine and its analogues
    • Bai, D.; Xu, R.; Chu, C.; Zhu, X. Synthesis of (±)-Epibatidine and Its Analogues. J. Org. Chem. 1996, 61, 4600-4606.
    • (1996) J. Org. Chem. , vol.61 , pp. 4600-4606
    • Bai, D.1    Xu, R.2    Chu, C.3    Zhu, X.4
  • 67
    • 84985570392 scopus 로고
    • Palladium-catalyzed coupling reactions of organic electrophiles with organo-stannanes
    • Stille, J. K. Palladium-Catalyzed Coupling Reactions of Organic Electrophiles with Organo-Stannanes. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 508-524
    • Stille, J.K.1
  • 68
    • 33751385493 scopus 로고
    • Palladium-catalyzed cross-coupling reaction of organoboron compounds with organic triflates
    • Oh-e, T.; Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reaction of Organoboron Compounds with Organic Triflates. J. Org. Chem. 1993, 58, 2201-2208.
    • (1993) J. Org. Chem. , vol.58 , pp. 2201-2208
    • Oh-e, T.1    Miyaura, N.2    Suzuki, A.3
  • 69
    • 0037061650 scopus 로고    scopus 로고
    • Development of new hydrogen-bond descriptors and their application to comparative molecular field analyses
    • Böhm, M.; Klebe, G. Development of New Hydrogen-Bond Descriptors and Their Application to Comparative Molecular Field Analyses. J. Med. Chem. 2002, 45, 1585-1597.
    • (2002) J. Med. Chem. , vol.45 , pp. 1585-1597
    • Böhm, M.1    Klebe, G.2
  • 70
    • 0037075132 scopus 로고    scopus 로고
    • CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: Exploration of a binding mode at the active site
    • Boulamwini, J. K.; Assefa, H. CoMFA and CoMSIA 3D QSAR and Docking Studies on Conformationally-Restrained Cinnamoyl HIV-1 Integrase Inhibitors: Exploration of a Binding Mode at the Active Site. J. Med. Chem. 2002, 45, 841-852.
    • (2002) J. Med. Chem. , vol.45 , pp. 841-852
    • Boulamwini, J.K.1    Assefa, H.2
  • 71
    • 0029745052 scopus 로고    scopus 로고
    • Cation-π interactions in aromatics of biological and medicinal interest: Electrostatic potential surfaces as a useful qualitative guide
    • Mecozzi, S.; West, A. P., Jr.; Dougherty, D. A. Cation-π Interactions in Aromatics of Biological and Medicinal Interest: Electrostatic Potential Surfaces as a Useful Qualitative Guide. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10566-10571.
    • (1996) Proc. Natl. Acad. Sci. U.S.A. , vol.93 , pp. 10566-10571
    • Mecozzi, S.1    West A.P., Jr.2    Dougherty, D.A.3
  • 72
    • 0000826617 scopus 로고    scopus 로고
    • Hydrogen bonding properties of oxygen and nitrogen acceptors in aromatic heterocycles
    • Nobeli, I.; Price, S. L.; Lommerse, J. P. M.; Taylor, R. Hydrogen Bonding Properties of Oxygen and Nitrogen Acceptors in Aromatic Heterocycles. J. Comput. Chem. 1997, 18, 2060-2074.
    • (1997) J. Comput. Chem. , vol.18 , pp. 2060-2074
    • Nobeli, I.1    Price, S.L.2    Lommerse, J.P.M.3    Taylor, R.4
  • 73
    • 0030033588 scopus 로고    scopus 로고
    • Cation-π interactions in chemistry and biology: A new view of Benzene, Phe, Tyr, and Trp
    • Dougherty, D. A. Cation-π Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp. Science 1996, 271, 163-168.
    • (1996) Science , vol.271 , pp. 163-168
    • Dougherty, D.A.1
  • 75
    • 0034213308 scopus 로고    scopus 로고
    • Novel potent ligands for the central nicotinic acetylcholine receptor: Synthesis, receptor binding, and 3D QSAR analyses
    • Nielsen, S. F.; Ostergaard Nielsen, E.; Olsen, G. M.; Liljefors, T.; Peters, D. Novel Potent Ligands for the Central Nicotinic Acetylcholine Receptor: Synthesis, Receptor Binding, and 3D QSAR Analyses. J. Med. Chem. 2000, 43, 2217- 2226.
    • (2000) J. Med. Chem. , vol.43 , pp. 2217-2226
    • Nielsen, S.F.1    Ostergaard Nielsen, E.2    Olsen, G.M.3    Liljefors, T.4    Peters, D.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.