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Volumn 42, Issue 9, 1999, Pages 1537-1545

Comparative molecular field analysis of hydantoin binding to the neuronal voltage-dependent sodium channel

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXY ALPHA PHENYLAMIDE; ANILIDE; CARBAMAZEPINE; HYDANTOIN DERIVATIVE; SODIUM CHANNEL; UNCLASSIFIED DRUG;

EID: 0033529093     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980556l     Document Type: Article
Times cited : (62)

References (37)
  • 1
    • 0020334077 scopus 로고
    • 3H]-batrachotoxinin A 20-α-benzoate to sodium channels by the anticonvulsant drugs diphenylhydantoin and carbamazepine
    • 3H]-Batrachotoxinin A 20-α-Benzoate to Sodium Channels by the Anticonvulsant Drugs Diphenylhydantoin and Carbamazepine. Mol. Pharmacol. 1982, 22, 627-635.
    • (1982) Mol. Pharmacol. , vol.22 , pp. 627-635
    • Willow, M.1    Catterall, W.A.2
  • 2
    • 0031052522 scopus 로고    scopus 로고
    • Effects of log P and phenyl ring conformation on the binding of 5-phenylhydantoins to the voltage-dependent sodium channel
    • Brown, M. L.; Brown, G. B.; Brouillette, W. J. Effects of Log P and Phenyl Ring Conformation on the Binding of 5-Phenylhydantoins to the Voltage-Dependent Sodium Channel. J. Med. Chem. 1997, 40, 602-607.
    • (1997) J. Med. Chem. , vol.40 , pp. 602-607
    • Brown, M.L.1    Brown, G.B.2    Brouillette, W.J.3
  • 3
    • 0028028227 scopus 로고
    • Bicyclic hydantoins with bridgehead nitrogen. Comparison of anticonvulsant activities with binding to the neuronal voltage-dependent sodium channel
    • Brouillette, W. J.; Jestkov, V. P.; Brown, M. L.; Aktar, M. S.; Delorey, T. M.; Brown, G. B. Bicyclic Hydantoins with Bridgehead Nitrogen. Comparison of Anticonvulsant Activities with Binding to the Neuronal Voltage-Dependent Sodium Channel. J. Med. Chem. 1994, 37, 3289-3293.
    • (1994) J. Med. Chem. , vol.37 , pp. 3289-3293
    • Brouillette, W.J.1    Jestkov, V.P.2    Brown, M.L.3    Aktar, M.S.4    Delorey, T.M.5    Brown, G.B.6
  • 4
    • 0027008386 scopus 로고
    • 3H]phenytoin identifies a novel anticonvulsant-binding domain on voltage-dependent sodium channels
    • 3H]Phenytoin Identifies a Novel Anticonvulsant-Binding Domain on Voltage-Dependent Sodium Channels. Mol. Pharmacol. 1992, 42, 1097-1103.
    • (1992) Mol. Pharmacol. , vol.42 , pp. 1097-1103
    • Francis, J.1    Burnham, W.M.2
  • 5
    • 0026095969 scopus 로고
    • Blockade of cardiac sodium channels by amitriptyline and diphenylhydantoin. Evidence for two use-dependent binding sites
    • Barber, M. J.; Starmer, C. F.; Grant, A. O. Blockade of Cardiac Sodium Channels by Amitriptyline and Diphenylhydantoin. Evidence for Two Use-dependent Binding Sites. Cir. Res. 1991, 69, 677-696.
    • (1991) Cir. Res. , vol.69 , pp. 677-696
    • Barber, M.J.1    Starmer, C.F.2    Grant, A.O.3
  • 6
    • 0026331401 scopus 로고
    • Comparative molecular field analysis on a set of muscurinic agents
    • Greco, G.; Novellino, C. S.; Vittora, A. Comparative Molecular Field Analysis on a Set of Muscurinic Agents. QSAR 1991, 10, 289-299.
    • (1991) QSAR , vol.10 , pp. 289-299
    • Greco, G.1    Novellino, C.S.2    Vittora, A.3
  • 7
    • 0027615806 scopus 로고
    • Use of the hydrogen bond potential function in a comparative molecular field analysis (CoMFA) on a set of benzodiazepines
    • Kim, K H.; Greco, G.; Novellino, E.; Silipa, C.; Vittoria, A. Use of the Hydrogen Bond Potential Function in a Comparative Molecular Field Analysis (CoMFA) on a Set of Benzodiazepines. J. Comput.-Aided Mol. Des. 1993, 7, 263-280.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 263-280
    • Kim, K.H.1    Greco, G.2    Novellino, E.3    Silipa, C.4    Vittoria, A.5
  • 8
    • 0028037156 scopus 로고
    • Comparative molecular field analysis model for 6-arylpyrrolo[2,1-d][1,5]-benzothiazepines binding selectively to the mitochondrial benzodiazepine receptor
    • Giovanni, G.; Ettore, N.; Fiorini, I.; Nacci, B.; Campiani, G.; Ciani, S. M.; Garofalo, A.; Bernasconii, P.; Mennini, T. Comparative Molecular Field Analysis Model for 6-Arylpyrrolo[2,1-d][1,5]-Benzothiazepines Binding Selectively to the Mitochondrial Benzodiazepine Receptor. J. Med. Chem. 1994, 37, 4100-4108.
    • (1994) J. Med. Chem. , vol.37 , pp. 4100-4108
    • Giovanni, G.1    Ettore, N.2    Fiorini, I.3    Nacci, B.4    Campiani, G.5    Ciani, S.M.6    Garofalo, A.7    Bernasconii, P.8    Mennini, T.9
  • 9
    • 0027233914 scopus 로고
    • Synthetic and computer-assisted analysis of the structural requirements for selective, high-affinity ligand binding to diazepam-insensitive benzodiazepine receptors
    • Wong, G.; Koehler, K. F.; Skolnick, P.; Gu, Z.-Q.; Ananthan, P.; Schönholzer, W.; Hyunkeler, W.; Zhang, W.; Cook, M. Synthetic and Computer-Assisted Analysis of the Structural Requirements for Selective, High-Affinity Ligand Binding to Diazepam-Insensitive Benzodiazepine Receptors. J. Med. Chem. 1993, 36, 1820-1830.
    • (1993) J. Med. Chem. , vol.36 , pp. 1820-1830
    • Wong, G.1    Koehler, K.F.2    Skolnick, P.3    Gu, Z.-Q.4    Ananthan, P.5    Schönholzer, W.6    Hyunkeler, W.7    Zhang, W.8    Cook, M.9
  • 11
    • 0000779389 scopus 로고
    • Analysis of the structure activity relationships of Sigma Ligands
    • Ablordeppy, S. Y.; El-Ashmaway, M. B.; Glennon, R. A. Analysis of the Structure Activity Relationships of Sigma Ligands. Med. Chem. Res. 1991, 1, 425-438.
    • (1991) Med. Chem. Res. , vol.1 , pp. 425-438
    • Ablordeppy, S.Y.1    El-Ashmaway, M.B.2    Glennon, R.A.3
  • 12
    • 0025827583 scopus 로고
    • Modeling the cannabinoid receptor: A three-dimensional quantative structure activity analysis
    • Thomas, B. F.; Compton, B. R. M.; Semus, S. F. Modeling the Cannabinoid Receptor: A Three-Dimensional Quantative Structure Activity Analysis. Mol. Pharmacol. 1991, 40, 656-661.
    • (1991) Mol. Pharmacol. , vol.40 , pp. 656-661
    • Thomas, B.F.1    Compton, B.R.M.2    Semus, S.F.3
  • 13
    • 0344683102 scopus 로고
    • A computer graphic investigation into the structural requirements for interaction with the putative cannabinoid receptor site
    • Semus, S. F. A Computer Graphic Investigation into the Structural Requirements for Interaction with the Putative Cannabinoid Receptor Site. Med. Chem. Res. 1991, 7, 454-460.
    • (1991) Med. Chem. Res. , vol.7 , pp. 454-460
    • Semus, S.F.1
  • 14
    • 0027253558 scopus 로고
    • Structure-function correlations for calcium binding and calcium channel activities based on 3-dimensional models of human annexins I, II, III, V, VII
    • Chen, J. M.; Sheldon, A. Structure-Function Correlations for Calcium Binding and Calcium Channel Activities Based on 3-Dimensional Models of Human Annexins I, II, III, V, VII. Biomol. Struct. Dynam. 1993, 10, 1067-1089.
    • (1993) Biomol. Struct. Dynam. , vol.10 , pp. 1067-1089
    • Chen, J.M.1    Sheldon, A.2
  • 16
    • 0027278101 scopus 로고
    • Binding site modeling of the muscarinic M1 receptor: A combination of homology-based and indirect approaches
    • Nordvall, G.; Hacksell, U. Binding Site Modeling of the Muscarinic M1 Receptor: A Combination of Homology-Based and Indirect Approaches. J. Med. Chem. 1993, 36, 967-976.
    • (1993) J. Med. Chem. , vol.36 , pp. 967-976
    • Nordvall, G.1    Hacksell, U.2
  • 17
    • 0027968806 scopus 로고
    • Synthesis, ligand-binding and QSAR (CoMFA and classical) study of 3β-(3′-substituted phenyl), 3β-(4′-substituted phenyl), 3β-(3′,4′-disubstituted phenyl)tropane-2β-carboxylic acid methyl-esters
    • Caroll, F. I.; Mascrella, S. W.; Kuzemko, M. A.; Goa, Y. G.; Abraham, P.; Lewin, A. H.; Boja, J. W.; Kuhar, M. J. Synthesis, Ligand-Binding and QSAR (CoMFA and Classical) Study of 3β-(3′-Substituted Phenyl), 3β-(4′-Substituted Phenyl), 3β-(3′,4′-Disubstituted Phenyl)tropane-2β-Carboxylic Acid Methyl-Esters. J. Med. Chem. 1994, 37, 2865-2873.
    • (1994) J. Med. Chem. , vol.37 , pp. 2865-2873
    • Caroll, F.I.1    Mascrella, S.W.2    Kuzemko, M.A.3    Goa, Y.G.4    Abraham, P.5    Lewin, A.H.6    Boja, J.W.7    Kuhar, M.J.8
  • 18
    • 84912099528 scopus 로고
    • 1A receptor ligands by the method of comparative molecular field analysis
    • 1A Receptor Ligands by the Method of Comparative Molecular Field Analysis. J. Comput. Chem. 1993, 14, 237-245.
    • (1993) J. Comput. Chem. , vol.14 , pp. 237-245
    • Agarwal, A.1    Taylor, E.W.2
  • 19
    • 0027613239 scopus 로고
    • Inhibitors of prolyl endopeptidase: Characterization of the pharmacophoric pattern using conformational analysis and 3D-QSAR
    • Langer, T.; Wermuth, C. G. Inhibitors of Prolyl Endopeptidase: Characterization of the Pharmacophoric Pattern Using Conformational Analysis and 3D-QSAR. J. Comput.-Aided Mol. Des. 1993, 7, 253-262.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 253-262
    • Langer, T.1    Wermuth, C.G.2
  • 21
    • 0027551098 scopus 로고
    • CoMFA validation of the superposition of six classes of compounds which block GABA receptors non-competitively
    • Calder, J. A.; Wyatt, J. A.; Frenkel, D. A.; Casida, J. E. CoMFA Validation of the Superposition of Six Classes of Compounds Which Block GABA Receptors Non-Competitively. J. Comput.-Aided Mol. Des. 1993, 7, 45-60.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 45-60
    • Calder, J.A.1    Wyatt, J.A.2    Frenkel, D.A.3    Casida, J.E.4
  • 22
    • 0000708326 scopus 로고
    • Conformational analysis of the sodium channel modulator, brevetoxin A. Comparison with brevetoxin B conformations, and a hypothesis about the common pharmacophore of the "site 5" toxins
    • Rein, K S.; Baden, D. G.; Gawley, R. E. Conformational Analysis of the Sodium Channel Modulator, Brevetoxin A. Comparison with Brevetoxin B Conformations, and a Hypothesis About the Common Pharmacophore of the "Site 5" Toxins. J. Org. Chem. 1994, 59, 2101-2106.
    • (1994) J. Org. Chem. , vol.59 , pp. 2101-2106
    • Rein, K.S.1    Baden, D.G.2    Gawley, R.E.3
  • 23
    • 84988115618 scopus 로고
    • Validation of the general purpose tripos 5.2 force field
    • Clark, M. D.; Cramer, R. D., III; Opdenbosch, N. V. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
    • (1989) J. Comput. Chem. , vol.10 , pp. 982-1012
    • Clark, M.D.1    Cramer R.D. III2    3    Opdenbosch, N.V.4
  • 24
    • 0025084679 scopus 로고
    • Sodium channel binding and anticonvulsant activities of hydantoins containing conformationally constrained 5-phenyl substituents
    • Brouillette, W. J.; Brown, G. B.; Delorey, T. M.; Liang, G. Sodium Channel Binding and Anticonvulsant Activities of Hydantoins Containing Conformationally Constrained 5-Phenyl Substituents. J. Pharm. Sci. 1990, 79, 871-874.
    • (1990) J. Pharm. Sci. , vol.79 , pp. 871-874
    • Brouillette, W.J.1    Brown, G.B.2    Delorey, T.M.3    Liang, G.4
  • 25
    • 0001666825 scopus 로고
    • The stereochemical basis of anticonvulsant drug action. I. The crystal and molecular structure of diphenylhydantoin, a noncentrosymmetric structure solved by centric symbolic addition
    • Camerman, A.; Camerman, N. The Stereochemical Basis of Anticonvulsant Drug Action. I. The Crystal and Molecular Structure of Diphenylhydantoin, a Noncentrosymmetric Structure Solved by Centric Symbolic Addition. Acta Crystallogr. 1971, B27, 2205-2211.
    • (1971) Acta Crystallogr. , vol.B27 , pp. 2205-2211
    • Camerman, A.1    Camerman, N.2
  • 26
    • 0041141210 scopus 로고
    • Synthesis of α-hydroxyamides via the cyanosilylation of aromatic ketones
    • Grunewald, G. L.; Brouillette, W. J.; Finney, J. Synthesis of α-Hydroxyamides via the Cyanosilylation of Aromatic Ketones. Tetrahedron Lett. 1980, 21, 1219-1220.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1219-1220
    • Grunewald, G.L.1    Brouillette, W.J.2    Finney, J.3
  • 29
    • 84982077292 scopus 로고
    • Polycyclische systeme mit heteroatomen
    • Huisgen, R.; Ugi, I. Polycyclische Systeme mit Heteroatomen. Liebigs Ann. Chem. 1957, 610, 57-66.
    • (1957) Liebigs Ann. Chem. , vol.610 , pp. 57-66
    • Huisgen, R.1    Ugi, I.2
  • 30
    • 0014876891 scopus 로고
    • Structure-activity correlations for anticonvulsant drugs
    • Lien, E. Structure-Activity Correlations for Anticonvulsant Drugs. J. Med. Chem. 1970, 13, 1189-1191.
    • (1970) J. Med. Chem. , vol.13 , pp. 1189-1191
    • Lien, E.1
  • 31
    • 0025167572 scopus 로고
    • Partition coefficients of three new anticonvulsants
    • Hernandez-Gallegos, Z.; Lehmann, P. A. F. Partition Coefficients of Three New Anticonvulsants. J. Pharm. Sci. 1990, 79, 1032-1033.
    • (1990) J. Pharm. Sci. , vol.79 , pp. 1032-1033
    • Hernandez-Gallegos, Z.1    Lehmann, P.A.F.2
  • 32
    • 0023691172 scopus 로고
    • Anticonvulsant activities of phenyl-substituted bicyclic 2,4-oxazolidinediones and monocyclic models. Comparison with binding to the neuronal voltage-dependent sodium channel
    • Brouillette, W. J.; Brown, G. B.; Delorey, T. M.; Shirali, S. S.; Grunewald, G. L. Anticonvulsant Activities of Phenyl-Substituted Bicyclic 2,4-Oxazolidinediones and Monocyclic Models. Comparison with Binding to the Neuronal Voltage-Dependent Sodium Channel. J. Med. Chem. 1988, 31, 2218-2221.
    • (1988) J. Med. Chem. , vol.31 , pp. 2218-2221
    • Brouillette, W.J.1    Brown, G.B.2    Delorey, T.M.3    Shirali, S.S.4    Grunewald, G.L.5
  • 33
    • 0023552075 scopus 로고
    • Physicochemical properties and X-ray structural studies of the trigonal polymorph of carbamazepine
    • Lowes, M. M. J.; Caira, M. R.; Lötter, A. P.; Van Der Watt, J. G. Physicochemical Properties and X-ray Structural Studies of the Trigonal Polymorph of Carbamazepine. J. Pharm. Sci. 1987, 76, 744-752.
    • (1987) J. Pharm. Sci. , vol.76 , pp. 744-752
    • Lowes, M.M.J.1    Caira, M.R.2    Lötter, A.P.3    Van Der Watt, J.G.4
  • 34
    • 0015503526 scopus 로고
    • Stereochemical basis of anticonvulsant drug action II. Molecular structure of diazepam
    • Camerman, A.; Camerman, N. Stereochemical Basis of Anticonvulsant Drug Action II. Molecular Structure of Diazepam. J. Am. Chem. Soc. 1972, 94, 268-272.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 268-272
    • Camerman, A.1    Camerman, N.2
  • 35
    • 0001248949 scopus 로고
    • The crystal structure of lidocaine hydrochloride monohydrate
    • Hanson, A. W.; Röhrl, M. The Crystal Structure of Lidocaine Hydrochloride Monohydrate. Acta Crystallogr. 1972, B28, 3567-3571.
    • (1972) Acta Crystallogr. , vol.B28 , pp. 3567-3571
    • Hanson, A.W.1    Röhrl, M.2
  • 36
    • 0024462231 scopus 로고
    • Evidence for a common site of action of lidocaine and carbamazepine in voltage-dependent sodium channels
    • Zimányi, I.; Weiss, S. R. B.; Lajtha, A.; Post, R. M.; Maarten, E. A. R. Evidence for a Common Site of Action of Lidocaine and Carbamazepine in Voltage-Dependent Sodium Channels. Eur. J. Pharmacol. 1989, 167, 419-422.
    • (1989) Eur. J. Pharmacol. , vol.167 , pp. 419-422
    • Zimányi, I.1    Weiss, S.R.B.2    Lajtha, A.3    Post, R.M.4    Maarten, E.A.R.5
  • 37
    • 0021288483 scopus 로고
    • 3H-batrachotoxin A 20-□-benzoate to sodium channels by local anesthetics
    • 3H-Batrachotoxin A 20-□-Benzoate to Sodium Channels by Local Anesthetics. Mol. Pharmacol. 1984, 25, 219-227.
    • (1984) Mol. Pharmacol. , vol.25 , pp. 219-227
    • Postma, S.W.1    Catterall, W.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.