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Volumn 47, Issue 9, 2004, Pages 2356-2364

Application of Predictive QSAR Models to Database Mining: Identification and Experimental Validation of Novel Anticonvulsant Compounds

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTICONVULSIVE AGENT;

EID: 11144354205     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030584q     Document Type: Article
Times cited : (145)

References (41)
  • 1
    • 0028152905 scopus 로고
    • Cost of epilepsy in the United States: A model based on incidence and prognosis
    • Begley, C. E.; Annegers, J. F.; Lairson, D. R.; Reynolds, T. F.; Hauser, W. A. Cost of epilepsy in the United States: A model based on incidence and prognosis. Epilepsia 1994, 35, 1230-1243.
    • (1994) Epilepsia , vol.35 , pp. 1230-1243
    • Begley, C.E.1    Annegers, J.F.2    Lairson, D.R.3    Reynolds, T.F.4    Hauser, W.A.5
  • 2
    • 0025050694 scopus 로고    scopus 로고
    • Antiepileptic drugs: Pharmacological mechanisms and clinical efficacy with consideration of promising development stage compounds
    • Rogawski, M. A.; Porter, R. J. Antiepileptic drugs: Pharmacological mechanisms and clinical efficacy with consideration of promising development stage compounds. Pharmacol. Rev. 1997, 42, 223-286.
    • (1997) Pharmacol. Rev. , vol.42 , pp. 223-286
    • Rogawski, M.A.1    Porter, R.J.2
  • 4
    • 0021887675 scopus 로고
    • Comparison of carbamazepine, phenobarbital, phenytoin, and primidone in partial and secondarily genealized tonic-clonic seizures
    • Mattson, R. H.; Cramer, J. A.; Collins, J. F.; Smith, D. B. Comparison of carbamazepine, phenobarbital, phenytoin, and primidone in partial and secondarily genealized tonic-clonic seizures. New Eng. J. Med. 1985, 313, 145-151.
    • (1985) New Eng. J. Med. , vol.313 , pp. 145-151
    • Mattson, R.H.1    Cramer, J.A.2    Collins, J.F.3    Smith, D.B.4
  • 5
    • 0026014156 scopus 로고
    • A rational guide to monitoring in patients receiving anticonvulsants
    • Pellock, J. M.; Willmore, L. J. A rational guide to monitoring in patients receiving anticonvulsants. Neurology 1991, 41, 961-964.
    • (1991) Neurology , vol.41 , pp. 961-964
    • Pellock, J.M.1    Willmore, L.J.2
  • 6
    • 0025238774 scopus 로고
    • Preparation and anticonvulsant activity of a series of functionalized α-aromatic and α-heteroaromatic amino acids
    • Kohn, H.; Sawhney, K. N.; LeGall, P.; Conley, J. D.; Robertson, D. W.; Leander, J. D. Preparation and anticonvulsant activity of a series of functionalized α-aromatic and α-heteroaromatic amino acids. J. Med. Chem. 1990, 33, 919-926.
    • (1990) J. Med. Chem. , vol.33 , pp. 919-926
    • Kohn, H.1    Sawhney, K.N.2    LeGall, P.3    Conley, J.D.4    Robertson, D.W.5    Leander, J.D.6
  • 7
    • 0027443545 scopus 로고
    • Synthesis and anticonvulsant activities of α-heteroaromatic-α -acetamido-N-benzylacetamide derivatives
    • Kohn, H.; Sawhney, K. H.; Bardel, P.; Robertson, D. W.; Leander, J. D. Synthesis and anticonvulsant activities of α-heteroaromatic-α -acetamido-N-benzylacetamide derivatives. J. Med. Chem. 1993, 36, 3350-3360.
    • (1993) J. Med. Chem. , vol.36 , pp. 3350-3360
    • Kohn, H.1    Sawhney, K.H.2    Bardel, P.3    Robertson, D.W.4    Leander, J.D.5
  • 8
    • 0029898015 scopus 로고    scopus 로고
    • Synthesis and anticonvulsant activities of N-benzyl-2-acetamidopropionamide derivatives
    • Choi, D.; Stables, J. P.; Kohn, H. Synthesis and anticonvulsant activities of N-benzyl-2-acetamidopropionamide derivatives. J. Med. Chem. 1996, 39, 1907-1916.
    • (1996) J. Med. Chem. , vol.39 , pp. 1907-1916
    • Choi, D.1    Stables, J.P.2    Kohn, H.3
  • 10
    • 0002544304 scopus 로고
    • Levy, R. H., Driefuss, F. E., Mattson, R. H., Meldrum, B. S., Perry, J. K., Eds.; Raven Press: New York
    • Swinyard, E. A.; Woodhead, J. H.; White, H. S.; Franklin, M. R. In Antiepileptic Drugs, 3rd Edn.; Levy, R. H., Driefuss, F. E., Mattson, R. H., Meldrum, B. S., Perry, J. K., Eds.; Raven Press: New York, 1989; pp 85-102.
    • (1989) Antiepileptic Drugs, 3rd Edn. , pp. 85-102
    • Swinyard, E.A.1    Woodhead, J.H.2    White, H.S.3    Franklin, M.R.4
  • 12
    • 0037142302 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship analysis of functionalized amino acid anticonvulsant agents using k nearest neighbor and simulated annealing PLS methods
    • Shen, M.; LeTiran, A.; Xiao, Y.; Golbraikh, A.; Kohn, H.; Tropsha, A. Quantitative structure-activity relationship analysis of functionalized amino acid anticonvulsant agents using k nearest neighbor and simulated annealing PLS methods. J. Med. Chem. 2002, 45, 2811-2823.
    • (2002) J. Med. Chem. , vol.45 , pp. 2811-2823
    • Shen, M.1    LeTiran, A.2    Xiao, Y.3    Golbraikh, A.4    Kohn, H.5    Tropsha, A.6
  • 13
    • 0141882047 scopus 로고    scopus 로고
    • History and evolution of the pharmacophore concept in computer-aided drug design
    • Güner, O. F. History and evolution of the pharmacophore concept in computer-aided drug design. Curr. Top. Med. Chem. 2002, 2, 1321-1332.
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 1321-1332
    • Güner, O.F.1
  • 14
    • 0034934377 scopus 로고    scopus 로고
    • Pharmacophore modeling and three-dimensional database searching for drug design using Catalyst
    • Kurogi, Y.; Güner, O. F. Pharmacophore modeling and three-dimensional database searching for drug design using Catalyst. Curr. Med. Chem. 2001, 8, 1035-1055.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1035-1055
    • Kurogi, Y.1    Güner, O.F.2
  • 15
    • 0026642983 scopus 로고
    • 3D database searching in drug design
    • Martin, Y. C. 3D database searching in drug design. J. Med. Chem. 1992, 35, 2145-2154.
    • (1992) J. Med. Chem. , vol.35 , pp. 2145-2154
    • Martin, Y.C.1
  • 16
    • 0035003411 scopus 로고    scopus 로고
    • Identification of the descriptor pharmacophores using variable selection QSAR: Applications to database mining
    • Tropsha, A.; Zheng, W. Identification of the descriptor pharmacophores using variable selection QSAR: Applications to database mining. Curr. Pharm. Design 2001, 7, 599-612.
    • (2001) Curr. Pharm. Design , vol.7 , pp. 599-612
    • Tropsha, A.1    Zheng, W.2
  • 17
    • 0040790525 scopus 로고    scopus 로고
    • "New Tricks for an Old Dog": Development and application of novel QSAR methods for rational design of combinatorial chemical libraries and database mining
    • Parrill, A. L., Reddy, M. R., Eds.; ACS Symposium Series 719; American Chemical Society: Washington, DC
    • Tropsha, A.; Cho, S. J.; Zheng, W. "New Tricks For an Old Dog": Development and application of novel QSAR methods for rational design of combinatorial chemical libraries and database mining. In Rational Drug Design: Novel Methodology and Practical Applications; Parrill, A. L., Reddy, M. R., Eds.; ACS Symposium Series 719; American Chemical Society: Washington, DC, 1999; pp 198-211.
    • (1999) Rational Drug Design: Novel Methodology and Practical Applications , pp. 198-211
    • Tropsha, A.1    Cho, S.J.2    Zheng, W.3
  • 18
    • 0008968778 scopus 로고    scopus 로고
    • Rational combinatorial library design and database mining using inverse QSAR approach
    • Ghose, A. K., Viswanadhan, V. N., Eds.; Marcel Dekker, Inc., New York; Chapter 12
    • Tropsha, A. Rational combinatorial library design and database mining using inverse QSAR approach. In Combinatorial Library Design and Evaluation for Drug Discovery: Principles, Methods, Software Tools and Applications. Ghose, A. K., Viswanadhan, V. N., Eds.; Marcel Dekker, Inc., New York, 2001; Chapter 12, pp 363-378.
    • (2001) Combinatorial Library Design and Evaluation for Drug Discovery: Principles, Methods, Software Tools and Applications , pp. 363-378
    • Tropsha, A.1
  • 19
    • 0038724207 scopus 로고    scopus 로고
    • The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models
    • Tropsha, A.; Gramatica, P.; Gombar, V. K. The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models. Quant. Struct. Act. Relat. Comb. Sci. 2003, 22, 69-77.
    • (2003) Quant. Struct. Act. Relat. Comb. Sci. , vol.22 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 21
    • 1842663801 scopus 로고    scopus 로고
    • http://www.maybridge.com.
  • 22
    • 1842764348 scopus 로고    scopus 로고
    • http://dtp.nci.nih.gov/docs/3d_database/structural_information/ smiles_strings.html.
  • 23
    • 0004307893 scopus 로고    scopus 로고
    • Hall Associates Consulting: Quincy, MA
    • MolConn-Z, version 3.5; Hall Associates Consulting: Quincy, MA.
    • MolConn-Z, Version 3.5
  • 24
    • 13044300880 scopus 로고    scopus 로고
    • QSAR modeling of dopamine D1 agonists using comparative molecular field analysis, genetic algorithms-partial least squares, and K nearest neighbor methods
    • Hoffman, B. T.; Cho, S. J.; Zheng, W.; Wyrick, S.; Nichols, D. E.; Mailman, R. B.; Tropsha, A. QSAR modeling of dopamine D1 agonists using comparative molecular field analysis, genetic algorithms-partial least squares, and K nearest neighbor methods. J. Med. Chem. 1999, 42, 3217-3226.
    • (1999) J. Med. Chem. , vol.42 , pp. 3217-3226
    • Hoffman, B.T.1    Cho, S.J.2    Zheng, W.3    Wyrick, S.4    Nichols, D.E.5    Mailman, R.B.6    Tropsha, A.7
  • 25
    • 0032012086 scopus 로고    scopus 로고
    • Rational combinatorial library design. 2. Rational design of targeted combinatorial peptide libraries using chemical similarity probe and the inverse QSAR approaches
    • Cho, S. J.; Zheng, W.; Tropsha, A. Rational combinatorial library design. 2. Rational design of targeted combinatorial peptide libraries using chemical similarity probe and the inverse QSAR approaches. J. Chem. Inf. Comput. Sci. 1998, 38, 259-268.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 259-268
    • Cho, S.J.1    Zheng, W.2    Tropsha, A.3
  • 26
    • 0000378338 scopus 로고    scopus 로고
    • A novel variable selection QSAR approach based on the K-nearest neighbor principle
    • Zheng, W.; Tropsha, A. A novel variable selection QSAR approach based on the K-nearest neighbor principle. J. Chem. Inf. Comput. Sci. 2000, 40, 185-194.
    • (2000) J. Chem. Inf. Comput. Sci. , vol.40 , pp. 185-194
    • Zheng, W.1    Tropsha, A.2
  • 27
    • 0036589313 scopus 로고    scopus 로고
    • Predictive QSAR modeling based on rational division of experimental datasets into diverse training and test sets
    • Golbraikh, A.; Tropsha, A. Predictive QSAR modeling based on rational division of experimental datasets into diverse training and test sets. J. Comput. Aid. Mol. Des. 2002, 16, 357-369.
    • (2002) J. Comput. Aid. Mol. Des. , vol.16 , pp. 357-369
    • Golbraikh, A.1    Tropsha, A.2
  • 28
    • 0034841551 scopus 로고    scopus 로고
    • Functionalized amino acid anticonvulsants: Synthesis and pharmacological evaluation of conformationally restricted analogues
    • LeTiran, A.; Stables, J. P.; Kohn, H. Functionalized amino acid anticonvulsants: Synthesis and pharmacological evaluation of conformationally restricted analogues. Bioorg. Med. Chem. 2001, 9, 2693-2708.
    • (2001) Bioorg. Med. Chem. , vol.9 , pp. 2693-2708
    • LeTiran, A.1    Stables, J.P.2    Kohn, H.3
  • 29
    • 0031941914 scopus 로고    scopus 로고
    • N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants
    • Geurts, M.; Poupaert, J. H.; Scriba, G. K. E.; Lambert, D. M. N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants. J. Med. Chem. 1998, 41, 24-30.
    • (1998) J. Med. Chem. , vol.41 , pp. 24-30
    • Geurts, M.1    Poupaert, J.H.2    Scriba, G.K.E.3    Lambert, D.M.4
  • 32
    • 0022647189 scopus 로고
    • Pharmcokinetics of local anesthetics
    • Tucher, G. T. Pharmcokinetics of local anesthetics. Brit. J. Anaesth. 1986, 58, 717-731.
    • (1986) Brit. J. Anaesth. , vol.58 , pp. 717-731
    • Tucher, G.T.1
  • 34
    • 0028900559 scopus 로고
    • CYP3A4 and CYP2A6 activities marked by the metabolism of lignocaine and coumarin in patients with liver and kidney diseases and epileptic patients
    • Sotaniemi, E. A.; Rautio, A.; Backstrom, M.; Arvela, P.; Pelkonen, O. CYP3A4 and CYP2A6 activities marked by the metabolism of lignocaine and coumarin in patients with liver and kidney diseases and epileptic patients. Br. J. Clin. Pharmacol. 1995, 39, 71-76.
    • (1995) Br. J. Clin. Pharmacol. , vol.39 , pp. 71-76
    • Sotaniemi, E.A.1    Rautio, A.2    Backstrom, M.3    Arvela, P.4    Pelkonen, O.5
  • 35
    • 0021999826 scopus 로고
    • Effect of structural modification of the hydantoin ring on anticonvulsant activity
    • Cortes, S.; Liao, Z-K.; Watson, D.; Kohn, H. Effect of structural modification of the hydantoin ring on anticonvulsant activity. J. Med. Chem. 1985, 28, 601-606.
    • (1985) J. Med. Chem. , vol.28 , pp. 601-606
    • Cortes, S.1    Liao, Z.-K.2    Watson, D.3    Kohn, H.4
  • 36
    • 0035200133 scopus 로고    scopus 로고
    • Progress report on new antiepileptic drugs: A summary of the Fifth Eilat Conference (EILAT V)
    • Bialer, M.; Johannessen, S.; Kupferberg, H.; Levy, R.; Loiseau, P.; Perucca, E. Progress report on new antiepileptic drugs: A summary of the Fifth Eilat Conference (EILAT V). Epilepsy Res. 2001, 43, 11-58.
    • (2001) Epilepsy Res. , vol.43 , pp. 11-58
    • Bialer, M.1    Johannessen, S.2    Kupferberg, H.3    Levy, R.4    Loiseau, P.5    Perucca, E.6
  • 38
    • 0001284386 scopus 로고
    • Gold(I)-catalyzed asymmetric aldol reaction of N-methoxy-N-methyl-α -isocyano-acetamide (α-isocyano weinreb amide). An efficient synthesis of optically active β-hydroxy α-amino aldehydes and ketones
    • Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. Gold(I)-catalyzed asymmetric aldol reaction of N-methoxy-N-methyl-α-isocyano-acetamide (α-isocyano weinreb amide). An efficient synthesis of optically active β-hydroxy α-amino aldehydes and ketones. J. Org. Chem. 1995, 60, 1727-1732.
    • (1995) J. Org. Chem. , vol.60 , pp. 1727-1732
    • Sawamura, M.1    Nakayama, Y.2    Kato, T.3    Ito, Y.4
  • 39
    • 0015868812 scopus 로고
    • In vivo metabolite condensations. Formation of N1-ethyl-2-methyl-N3-(2,6-dimethylphenyl)-4-imidazolidinone from the reaction of a metabolite of alcohol with a metabolite of lidocaine
    • Nelson, S. D.; Breck, G. D.; Trager, W. F. In vivo metabolite condensations. Formation of N1-ethyl-2-methyl-N3-(2,6-dimethylphenyl)-4-imidazolidinone from the reaction of a metabolite of alcohol with a metabolite of lidocaine. J. Med. Chem. 1973, 16, 1106-1112.
    • (1973) J. Med. Chem. , vol.16 , pp. 1106-1112
    • Nelson, S.D.1    Breck, G.D.2    Trager, W.F.3
  • 40
    • 0025615325 scopus 로고
    • Saturated heterocycles, Part 172. Synthesis of 2,6-disubstituted-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Derivatives
    • Lazar, J.; Bernath, G. Saturated heterocycles, Part 172. Synthesis of 2,6-disubstituted-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine Derivatives. J. Heterocycl. Chem. 1990, 27, 1885-1892.
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 1885-1892
    • Lazar, J.1    Bernath, G.2


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