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Volumn 77, Issue 1, 2011, Pages 75-85

QSAR Analysis for Some Diaryl-substituted Pyrazoles as CCR2 Inhibitors by GA-Stepwise MLR

Author keywords

CCR2 inhibitors; Genetic algorithm; Multivariate linear regression; Quantitative structure property relationship

Indexed keywords

CHEMOKINE RECEPTOR CCR2; PYRAZOLE;

EID: 78650120896     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2010.01053.x     Document Type: Article
Times cited : (26)

References (47)
  • 1
    • 0031838596 scopus 로고    scopus 로고
    • Chemokine receptors in the human brain and their relationship to HIV infection Anthony
    • Lavi E., Kolson D.L., Ulrich A.M., Fu L., GonzaAlez-Scarano F. (1998) Chemokine receptors in the human brain and their relationship to HIV infection Anthony. J Neurovirol;4:301-311.
    • (1998) J Neurovirol , vol.4 , pp. 301-311
    • Lavi, E.1    Kolson, D.L.2    Ulrich, A.M.3    Fu, L.4    GonzaAlez-Scarano, F.5
  • 2
    • 4744352502 scopus 로고    scopus 로고
    • Expression of CCR2 on monocytes and macrophages in chronically inflamed skin in atopic dermatitis and psoriasis
    • Vestergaard C., Just H., Nielsen J.B., Thestrup-Pedersen K., Deleuran M. (2004) Expression of CCR2 on monocytes and macrophages in chronically inflamed skin in atopic dermatitis and psoriasis. Acta Derm Venereol;84:353-358.
    • (2004) Acta Derm Venereol , vol.84 , pp. 353-358
    • Vestergaard, C.1    Just, H.2    Nielsen, J.B.3    Thestrup-Pedersen, K.4    Deleuran, M.5
  • 3
    • 0032509889 scopus 로고    scopus 로고
    • Chemokines-chemotactic cytokines that mediate inflammation
    • Luster A.D. (1998) Chemokines-chemotactic cytokines that mediate inflammation. N Engl J Med;338:436-445.
    • (1998) N Engl J Med , vol.338 , pp. 436-445
    • Luster, A.D.1
  • 4
    • 0032143524 scopus 로고    scopus 로고
    • Chemokines: understanding their role in T-lymphocyte biology
    • Ward S.G., Westwick J. (1998) Chemokines: understanding their role in T-lymphocyte biology. Biochem J;333:457-470.
    • (1998) Biochem J , vol.333 , pp. 457-470
    • Ward, S.G.1    Westwick, J.2
  • 6
    • 0033083950 scopus 로고    scopus 로고
    • Opportunities for novel therapeutic agents acting at chemokine receptors
    • Saunders J., Tarby C.M. (1999) Opportunities for novel therapeutic agents acting at chemokine receptors. Drug Discov Today;4:80-92.
    • (1999) Drug Discov Today , vol.4 , pp. 80-92
    • Saunders, J.1    Tarby, C.M.2
  • 8
    • 0028316908 scopus 로고
    • Molecular cloning and functional expression of two monocyte chemoattractant protein 1 receptors reveals alternative splicing of the carboxyl-terminal tails
    • Charo I.F., Myers S.J., Herman A., Franci C., Connolly A.J., Coughlin S.R. (1994) Molecular cloning and functional expression of two monocyte chemoattractant protein 1 receptors reveals alternative splicing of the carboxyl-terminal tails. Proc Natl Acad Sci USA;91:2752-2756.
    • (1994) Proc Natl Acad Sci USA , vol.91 , pp. 2752-2756
    • Charo, I.F.1    Myers, S.J.2    Herman, A.3    Franci, C.4    Connolly, A.J.5    Coughlin, S.R.6
  • 9
    • 0032773634 scopus 로고    scopus 로고
    • Monocyte chemoattractant protein-1
    • Gu L., Tseng S.C., Rollins B. (1999) Monocyte chemoattractant protein-1. Chem Immunol;72:7-29.
    • (1999) Chem Immunol , vol.72 , pp. 7-29
    • Gu, L.1    Tseng, S.C.2    Rollins, B.3
  • 10
    • 0030626161 scopus 로고    scopus 로고
    • Biological responses to C-C chemokines
    • Newton R.C., Vaddi K. (1997) Biological responses to C-C chemokines. Methods Enzymol;287:174-186.
    • (1997) Methods Enzymol , vol.287 , pp. 174-186
    • Newton, R.C.1    Vaddi, K.2
  • 11
    • 32144454172 scopus 로고    scopus 로고
    • The many roles of chemokines and chemokine receptors in inflammation
    • Charo I.F., Ransohoff R.M. (2006) The many roles of chemokines and chemokine receptors in inflammation. N Engl J Med;354:610-621.
    • (2006) N Engl J Med , vol.354 , pp. 610-621
    • Charo, I.F.1    Ransohoff, R.M.2
  • 12
    • 0032415886 scopus 로고    scopus 로고
    • Acute and relapsing experimental autoimmune encephalomyelitis are regulated by differential expression of the CC chemokines macrophage inflammatory protein-1á and monocyte chemotactic protein-1
    • Kennedy K.J., Strieter R.M., Kunkel S.L., Lukacs N.W., Karpus W.J. (1998) Acute and relapsing experimental autoimmune encephalomyelitis are regulated by differential expression of the CC chemokines macrophage inflammatory protein-1á and monocyte chemotactic protein-1. J Neuroimmunol;92:98-108.
    • (1998) J Neuroimmunol , vol.92 , pp. 98-108
    • Kennedy, K.J.1    Strieter, R.M.2    Kunkel, S.L.3    Lukacs, N.W.4    Karpus, W.J.5
  • 16
    • 34250209185 scopus 로고    scopus 로고
    • 3-Amino-1-alkyl-cyclopentane carboxamides as small molecule antagonists of the human and murine CC chemokine receptor 2h
    • Butora G., Jiao R., Parsons W.H., Vicario P.P., Jin H., Ayala J.M., Cascieri M.A., Yang L. (2007) 3-Amino-1-alkyl-cyclopentane carboxamides as small molecule antagonists of the human and murine CC chemokine receptor 2h. Bioorg Med Chem Lett;17:3636-3641.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 3636-3641
    • Butora, G.1    Jiao, R.2    Parsons, W.H.3    Vicario, P.P.4    Jin, H.5    Ayala, J.M.6    Cascieri, M.A.7    Yang, L.8
  • 17
    • 0346099273 scopus 로고    scopus 로고
    • N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor
    • Kettle J.G., Faull A.W., Barker A.J., Davies D.H., Stone M.A. (2004) N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor. Bioorg Med Chem Lett;14:405-408.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 405-408
    • Kettle, J.G.1    Faull, A.W.2    Barker, A.J.3    Davies, D.H.4    Stone, M.A.5
  • 18
    • 5344280480 scopus 로고    scopus 로고
    • Small molecule inhibitors of the CCR2b receptor. Part 1: discovery and optimization of homopiperazine derivatives
    • Imai M., Shiota T., Kataoka K., Tarby C.M., Moree W.J., Tsutsumi T., Sudo M. et al. (2004) Small molecule inhibitors of the CCR2b receptor. Part 1: discovery and optimization of homopiperazine derivatives. Bioorg Med Chem Lett;14:5407-5411.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 5407-5411
    • Imai, M.1    Shiota, T.2    Kataoka, K.3    Tarby, C.M.4    Moree, W.J.5    Tsutsumi, T.6    Sudo, M.7
  • 19
    • 5344256233 scopus 로고    scopus 로고
    • Small molecule antagonists of the CCR2b receptor. Part 2: discovery process and initial structure-activity relationships of diamine derivatives
    • Moree W.J., Kataoka K., Ramirez-Weinhouse M.M., Shiota T., Imai M., Sudo M., Tsutsumi T. et al. (2004) Small molecule antagonists of the CCR2b receptor. Part 2: discovery process and initial structure-activity relationships of diamine derivatives. Bioorg Med Chem Lett;14:5413-5416.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 5413-5416
    • Moree, W.J.1    Kataoka, K.2    Ramirez-Weinhouse, M.M.3    Shiota, T.4    Imai, M.5    Sudo, M.6    Tsutsumi, T.7
  • 20
    • 0035263818 scopus 로고    scopus 로고
    • Chem-Bioinformatics and QSAR: a review of QSAR lacking positive hydrophobic terms
    • Hansch C., Kurup A., Garg R., Gao H. (2001) Chem-Bioinformatics and QSAR: a review of QSAR lacking positive hydrophobic terms. Chem Rev;101:619-672.
    • (2001) Chem Rev , vol.101 , pp. 619-672
    • Hansch, C.1    Kurup, A.2    Garg, R.3    Gao, H.4
  • 21
    • 70349107717 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship studies on 2-amino-6-arylsulfonylbenzonitriles as human immunodeficiency viruses type 1 reverse transcriptase inhibitors using descriptors obtained from substituents and whole molecular structures
    • Hemmateenejad B., Sabet R., Fassihi A. (2009) Quantitative structure-activity relationship studies on 2-amino-6-arylsulfonylbenzonitriles as human immunodeficiency viruses type 1 reverse transcriptase inhibitors using descriptors obtained from substituents and whole molecular structures. Chem Biol Drug Des;74:405-415.
    • (2009) Chem Biol Drug Des , vol.74 , pp. 405-415
    • Hemmateenejad, B.1    Sabet, R.2    Fassihi, A.3
  • 22
    • 77956186611 scopus 로고    scopus 로고
    • QSAR study of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2 using LS-SVM and GRNN based on principal components
    • Shahlaei M., Sabet R., Ziari M.B., Moeinifard B., Fassihi A., Karbakhsh R. (2010) QSAR study of anthranilic acid sulfonamides as inhibitors of methionine aminopeptidase-2 using LS-SVM and GRNN based on principal components. Eur J Med Chem;45:4499-4508.
    • (2010) Eur J Med Chem , vol.45 , pp. 4499-4508
    • Shahlaei, M.1    Sabet, R.2    Ziari, M.B.3    Moeinifard, B.4    Fassihi, A.5    Karbakhsh, R.6
  • 23
    • 77349103400 scopus 로고    scopus 로고
    • Application of PC-ANN and PC-LS-SVM in QSAR of CCR1 antagonist compounds: a comparative study
    • Shahlaei M., Fassihi A., Saghaie L. (2010) Application of PC-ANN and PC-LS-SVM in QSAR of CCR1 antagonist compounds: a comparative study. Eur J Med Chem;45:1572-1582.
    • (2010) Eur J Med Chem , vol.45 , pp. 1572-1582
    • Shahlaei, M.1    Fassihi, A.2    Saghaie, L.3
  • 24
    • 38949111736 scopus 로고    scopus 로고
    • QSAR studies on CCR2 antagonists with chiral sensitive hologram descriptors
    • Nair P.C., Srikanth K., Sobhia M.E. (2008) QSAR studies on CCR2 antagonists with chiral sensitive hologram descriptors. Bioorg Med Chem Lett;18:1323-1330.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 1323-1330
    • Nair, P.C.1    Srikanth, K.2    Sobhia, M.E.3
  • 25
    • 38949111739 scopus 로고    scopus 로고
    • Probing the structural and topological requirements for CCR2 antagonism: holographic QSAR for indolopiperidine derivatives
    • Srikanth K., Nair P.C., Sobhia M.E. (2008) Probing the structural and topological requirements for CCR2 antagonism: holographic QSAR for indolopiperidine derivatives. Bioorg Med Chem Lett;18:41450-41456.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 41450-41456
    • Srikanth, K.1    Nair, P.C.2    Sobhia, M.E.3
  • 26
    • 54249157966 scopus 로고    scopus 로고
    • Fingerprint Directed Scaffold Hopping for Identification of CCR2 Antagonists
    • Nair P.C., Sobhia M.E. (2008) Fingerprint Directed Scaffold Hopping for Identification of CCR2 Antagonists. J Chem Inf Model;48:1891-1902.
    • (2008) J Chem Inf Model , vol.48 , pp. 1891-1902
    • Nair, P.C.1    Sobhia, M.E.2
  • 28
    • 78650158926 scopus 로고    scopus 로고
    • Milano Chemometrics and QSAR Group (). Dragon 2.1, available at .
    • Todeschini R. Milano Chemometrics and QSAR Group (2009). Dragon 2.1, available at
    • (2009)
    • Todeschini, R.1
  • 29
    • 0004315104 scopus 로고    scopus 로고
    • Handbook of Molecular Descriptors
    • Weinheim, Germany: Wiley-VCH.
    • Todeschini R., Consonni V. (2000) Handbook of Molecular Descriptors. Weinheim, Germany: Wiley-VCH.
    • (2000)
    • Todeschini, R.1    Consonni, V.2
  • 30
    • 1642380461 scopus 로고    scopus 로고
    • The Problem of Overfitting
    • Hawkins D.M. (2004) The Problem of Overfitting. J Chem Inf Comput Sci;44:1-12.
    • (2004) J Chem Inf Comput Sci , vol.44 , pp. 1-12
    • Hawkins, D.M.1
  • 31
    • 78650149306 scopus 로고    scopus 로고
    • Identification of a preferred set of molecular descriptors for compound classification based on principal component analysis
    • Xue L., Godden J., Gao H., Bajorath J. (1999) Identification of a preferred set of molecular descriptors for compound classification based on principal component analysis. J Chem Inf Comput Sci;3:9.
    • (1999) J Chem Inf Comput Sci , vol.3 , pp. 9
    • Xue, L.1    Godden, J.2    Gao, H.3    Bajorath, J.4
  • 32
    • 13044300880 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship modeling of dopamine D1 antagonists using comparative molecular field analysis, genetic algorithms-partial least-squares, and K nearest neighbor methods
    • Hoffman B., Cho S.J., Zheng W., Wyrick S., Nichols D.E., Mailman R.B., Tropsha A. (1999) Quantitative structure-activity relationship modeling of dopamine D1 antagonists using comparative molecular field analysis, genetic algorithms-partial least-squares, and K nearest neighbor methods. J Med Chem;42:3217-3226.
    • (1999) J Med Chem , vol.42 , pp. 3217-3226
    • Hoffman, B.1    Cho, S.J.2    Zheng, W.3    Wyrick, S.4    Nichols, D.E.5    Mailman, R.B.6    Tropsha, A.7
  • 33
    • 0000378338 scopus 로고    scopus 로고
    • Novel variable selection quantitative structure-property relationship approach based on the k-nearest-neighbor principle
    • Zheng W., Tropsha A. (2000) Novel variable selection quantitative structure-property relationship approach based on the k-nearest-neighbor principle. J Chem Inf Comput Sci;40:185-194.
    • (2000) J Chem Inf Comput Sci , vol.40 , pp. 185-194
    • Zheng, W.1    Tropsha, A.2
  • 34
    • 0003463297 scopus 로고
    • Adaption in natural and artificial systems
    • Ann Arbor, MI, USA: The University of Michigan Press.
    • Holland J.H. (1975) Adaption in natural and artificial systems. Ann Arbor, MI, USA: The University of Michigan Press.
    • (1975)
    • Holland, J.H.1
  • 35
    • 77954309516 scopus 로고    scopus 로고
    • Validated QSAR analysis of some diaryl substituted pyrazoles as CCR2 inhibitors by various linear and nonlinear multivariate chemometrics methods
    • Arkan E., Shahlaei M., Pourhossein A., Fakhri K., Fassihi A. (2010) Validated QSAR analysis of some diaryl substituted pyrazoles as CCR2 inhibitors by various linear and nonlinear multivariate chemometrics methods. Eur J Med Chem;45:3394-3406.
    • (2010) Eur J Med Chem , vol.45 , pp. 3394-3406
    • Arkan, E.1    Shahlaei, M.2    Pourhossein, A.3    Fakhri, K.4    Fassihi, A.5
  • 36
    • 0003868941 scopus 로고    scopus 로고
    • User friendly multivariate calibration
    • Chichester, UK: NIR Publications.
    • Naes T., Isaksson T., Fearn T., Davies T. (2002) User friendly multivariate calibration. Chichester, UK: NIR Publications.
    • (2002)
    • Naes, T.1    Isaksson, T.2    Fearn, T.3    Davies, T.4
  • 37
    • 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. (2003) The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb Sci;22:69-77.
    • (2003) QSAR Comb Sci , vol.22 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 38
    • 25444510806 scopus 로고    scopus 로고
    • Two- and three-way chemometrics methods applied for spectrophotometric determination of lorazepam in pharmaceutical formulations and biological fluids
    • Ghasemi J., Niazi A. (2005) Two- and three-way chemometrics methods applied for spectrophotometric determination of lorazepam in pharmaceutical formulations and biological fluids. Anal Chim Acta;533:169-177.
    • (2005) Anal Chim Acta , vol.533 , pp. 169-177
    • Ghasemi, J.1    Niazi, A.2
  • 39
    • 41949116226 scopus 로고    scopus 로고
    • On some aspects of variable selection for partial least squares regression models
    • Roy P., Roy K. (2008) On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci;27:302-313.
    • (2008) QSAR Comb Sci , vol.27 , pp. 302-313
    • Roy, P.1    Roy, K.2
  • 40
    • 11144354205 scopus 로고    scopus 로고
    • Application of predictive QSAR models to database mining: identification and experimental validation of novel anticonvulsant compounds
    • Shen M., Beguin C., Golbraikh A., Stables J., Kohn H., Tropsha A. (2009) Application of predictive QSAR models to database mining: identification and experimental validation of novel anticonvulsant compounds. J Med Chem;47:2356-2364.
    • (2009) J Med Chem , vol.47 , pp. 2356-2364
    • Shen, M.1    Beguin, C.2    Golbraikh, A.3    Stables, J.4    Kohn, H.5    Tropsha, A.6
  • 41
    • 84950461478 scopus 로고
    • Estimating the error rate of a prediction rule: improvement on cross-validation
    • Efron B. (1983) Estimating the error rate of a prediction rule: improvement on cross-validation. J Am Stat Assoc;78:316-331.
    • (1983) J Am Stat Assoc , vol.78 , pp. 316-331
    • Efron, B.1
  • 43
    • 0002656714 scopus 로고    scopus 로고
    • Selection of optimal regression models via cross-validation
    • Osten D.W. (1998) Selection of optimal regression models via cross-validation. J Chemom;2:39-48.
    • (1998) J Chemom , vol.2 , pp. 39-48
    • Osten, D.W.1
  • 44
    • 0002566234 scopus 로고
    • Constitutional and steric isomers of substituted cycloalkanes
    • Balaban A.T. (1978) Constitutional and steric isomers of substituted cycloalkanes. Croat Chem Acta;51:35-42.
    • (1978) Croat Chem Acta , vol.51 , pp. 35-42
    • Balaban, A.T.1
  • 45
    • 0030521035 scopus 로고
    • Reviews in Computational Chemistry
    • In: Lipkowitz K.B., Boyd D., eds. Weinheim, Germany: VCH
    • Arteca G.A. (1991) Molecular shape descriptors. In: Lipkowitz K.B., Boyd D. eds. Reviews in Computational Chemistry. Weinheim, Germany: VCH; p. 191-253.
    • (1991) Molecular shape descriptors , pp. 191-253
    • Arteca, G.A.1
  • 46
    • 0003397206 scopus 로고
    • Theory of Electric Polarization
    • Amsterdam, Netherlands: Elsevier
    • Bottcher C.J.F., Van Belle O.C., Bordewijk P., Rip A. (1973) Theory of Electric Polarization. Amsterdam, Netherlands: Elsevier; p. 378.
    • (1973) , pp. 378
    • Bottcher, C.J.F.1    Van Belle, O.C.2    Bordewijk, P.3    Rip, A.4


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