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Volumn 72, Issue 5, 2008, Pages 360-369

Docking and quantitative structure-activity relationship studies for the bisphenylbenzimidazole family of non-nucleoside inhibitors of HIV-1 reverse transcriptase

Author keywords

Bisphenylbenzimidazole derivatives; Docking; Non nucleoside HIV 1 reverse transcriptase inhibitors; Quantitative structure activity relationship; Radial distribution function descriptors

Indexed keywords

BENZIMIDAZOLE DERIVATIVE; BISPHENYLBENZIMIDAZOLE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 54249140977     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00716.x     Document Type: Article
Times cited : (31)

References (47)
  • 1
    • 12144265244 scopus 로고    scopus 로고
    • Non-nucleoside reverse transcriptase inhibitors (NNRTIs): Past, present, and future
    • De Clercq E. (2004) Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. Chem Biodivers 1 : 44 64.
    • (2004) Chem Biodivers , vol.1 , pp. 44-64
    • De Clercq, E.1
  • 3
    • 0029645409 scopus 로고
    • The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: Lessons for inhibitor design
    • Ren J., Esnouf R., Hopkins A., Ross C., Jones Y., Stammers D., Stuart D (1995) The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: lessons for inhibitor design. Structure 3 : 915 926.
    • (1995) Structure , vol.3 , pp. 915-926
    • Ren, J.1    Esnouf, R.2    Hopkins, A.3    Ross, C.4    Jones, Y.5    Stammers, D.6    Stuart, D.7
  • 4
    • 4544265135 scopus 로고    scopus 로고
    • Conformational changes in HIV-1 reverse transcriptase induced by nonnucleoside reverse transcriptase inhibitor binding
    • Sluis-Cremer N., Temiz N.A., Bahar I. (2004) Conformational changes in HIV-1 reverse transcriptase induced by nonnucleoside reverse transcriptase inhibitor binding. Curr HIV Res 2 : 323 332.
    • (2004) Curr HIV Res , vol.2 , pp. 323-332
    • Sluis-Cremer, N.1    Temiz, N.A.2    Bahar, I.3
  • 5
    • 0030057371 scopus 로고    scopus 로고
    • Anti-HIV agents. IV. Synthesis and in vitro anti-HIV activity of novel 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A., Grasso S., Molica C., Monforte A.M., Monforte P., Zappala M., Scopelliti R. (1996) Anti-HIV agents. IV. Synthesis and in vitro anti-HIV activity of novel 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazoles. Farmaco 51 : 279 282.
    • (1996) Farmaco , vol.51 , pp. 279-282
    • Chimirri, A.1    Grasso, S.2    Molica, C.3    Monforte, A.M.4    Monforte, P.5    Zappala, M.6    Scopelliti, R.7
  • 6
    • 0025812546 scopus 로고
    • Anti-HIV agents II. Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A., Grasso S., Monforte A.M., Monforte P., Zappala M. (1991) Anti-HIV agents II. Synthesis and in vitro anti-HIV activity of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. Farmaco 46 : 925 933.
    • (1991) Farmaco , vol.46 , pp. 925-933
    • Chimirri, A.1    Grasso, S.2    Monforte, A.M.3    Monforte, P.4    Zappala, M.5
  • 7
    • 0026324187 scopus 로고
    • Anti-HIV agents I. Synthesis and anti-HIV evaluation of novel 1H,3H-thiazolo[3,4-a]benzimidazoles
    • Chimirri A., Grasso S., Monforte A.M., Monforte P., Zappala M. (1991) Anti-HIV agents I. Synthesis and anti-HIV evaluation of novel 1H,3H-thiazolo[3,4-a]benzimidazoles. Farmaco 46 : 817 823.
    • (1991) Farmaco , vol.46 , pp. 817-823
    • Chimirri, A.1    Grasso, S.2    Monforte, A.M.3    Monforte, P.4    Zappala, M.5
  • 8
    • 0034797941 scopus 로고    scopus 로고
    • Synthesis, biological activity, pharmacokinetic properties and molecular modelling studies of novel 1H,3H-oxazolo[3,4-a]benzimidazoles: Non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Chimirri A., Monforte P., Rao A., Zappala M., Monforte A.M., De Sarro G., Pannecouque C., Witvrouw M., Balzarini J., De Clercq E. (2001) Synthesis, biological activity, pharmacokinetic properties and molecular modelling studies of novel 1H,3H-oxazolo[3,4-a]benzimidazoles: non-nucleoside HIV-1 reverse transcriptase inhibitors. Antivir Chem Chemother 12 : 169 174.
    • (2001) Antivir Chem Chemother , vol.12 , pp. 169-174
    • Chimirri, A.1    Monforte, P.2    Rao, A.3    Zappala, M.4    Monforte, A.M.5    De Sarro, G.6    Pannecouque, C.7    Witvrouw, M.8    Balzarini, J.9    De Clercq, E.10
  • 9
    • 1842866611 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of 1-(2,6-difluorophenyl)-1H,3H- thiazolo[3,4-a]benzimidazole structurally-related 1,2-substituted benzimidazoles
    • Rao A., Chimirri A., De Clercq E., Monforte A.M., Monforte P., Pannecouque C., Zappala M. (2002) Synthesis and anti-HIV activity of 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole structurally-related 1,2-substituted benzimidazoles. Farmaco 57 : 819 823.
    • (2002) Farmaco , vol.57 , pp. 819-823
    • Rao, A.1    Chimirri, A.2    De Clercq, E.3    Monforte, A.M.4    Monforte, P.5    Pannecouque, C.6    Zappala, M.7
  • 10
    • 0031463691 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-aryl-substituted benzimidazoles
    • Roth T., Morningstar M.L., Boyer P.L., Hughes S.H., Buckheit R.W. Jr., Michejda C.J. (1997) Synthesis and biological activity of novel nonnucleoside inhibitors of HIV-1 reverse transcriptase. 2-aryl-substituted benzimidazoles. J Med Chem 40 : 4199 4207.
    • (1997) J Med Chem , vol.40 , pp. 4199-4207
    • Roth, T.1    Morningstar, M.L.2    Boyer, P.L.3    Hughes, S.H.4    Buckheit Jr., R.W.5    Michejda, C.J.6
  • 11
    • 0033491040 scopus 로고    scopus 로고
    • Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNIs)
    • Barreca M.L., Carotti A., Carrieri A., Chimirri A., Monforte A.M., Calace M.P., Rao A. (1999) Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNIs). Bioorg Med Chem 7 : 2283 2292.
    • (1999) Bioorg Med Chem , vol.7 , pp. 2283-2292
    • Barreca, M.L.1    Carotti, A.2    Carrieri, A.3    Chimirri, A.4    Monforte, A.M.5    Calace, M.P.6    Rao, A.7
  • 14
    • 33646509695 scopus 로고    scopus 로고
    • Developing novel nonnucleoside HIV-1 reverse transcriptase inhibitors: Beyond the butterfly
    • Basavapathruni A., Anderson K.S. (2006) Developing novel nonnucleoside HIV-1 reverse transcriptase inhibitors: beyond the butterfly. Curr Pharm Des 12 : 1857 1865.
    • (2006) Curr Pharm des , vol.12 , pp. 1857-1865
    • Basavapathruni, A.1    Anderson, K.S.2
  • 15
    • 1042279567 scopus 로고    scopus 로고
    • A pharmacophore docking algorithm and its application to the cross-docking of 18 HIV-NNRTI's in their binding pockets
    • Daeyaert F., de Jonge M., Heeres J., Koymans L., Lewi P., Vinkers M.H., Janssen P.A. (2004) A pharmacophore docking algorithm and its application to the cross-docking of 18 HIV-NNRTI's in their binding pockets. Proteins 54 : 526 533.
    • (2004) Proteins , vol.54 , pp. 526-533
    • Daeyaert, F.1    De Jonge, M.2    Heeres, J.3    Koymans, L.4    Lewi, P.5    Vinkers, M.H.6    Janssen, P.A.7
  • 16
    • 9744258219 scopus 로고    scopus 로고
    • Crystallography and the design of anti-AIDS drugs: Conformational flexibility and positional adaptability are important in the design of non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Das K., Lewi P.J., Hughes S.H., Arnold E. (2005) Crystallography and the design of anti-AIDS drugs: conformational flexibility and positional adaptability are important in the design of non-nucleoside HIV-1 reverse transcriptase inhibitors. Prog Biophys Mol Biol 88 : 209 231.
    • (2005) Prog Biophys Mol Biol , vol.88 , pp. 209-231
    • Das, K.1    Lewi, P.J.2    Hughes, S.H.3    Arnold, E.4
  • 17
    • 18244373421 scopus 로고    scopus 로고
    • Common binding mode for structurally and chemically diverse non-nucleosidic HIV-1RT inhibitors
    • Yadav A., Kumar Singh S. (2005) Common binding mode for structurally and chemically diverse non-nucleosidic HIV-1RT inhibitors. J Mol Struct (Theochem) 723 : 205 209.
    • (2005) J Mol Struct (Theochem) , vol.723 , pp. 205-209
    • Yadav, A.1    Kumar Singh, S.2
  • 20
    • 0033628605 scopus 로고    scopus 로고
    • Use of artificial neural networks in a QSAR study of anti-HIV activity for a large group of HEPT derivatives
    • Jalali-Heravi M., Parastar F. (2000) Use of artificial neural networks in a QSAR study of anti-HIV activity for a large group of HEPT derivatives. J Chem Inf Comput Sci 40 : 147 154.
    • (2000) J Chem Inf Comput Sci , vol.40 , pp. 147-154
    • Jalali-Heravi, M.1    Parastar, F.2
  • 21
    • 0032741707 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships and comparative molecular field analysis of TIBO derivatised HIV-1 reverse transcriptase inhibitors
    • Hannongbua S., Pungpo P., Limtrakul J., Wolschann P. (1999) Quantitative structure-activity relationships and comparative molecular field analysis of TIBO derivatised HIV-1 reverse transcriptase inhibitors J Comput Aided Mol Des 13 : 563 577.
    • (1999) J Comput Aided Mol des , vol.13 , pp. 563-577
    • Hannongbua, S.1    Pungpo, P.2    Limtrakul, J.3    Wolschann, P.4
  • 23
    • 4344677342 scopus 로고    scopus 로고
    • QSAR Modeling of anti-HIV activities of alkenyldiarylmethanes using topological and physicochemical descriptors
    • Leonard J.T., Roy K. (2003) QSAR Modeling of anti-HIV activities of alkenyldiarylmethanes using topological and physicochemical descriptors. Drug Des Discov 18 : 165 180.
    • (2003) Drug des Discov , vol.18 , pp. 165-180
    • Leonard, J.T.1    Roy, K.2
  • 24
    • 37849187619 scopus 로고    scopus 로고
    • Molecular docking studies on 4-thiazolidinones as HIV-1 RT inhibitors
    • Rawal R.K., Kumar A., Siddiqi M.I., Katti S.B. (2007) Molecular docking studies on 4-thiazolidinones as HIV-1 RT inhibitors. J Mol Model 13 : 155 161.
    • (2007) J Mol Model , vol.13 , pp. 155-161
    • Rawal, R.K.1    Kumar, A.2    Siddiqi, M.I.3    Katti, S.B.4
  • 25
    • 12144279076 scopus 로고    scopus 로고
    • Docking and 3-D QSAR studies on indolyl aryl sulfones. Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active n-(2-hydroxyethyl)carboxamide and n-(2-hydroxyethyl) carbohydrazide derivatives
    • Ragno R., Artico M., De Martino G., La Regina G., Coluccia A., Di Pasquali A., Silvestri R. (2005) Docking and 3-D QSAR studies on indolyl aryl sulfones. Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active n-(2-hydroxyethyl) carboxamide and n-(2-hydroxyethyl)carbohydrazide derivatives. J Med Chem 48 : 213 223.
    • (2005) J Med Chem , vol.48 , pp. 213-223
    • Ragno, R.1    Artico, M.2    De Martino, G.3    La Regina, G.4    Coluccia, A.5    Di Pasquali, A.6    Silvestri, R.7
  • 26
    • 26044447233 scopus 로고    scopus 로고
    • Quantitative structure-activity relationship analysis of pyridinone HIV-1 reverse transcriptase inhibitors using the k nearest neighbor method and QSAR-based database mining
    • Medina-Franco J.L., Golbraikh A., Oloff S., Castillo R., Tropsha A. (2005) Quantitative structure-activity relationship analysis of pyridinone HIV-1 reverse transcriptase inhibitors using the k nearest neighbor method and QSAR-based database mining. J Comput Aided Mol Des 19 : 229 242.
    • (2005) J Comput Aided Mol des , vol.19 , pp. 229-242
    • Medina-Franco, J.L.1    Golbraikh, A.2    Oloff, S.3    Castillo, R.4    Tropsha, A.5
  • 29
    • 5544242529 scopus 로고    scopus 로고
    • MMFF VI. MMFF94s option for energy minimization studies
    • Halgren T.A. (1999) MMFF VI. MMFF94s option for energy minimization studies. J Comp Chem 20 : 720 729.
    • (1999) J Comp Chem , vol.20 , pp. 720-729
    • Halgren, T.A.1
  • 30
    • 0041781898 scopus 로고    scopus 로고
    • Detailed analysis of grid-based molecular docking: A case study of CDOCKER - A CHARMm-based MD docking algorithm
    • Wu G., Robertson D.H., Brooks C.L. III., Vieth M. (2003) Detailed analysis of grid-based molecular docking: A case study of CDOCKER - a CHARMm-based MD docking algorithm. J Comp Chem 24 : 1549 1562.
    • (2003) J Comp Chem , vol.24 , pp. 1549-1562
    • Wu, G.1    Robertson, D.H.2    Brooks Iii., C.L.3    Vieth, M.4
  • 31
    • 0034632804 scopus 로고    scopus 로고
    • DoMCoSAR: A novel approach for establishing the docking mode that is consistent with the structure-activity relationship. Application to HIV-1 protease inhibitors and VEGF receptor tyrosine kinase inhibitors
    • Vieth M., Cummins D.J. (2000) DoMCoSAR: a novel approach for establishing the docking mode that is consistent with the structure-activity relationship. Application to HIV-1 protease inhibitors and VEGF receptor tyrosine kinase inhibitors. J Med Chem 43 : 3020 3032.
    • (2000) J Med Chem , vol.43 , pp. 3020-3032
    • Vieth, M.1    Cummins, D.J.2
  • 34
    • 0028454828 scopus 로고
    • The development of a simple empirical scoring function to estimate the binding constant for a protein ligand complex of known 3-dimensional structure
    • Bohm H.J. (1994) The development of a simple empirical scoring function to estimate the binding constant for a protein ligand complex of known 3-dimensional structure. J Comput Aided Mol Des 8 : 243 256.
    • (1994) J Comput Aided Mol des , vol.8 , pp. 243-256
    • Bohm, H.J.1
  • 35
    • 0032112137 scopus 로고    scopus 로고
    • Prediction of binding constants of protein ligands: A fast method for the prioritization of hits obtained from de novo design or 3D database search programs
    • Bohm H.J. (1998) Prediction of binding constants of protein ligands: a fast method for the prioritization of hits obtained from de novo design or 3D database search programs. J Comput Aided Mol Des 12 : 309 323.
    • (1998) J Comput Aided Mol des , vol.12 , pp. 309-323
    • Bohm, H.J.1
  • 36
    • 0035498337 scopus 로고    scopus 로고
    • QSAR and k-nearest neighbor classification analysis of selective cyclooxygenase-2 inhibitors using topologically-based numerical descriptors
    • Kauffman G.W., Jurs P.C (2001) QSAR and k-nearest neighbor classification analysis of selective cyclooxygenase-2 inhibitors using topologically-based numerical descriptors. J Chem Inf Comput Sci 41 : 1553 1560.
    • (2001) J Chem Inf Comput Sci , vol.41 , pp. 1553-1560
    • Kauffman, G.W.1    Jurs, P.C.2
  • 39
    • 27744456972 scopus 로고    scopus 로고
    • Modeling of farnesyltransferase inhibition by some thiol and non-thiol peptidomimetic inhibitors using genetic neural networks and RDF approaches
    • González M.P., Caballero J., Tundidor-Camba A., Helguera A.M., Fernández M. (2006) Modeling of farnesyltransferase inhibition by some thiol and non-thiol peptidomimetic inhibitors using genetic neural networks and RDF approaches. Bioorg Med Chem 14 : 200 213.
    • (2006) Bioorg Med Chem , vol.14 , pp. 200-213
    • González, M.P.1    Caballero, J.2    Tundidor-Camba, A.3    Helguera, A.M.4    Fernández, M.5
  • 40
    • 11844300315 scopus 로고    scopus 로고
    • A radial distribution function approach to predict A(2B) agonist effect of adenosine analogues
    • González M.P., Teran C., Fall Y., Teijeira M., Besada P. (2005) A radial distribution function approach to predict A(2B) agonist effect of adenosine analogues Bioorg Med Chem 13 : 601 608.
    • (2005) Bioorg Med Chem , vol.13 , pp. 601-608
    • González, M.P.1    Teran, C.2    Fall, Y.3    Teijeira, M.4    Besada, P.5
  • 41
    • 33749266312 scopus 로고    scopus 로고
    • A radial-distribution-function approach for predicting rodent carcinogenicity
    • Helguera A.M., Cabrera-Pérez M.A., González M.P. (2006) A radial-distribution-function approach for predicting rodent carcinogenicity. J Mol Model 12 : 769 780.
    • (2006) J Mol Model , vol.12 , pp. 769-780
    • Helguera, A.M.1    Cabrera-Pérez, M.A.2    González, M.P.3
  • 42
    • 33751032263 scopus 로고    scopus 로고
    • Ensembles of Bayesian-regularized genetic neural networks for modeling of acetylcholinesterase inhibition by huprines
    • Fernández M., Caballero J. (2006) Ensembles of Bayesian-regularized genetic neural networks for modeling of acetylcholinesterase inhibition by huprines. Chem Biol Drug Des 68 : 201 212.
    • (2006) Chem Biol Drug des , vol.68 , pp. 201-212
    • Fernández, M.1    Caballero, J.2
  • 43
    • 33845769362 scopus 로고    scopus 로고
    • Modeling of acetylcholinesterase inhibition by tacrine analogues using Bayesian-regularized genetic neural networks and ensemble averaging
    • Fernández M., Carreiras M.C., Marco J.L., Caballero J. (2006) Modeling of acetylcholinesterase inhibition by tacrine analogues using Bayesian-regularized genetic neural networks and ensemble averaging. J Enzyme Inhib Med Chem 21 : 647 661.
    • (2006) J Enzyme Inhib Med Chem , vol.21 , pp. 647-661
    • Fernández, M.1    Carreiras, M.C.2    Marco, J.L.3    Caballero, J.4
  • 44
    • 35449002457 scopus 로고    scopus 로고
    • Protein radial distribution function (P-RDF) and Bayesian-regularized genetic neural networks for modeling protein conformational stability: Chymotrypsin inhibitor 2 mutants
    • Fernández M., Caballero J., Fernández L., Abreu J.I., Garriga M. (2007) Protein radial distribution function (P-RDF) and Bayesian-regularized genetic neural networks for modeling protein conformational stability: chymotrypsin inhibitor 2 mutants. J Mol Graph Model 26 : 748 759.
    • (2007) J Mol Graph Model , vol.26 , pp. 748-759
    • Fernández, M.1    Caballero, J.2    Fernández, L.3    Abreu, J.I.4    Garriga, M.5
  • 45
    • 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
  • 47
    • 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


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