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Volumn 74, Issue 4, 2009, Pages 405-415

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

Author keywords

Arylsulfonylbenzonitriles; HIV 1 reverse transcriptase; Quantitative structure activity relationship; Substituent electronic descriptors

Indexed keywords

BENZONITRILE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

EID: 70349107717     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00871.x     Document Type: Article
Times cited : (7)

References (49)
  • 1
    • 0023026104 scopus 로고
    • Molecular cloning and polymorphism of the human immune deficiency virus type 2
    • Clavel F., Guyader M., Guetard M., Salle M., Montagnier L., Alizon M. (1986) Molecular cloning and polymorphism of the human immune deficiency virus type 2. Nature 324 : 691 695.
    • (1986) Nature , vol.324 , pp. 691-695
    • Clavel, F.1    Guyader, M.2    Guetard, M.3    Salle, M.4    Montagnier, L.5    Alizon, M.6
  • 2
    • 0023657622 scopus 로고
    • Genome organization and transactivation of the human immunodeficiency virus type 2
    • DOI 10.1038/326662a0
    • Guyader M., Emerman M., Sonigo P., Clavel F., Montagnier M., Alizon M. (1987) Genome organization and transactivation of the human immunodeficiency virus type 2. Nature 326 : 662 669. (Pubitemid 17059786)
    • (1987) Nature , vol.326 , Issue.6114 , pp. 662-669
    • Guyader, M.1    Emerman, M.2    Sonigo, P.3
  • 3
    • 0023852121 scopus 로고
    • The human immunodeficiency virus: Infectivity and mechanisms of pathogenesis
    • Fauci A.S. (1988) The human immunodeficiency virus: Infectivity and mechanisms of pathogenesis. Science 239 : 617 622.
    • (1988) Science , vol.239 , pp. 617-622
    • Fauci, A.S.1
  • 6
    • 0015251670 scopus 로고
    • RNA-dependent DNA polymerase activity of RNA tumor viruses. II. Directing influence of RNA in the reaction
    • Leis J.P., Hurwitz J. (1972) RNA-dependent DNA polymerase activity of RNA tumor viruses. II. Directing influence of RNA in the reaction. J Virol 9 : 130 142.
    • (1972) J Virol , vol.9 , pp. 130-142
    • Leis, J.P.1    Hurwitz, J.2
  • 9
    • 0034304841 scopus 로고    scopus 로고
    • New targets for inhibitors of HIV-1 replication
    • Moore J.P., Stevenson M. (2000) New targets for inhibitors of HIV-1 replication. Nat Rev Mol Cell Biol 1 : 40 49.
    • (2000) Nat Rev Mol Cell Biol , vol.1 , pp. 40-49
    • Moore, J.P.1    Stevenson, M.2
  • 10
    • 3042760870 scopus 로고    scopus 로고
    • Recent advances in the development of next generation non-nucleoside reverse transcriptase inhibitors
    • Tarby C.M. (2004) Recent advances in the development of next generation non-nucleoside reverse transcriptase inhibitors. Curr Top Med Chem 4 : 1045 1057.
    • (2004) Curr Top Med Chem , vol.4 , pp. 1045-1057
    • Tarby, C.M.1
  • 11
    • 32544442309 scopus 로고    scopus 로고
    • Next generation HIV-1 non-nucleoside reverses transcriptase inhibitors
    • Boone L.R. (2006) Next generation HIV-1 non-nucleoside reverses transcriptase inhibitors. Curr Opin Invest Drugs 7 : 128 135.
    • (2006) Curr Opin Invest Drugs , vol.7 , pp. 128-135
    • Boone, L.R.1
  • 12
    • 0032437454 scopus 로고    scopus 로고
    • The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • De Clercq E. (1998) The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection. Antiviral Res 38 : 153 179.
    • (1998) Antiviral Res , vol.38 , pp. 153-179
    • De Clercq, E.1
  • 13
    • 20144372481 scopus 로고    scopus 로고
    • In search of a novel anti-HIV drug: Multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoetenyl]-2-6-dimethylphenyl]amino]-2- pyrimidinyl]amino]-benzonitrile (R278474-rilpivirine)
    • Janssen P.A., Lewi P.J., Arnold E., Daeyaert F., De Jonge M., Heeres J., Koymans L. et al. (2005) In search of a novel anti-HIV drug: multidisciplinary coordination in the discovery of 4-[[4-[[4-[(1E)-2-cyanoetenyl]-2-6- dimethylphenyl]amino]-2-pyrimidinyl]amino]-benzonitrile (R278474-rilpivirine). J Med Chem 48 : 1901 1909.
    • (2005) J Med Chem , vol.48 , pp. 1901-1909
    • Janssen, P.A.1    Lewi, P.J.2    Arnold, E.3    Daeyaert, F.4    De Jonge, M.5    Heeres, J.6    Koymans, L.7
  • 14
    • 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
  • 15
    • 56649107750 scopus 로고    scopus 로고
    • Exploring QSAR for substituted 2-sulfonyl-phenyl-indol derivatives as potent and selective COX-2 inhibitors using different chemometrics tools
    • Khoshneviszadeh M., Edraki N., Miri R., Hemmateenejad B. (2008) Exploring QSAR for substituted 2-sulfonyl-phenyl-indol derivatives as potent and selective COX-2 inhibitors using different chemometrics tools. Chem Biol Drug Des 72 : 564 574.
    • (2008) Chem Biol Drug des , vol.72 , pp. 564-574
    • Khoshneviszadeh, M.1    Edraki, N.2    Miri, R.3    Hemmateenejad, B.4
  • 16
    • 0040914011 scopus 로고
    • ρ-σ-φ analysis. A method for the correlation of biological activity and chemical structure
    • Hansch C., Fujita T. (1964) ρ-σ-φ analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86 : 1616 1626.
    • (1964) J Am Chem Soc , vol.86 , pp. 1616-1626
    • Hansch, C.1    Fujita, T.2
  • 17
    • 0000652554 scopus 로고    scopus 로고
    • Comparative QSAR: Toward a deeper understanding of chemicobiological interactions
    • Hansch C., Hoekman D., Gao H. (1996) Comparative QSAR: toward a deeper understanding of chemicobiological interactions. Chem Rev 96 : 1045 1075.
    • (1996) Chem Rev , vol.96 , pp. 1045-1075
    • Hansch, C.1    Hoekman, D.2    Gao, H.3
  • 19
    • 40649101674 scopus 로고    scopus 로고
    • Modeling calcium channel antagonistic activity of dihydropyridine derivatives using QTMS indices analyzed by GA-PLS and PC-GA-PLS
    • Mohajeri A., Hemmateenejad B., Mehdipour A.R., Miri R. (2008) Modeling calcium channel antagonistic activity of dihydropyridine derivatives using QTMS indices analyzed by GA-PLS and PC-GA-PLS. J Mol Graph Model 26 : 1057 1065.
    • (2008) J Mol Graph Model , vol.26 , pp. 1057-1065
    • Mohajeri, A.1    Hemmateenejad, B.2    Mehdipour, A.R.3    Miri, R.4
  • 21
    • 34548784899 scopus 로고    scopus 로고
    • Substituent electronic descriptors for fast QSAR/QSPR
    • Hemmateenejad B., Sanchooli M. (2007) Substituent electronic descriptors for fast QSAR/QSPR. J. Chemom 21 : 96 107.
    • (2007) J. Chemom , vol.21 , pp. 96-107
    • Hemmateenejad, B.1    Sanchooli, M.2
  • 22
    • 69949157374 scopus 로고    scopus 로고
    • Application of MOLMAP approach for modeling of various biological activities using substituent electronic descriptors
    • Hemmateenejad B., Mehdipour A.R., Miri R., Shamsipur M. (2009) Application of MOLMAP approach for modeling of various biological activities using substituent electronic descriptors. J Comput Chem 30 : 2001 2009.
    • (2009) J Comput Chem , vol.30 , pp. 2001-2009
    • Hemmateenejad, B.1    Mehdipour, A.R.2    Miri, R.3    Shamsipur, M.4
  • 23
    • 60849112247 scopus 로고    scopus 로고
    • Predicting anti-HIV activity of 1,3,4-thiazolidinone derivatives: 3D-QSAR approach
    • Ravichandran V., Prashantha Kumar B.R., Sankar S., Agrawal R.K. (2009) Predicting anti-HIV activity of 1,3,4-thiazolidinone derivatives: 3D-QSAR approach. Eur J Med Chem 44 : 1180 1187.
    • (2009) Eur J Med Chem , vol.44 , pp. 1180-1187
    • Ravichandran, V.1    Prashantha Kumar, B.R.2    Sankar, S.3    Agrawal, R.K.4
  • 24
    • 0035263420 scopus 로고    scopus 로고
    • QSAR modeling with the electrotopological state: TIBO derivatives
    • Huuskonen J. (2001) QSAR modeling with the electrotopological state: TIBO derivatives. J Chem Inf Comput Sci 41 : 425 429.
    • (2001) J Chem Inf Comput Sci , vol.41 , pp. 425-429
    • Huuskonen, J.1
  • 25
    • 36549051716 scopus 로고    scopus 로고
    • Docking studies on the effect of beta-ring expantion in TIBO derivatives
    • Hemmateenejad B., Tabaei S M.H., Namvaran F. (2007) Docking studies on the effect of beta-ring expantion in TIBO derivatives. J Iran Chem Soc 4 : 481 489.
    • (2007) J Iran Chem Soc , vol.4 , pp. 481-489
    • Hemmateenejad, B.1    Tabaei, S.M.H.2    Namvaran, F.3
  • 26
    • 1542301644 scopus 로고    scopus 로고
    • QSAR study on some anti-HIV HEPT analogues using physicochemical and topological parameters
    • Gayen S., Debnath B., Samanta S., Jha T. (2004) QSAR study on some anti-HIV HEPT analogues using physicochemical and topological parameters. Bioorg Med Chem 12 : 1493 1503.
    • (2004) Bioorg Med Chem , vol.12 , pp. 1493-1503
    • Gayen, S.1    Debnath, B.2    Samanta, S.3    Jha, T.4
  • 27
    • 0842283490 scopus 로고    scopus 로고
    • QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners using molecular connectivity and E-state parameters
    • Roy K., Leonard J T.J. (2004) QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners using molecular connectivity and E-state parameters. Bioorg Med Chem 12 : 745 754.
    • (2004) Bioorg Med Chem , vol.12 , pp. 745-754
    • Roy, K.1    Leonard, J.T.J.2
  • 28
    • 37349040711 scopus 로고    scopus 로고
    • Predicting anti-HIV-1 activity of 6-arylbenzonitriles: Computational approach using superaugmented eccentric connectivity topochemical indices
    • Dureja H., Gupta S., Madan A.K. (2008) Predicting anti-HIV-1 activity of 6-arylbenzonitriles: computational approach using superaugmented eccentric connectivity topochemical indices. J Mol Graph Model 26 : 1020 1029.
    • (2008) J Mol Graph Model , vol.26 , pp. 1020-1029
    • Dureja, H.1    Gupta, S.2    Madan, A.K.3
  • 30
    • 0037061639 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase
    • Silvestri R., Artico M., De Martino D., Ragno R., Massa S., Loddo R., Murgioni C., Loi A.G., La Colla P., Pani A. (2002) Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5- nitroimidazoles targeted at the HIV-1 reverse transcriptase. J Med Chem 45 : 1567 1576.
    • (2002) J Med Chem , vol.45 , pp. 1567-1576
    • Silvestri, R.1    Artico, M.2    De Martino, D.3    Ragno, R.4    Massa, S.5    Loddo, R.6    Murgioni, C.7    Loi, A.G.8    La Colla, P.9    Pani, A.10
  • 31
    • 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
  • 32
    • 54249140977 scopus 로고    scopus 로고
    • Docking and quantitative structure-activity relationship studies for the bisphenylbenzimidazole family of non-nucleoside inhibitors of HIV-1 reverse transcriptase
    • Lagos C.F., Caballero J., Gonzalez-Nilo F.D., Pessoa-Mahana C.D., Perez-Acle T. (2008) Docking and quantitative structure-activity relationship studies for the bisphenylbenzimidazole family of non-nucleoside inhibitors of HIV-1 reverse transcriptase. Chem Biol Drug Des 72 : 360 369.
    • (2008) Chem Biol Drug des , vol.72 , pp. 360-369
    • Lagos, C.F.1    Caballero, J.2    Gonzalez-Nilo, F.D.3    Pessoa-Mahana, C.D.4    Perez-Acle, T.5
  • 33
    • 4344677342 scopus 로고    scopus 로고
    • QSAR modeling of anti-HIV activities of alkenyldiarylmethanes using topological and physicochemical descriptors
    • Leonard J., 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.1    Roy, K.2
  • 34
    • 37749030978 scopus 로고    scopus 로고
    • Molecular modeling studies on 2-amino-6-aryl-sulphonylbenzonitriles as non-nucleosode reverse transcriptase inhibitors of HIV-1: A QSAR approach
    • Sapre N., Pancholi N., Gupta S., Sikrwar A., Sapre N. (2007) Molecular modeling studies on 2-amino-6-aryl-sulphonylbenzonitriles as non-nucleosode reverse transcriptase inhibitors of HIV-1: a QSAR approach. J Chem Sci 119 : 625 630.
    • (2007) J Chem Sci , vol.119 , pp. 625-630
    • Sapre, N.1    Pancholi, N.2    Gupta, S.3    Sikrwar, A.4    Sapre, N.5
  • 35
    • 2942550228 scopus 로고    scopus 로고
    • Classical QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners
    • Leonard J.T., Roy K. (2004) Classical QSAR modeling of HIV-1 reverse transcriptase inhibitor 2-amino-6-arylsulfonylbenzonitriles and congeners. QSAR Comb Sci 23 : 23 35.
    • (2004) QSAR Comb Sci , vol.23 , pp. 23-35
    • Leonard, J.T.1    Roy, K.2
  • 36
    • 0035821597 scopus 로고    scopus 로고
    • 2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1
    • Chan J.H., Hong J.S., Hunter R.N., Orr G.F., Cowan J.R., Sherman D.B., Sparks S.M. et al. (2001) 2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1. J Med Chem 44 : 1866 1882.
    • (2001) J Med Chem , vol.44 , pp. 1866-1882
    • Chan, J.H.1    Hong, J.S.2    Hunter, R.N.3    Orr, G.F.4    Cowan, J.R.5    Sherman, D.B.6    Sparks, S.M.7
  • 38
    • 67649968067 scopus 로고    scopus 로고
    • Quantitative structure-reactivity relationship studies on the catalyzed Michael addition reactions
    • Hemmateenejad B., Sanchooli M., Mehdipour A.R. (2009) Quantitative structure-reactivity relationship studies on the catalyzed Michael addition reactions. J Phys Org Chem 22 : 613 618.
    • (2009) J Phys Org Chem , vol.22 , pp. 613-618
    • Hemmateenejad, B.1    Sanchooli, M.2    Mehdipour, A.R.3
  • 39
    • 0038031513 scopus 로고    scopus 로고
    • Application of quantum chemical descriptor in quantitative structure activity and structure property relationship
    • Thanikaivelan P., Subramanian V., Rao J.R., Nair B.U. (2000) Application of quantum chemical descriptor in quantitative structure activity and structure property relationship. Chem Phys Lett 323 : 59 70.
    • (2000) Chem Phys Lett , vol.323 , pp. 59-70
    • Thanikaivelan, P.1    Subramanian, V.2    Rao, J.R.3    Nair, B.U.4
  • 40
    • 0015417054 scopus 로고
    • Chance correlation structure-activity studies using multiple regression analysis
    • Topliss J.G., Costello R.J. (1972) Chance correlation structure-activity studies using multiple regression analysis. J Med Chem 15 : 1066 1078.
    • (1972) J Med Chem , vol.15 , pp. 1066-1078
    • Topliss, J.G.1    Costello, R.J.2
  • 41
    • 0018709674 scopus 로고
    • Chance factors in studies of quantitative structure-activity relationships
    • Topliss J.G., Edwards R.P. (1979) Chance factors in studies of quantitative structure-activity relationships. J Med Chem 22 : 1238 1244.
    • (1979) J Med Chem , vol.22 , pp. 1238-1244
    • Topliss, J.G.1    Edwards, R.P.2
  • 42
    • 33846877842 scopus 로고    scopus 로고
    • An improved approximation to the estimation of the critical F values in best subset regression
    • Salt D.W., Ajmani S., Crichton R., Livingstone D.J. (2007) An improved approximation to the estimation of the critical F values in best subset regression. J Chem Inf Model 47 : 143 149.
    • (2007) J Chem Inf Model , vol.47 , pp. 143-149
    • Salt, D.W.1    Ajmani, S.2    Crichton, R.3    Livingstone, D.J.4
  • 43
    • 58149498317 scopus 로고    scopus 로고
    • QSPR models for half-wave reduction potential of steroids: A comparative study between feature selection and feature extraction from subsets of or entire set of descriptors
    • Hemmateenejad B., Yazdani M. (2009) QSPR models for half-wave reduction potential of steroids: a comparative study between feature selection and feature extraction from subsets of or entire set of descriptors. Anal Chim Acta 634 : 27 35.
    • (2009) Anal Chim Acta , vol.634 , pp. 27-35
    • Hemmateenejad, B.1    Yazdani, M.2
  • 44
    • 33947329168 scopus 로고    scopus 로고
    • Effects of electronic and physicochemical parameters on the carcinogenic activity of some sulfa drugs using QSAR analysis based on genetic-MLR and genetic-PLS
    • Deeb O., Hemmateenejad B., Jaber A., Garduno-Juarez R., Miri R. (2007) Effects of electronic and physicochemical parameters on the carcinogenic activity of some sulfa drugs using QSAR analysis based on genetic-MLR and genetic-PLS. Chemosphere 67 : 2122 2130.
    • (2007) Chemosphere , vol.67 , pp. 2122-2130
    • Deeb, O.1    Hemmateenejad, B.2    Jaber, A.3    Garduno-Juarez, R.4    Miri, R.5
  • 45
    • 0033647286 scopus 로고    scopus 로고
    • Application of genetic algorithm-PLS for feature selection in spectral data sets
    • Leardi R. (2000) Application of genetic algorithm-PLS for feature selection in spectral data sets. J Chemom 14 : 643 655.
    • (2000) J Chemom , vol.14 , pp. 643-655
    • Leardi, R.1
  • 46
    • 0345019845 scopus 로고    scopus 로고
    • Genetic algorithms applied to feature selection in PLS regression: How and when to use them
    • Leardi R., Gonzalez A.L. (1998) Genetic algorithms applied to feature selection in PLS regression: how and when to use them. Chemom Intell Lab Syst 41 : 195 207.
    • (1998) Chemom Intell Lab Syst , vol.41 , pp. 195-207
    • Leardi, R.1    Gonzalez, A.L.2
  • 47
    • 0035960060 scopus 로고    scopus 로고
    • Quantitative structure-antitumor activity relationships of camptothecin analogues: Cluster analysis and genetic algorithm-based studies
    • Fan Y., Shi L.M., Kohn K.W., Pommier Y., Weinstein J.N. (2001) Quantitative structure-antitumor activity relationships of camptothecin analogues: cluster analysis and genetic algorithm-based studies. J Med Chem 44 : 3254 3263.
    • (2001) J Med Chem , vol.44 , pp. 3254-3263
    • Fan, Y.1    Shi, L.M.2    Kohn, K.W.3    Pommier, Y.4    Weinstein, J.N.5
  • 48
    • 0034868132 scopus 로고    scopus 로고
    • Genetic algorithms in chemometrics and chemistry: A review
    • Leardi R. (2001) Genetic algorithms in chemometrics and chemistry: a review. J Chemom 15 : 559 569.
    • (2001) J Chemom , vol.15 , pp. 559-569
    • Leardi, R.1
  • 49
    • 28444497469 scopus 로고    scopus 로고
    • Chance correlation in variable subset regression: Influence of the objective function, the selection mechanism, and ensemble averaging
    • Baumann K. (2005) Chance correlation in variable subset regression: Influence of the objective function, the selection mechanism, and ensemble averaging. QSAR Comb Sci 9 : 1033 1046.
    • (2005) QSAR Comb Sci , vol.9 , pp. 1033-1046
    • Baumann, K.1


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