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Volumn 54, Issue 6, 2011, Pages 1587-1598

Indolylarylsulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors: New cyclic substituents at indole-2-carboxamide

Author keywords

[No Author keywords available]

Indexed keywords

3 [(3,5 DIMETHYLPHENYL)SULFONYL] 5 NITRO 1H INDOLE 2 CARBOXAMIDE; 5 BROMO 3 [(3,5 DIMETHYLPHENYL)SULFONYL] N (PYRROLIDIN 1 YLMETHYL) 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 [(3,5 DIMETHYLPHENYL)SULFONYL] N (PYRROLIDIN 1 YLMETHYL) 1H INDOLE 2 CARBOXAMIDE; AMIDE; CARBENE; EFAVIRENZ; ETHYLENE; ETRAVIRINE; GLUTAMIC ACID; HISTIDINE; HYDROGEN; INDOLYLARYLSULFONE DERIVATIVE; LEUCINE; N BENZYL 5 CHLORO 3 [(3,5 DIMETHYLPHENYL)SULFONYL] 1H INDOLE 2 CARBOXAMIDE; N BENZYL 5 CHLORO 3 [(3,5 DIMETHYLPHENYL)SULFONYL] 4 FLUORO 1H INDOLE 2 CARBOXAMIDE; NEVIRAPINE; NITROGEN; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PHENYLALANINE; PROLINE; RNA DIRECTED DNA POLYMERASE; TYROSINE; UNCLASSIFIED DRUG; VALINE;

EID: 79952792724     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101614j     Document Type: Article
Times cited : (155)

References (58)
  • 1
    • 0020596551 scopus 로고
    • Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS)
    • Barre-Sinoussi, F.; Chermann, J.; Rey, F.; Nugeyre, M.; Chamaret, S.; Gruest, J.; Dauguet, C.; Axler-Blin, C.; Vezinet-Brun, F.; Rouzioux, C.; Rozenbaum, W.; Montagnier, L. Isolation of a T-lymphotric retrovirus from a patient for a risk of acquired immunodeficiency syndrome (AIDS) Science 1983, 220, 868-871 (Pubitemid 13080157)
    • (1983) Science , vol.220 , Issue.4599 , pp. 868-871
    • Barre Sinoussi, F.1    Chermann, J.C.2    Rey, F.3
  • 2
    • 0020532060 scopus 로고
    • Isolation of human T-cell leukemia virus in acquired immune deficiency syndrome (AIDS)
    • Gallo, R. C.; Sarin, P. S.; Gelmann, E. P.; Robert-Guroff, M.; Richardson, E.; Kalyanaraman, V. S.; Mann, D.; Sidhu, G. D.; Stahl, R. E.; Zolla.Pazner, S.; Leibowitch, J.; Popovic, M. Isolation of human T-cell leukemia virus in acquired mmunodeficiency syndrome (AIDS) Science 1983, 220, 865-867 (Pubitemid 13080156)
    • (1983) Science , vol.220 , Issue.4599 , pp. 865-867
    • Gallo, R.C.1    Sarin, P.S.2    Gelmann, E.P.3
  • 3
    • 79952800819 scopus 로고    scopus 로고
    • 2009 AIDS epidemic update.
    • 2009 AIDS epidemic update.
  • 4
    • 77249134151 scopus 로고    scopus 로고
    • Twenty-six years of anti-HIV drug discovery: Where do we stand and where do we go
    • Mehellou, Y.; De Clercq, E. Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go- J. Med. Chem. 2010, 53, 521-538
    • (2010) J. Med. Chem. , vol.53 , pp. 521-538
    • Mehellou, Y.1    De Clercq, E.2
  • 5
    • 77649202344 scopus 로고    scopus 로고
    • Highlights in the discovery of antiviral drugs: A personal retrospective
    • De Clercq, E. Highlights in the discovery of antiviral drugs: a personal retrospective J. Med. Chem. 2010, 53, 1438-1450
    • (2010) J. Med. Chem. , vol.53 , pp. 1438-1450
    • De Clercq, E.1
  • 6
    • 73549089480 scopus 로고    scopus 로고
    • Current status and challenges of antiretroviral research and therapy
    • Este, J. A.; Cihlar, T. Current status and challenges of antiretroviral research and therapy Antiviral Res. 2010, 85, 25-33
    • (2010) Antiviral Res. , vol.85 , pp. 25-33
    • Este, J.A.1    Cihlar, T.2
  • 7
    • 73549088708 scopus 로고    scopus 로고
    • Molecular basis of human immunodeficiency virus drug resistance: An update
    • Menéndez-Arias, L. Molecular basis of human immunodeficiency virus drug resistance: an update Antiviral Res. 2010, 85, 210-231
    • (2010) Antiviral Res. , vol.85 , pp. 210-231
    • Menéndez-Arias, L.1
  • 8
    • 73549084507 scopus 로고    scopus 로고
    • Clinical management of HIV-1 resistance
    • Paredes, R.; Clotet, B. Clinical management of HIV-1 resistance Antiviral Res. 2010, 85, 245-265
    • (2010) Antiviral Res. , vol.85 , pp. 245-265
    • Paredes, R.1    Clotet, B.2
  • 9
    • 73549101316 scopus 로고    scopus 로고
    • Understanding and managing the adverse effects of antiretroviral therapy
    • Hawkins, T. Understanding and managing the adverse effects of antiretroviral therapy Antiviral Res. 2010, 85, 201-209
    • (2010) Antiviral Res. , vol.85 , pp. 201-209
    • Hawkins, T.1
  • 11
    • 46749104685 scopus 로고    scopus 로고
    • Improving non-nucleoside reverse transcriptase inhibitors for first-line treatment of HIV infection: The development pipeline and recent clinical data
    • Sweeney1, Z. K.; Klumpp, K. Improving non-nucleoside reverse transcriptase inhibitors for first-line treatment of HIV infection: the development pipeline and recent clinical data Curr. Opin. Drug Discovery Dev. 2008, 11, 454-470
    • (2008) Curr. Opin. Drug Discovery Dev. , vol.11 , pp. 454-470
    • Sweeney, Z.K.1    Klumpp, K.2
  • 12
    • 26444595584 scopus 로고    scopus 로고
    • TMC125 displays a high genetic barrier to the development of resistance: Evidence from in vitro selection experiments
    • DOI 10.1128/JVI.79.20.12773-12782.2005
    • Vingerhoets, J.; Azijn, H.; Fransen, E.; De Baere, I.; Smeulders, L.; Jochmans, D.; Andries, K.; Pauwels, R.; de Bethune, M.-P. TMC125 displays a high genetic barrier to the development of resistance: evidence from in vitro selection experiments J. Virol. 2005, 79, 12773-12782 (Pubitemid 41433197)
    • (2005) Journal of Virology , vol.79 , Issue.20 , pp. 12773-12782
    • Vingerhoets, J.1    Azijn, H.2    Fransen, E.3    De Baere, I.4    Smeulders, L.5    Jochmans, D.6    Andries, K.7    Pauwels, R.8    De Bethune, M.-P.9
  • 17
    • 3142651936 scopus 로고    scopus 로고
    • Simple, short peptide derivatives of a sulfonylindolecarboxamide (L-737,126) active in vitro against HIV-1 wild type and variants carrying non-nucleoside reverse transcriptase inhibitor resistance mutations
    • DOI 10.1021/jm031147e
    • Silvestri, R.; Artico, M.; De Martino, G.; La Regina, G.; Loddo, R.; La Colla, M.; La Colla, P. Simple, short peptide derivatives of a sulfonylindolecarboxamide (L-737,126) active in vitro against HIV-1 wild-type and variants carrying non-nucleoside reverse transcriptase inhibitor resistance mutations J. Med. Chem. 2004, 47, 3892-3896 (Pubitemid 38900354)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.15 , pp. 3892-3896
    • Silvestri, R.1    Artico, M.2    De Martino, G.3    La Regina, G.4    Loddo, R.5    La Colla, M.6    La Colla, P.7
  • 24
    • 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
    • DOI 10.1021/jm040854k
    • Ragno, R.; Artico, M.; De Martino, G.; La Regina, G.; Coluccia, A.; Di Pasquali, A.; Silvestri, R. Docking and 3-D QSAR studies on indolyl aryl sulfones (IASs). Binding mode exploration at the HIV-1 reverse transcriptase non-nucleoside binding site and design of highly active N -(2-hydroxyethyl) carboxyamide and N -(2-hydroxyethyl)carboxyhydrazide derivatives J. Med. Chem. 2005, 48, 213-223 (Pubitemid 40109512)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.1 , 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
  • 25
    • 33646455456 scopus 로고    scopus 로고
    • Indolyl aryl sulfones (IASs) as HIV-1 non-nucleoside reverse transcriptase inhibitors. Synthesis, biological evaluation and binding mode studies of new derivatives at indole-2-carboxamide
    • De Martino, G.; La Regina, G.; Ragno, R.; Coluccia, A.; Bergamini, A.; Ciaprini, C.; Sinistro, A.; Maga, G.; Crespan, E.; Artico, M.; Silvestri., R. Indolyl aryl sulfones (IASs) as HIV-1 non-nucleoside reverse transcriptase inhibitors. Synthesis, biological evaluation and binding mode studies of new derivatives at indole-2-carboxamide Antiviral Chem. Chemother. 2006, 17, 59-77
    • (2006) Antiviral Chem. Chemother. , vol.17 , pp. 59-77
    • De Martino, G.1    La Regina, G.2    Ragno, R.3    Coluccia, A.4    Bergamini, A.5    Ciaprini, C.6    Sinistro, A.7    Maga, G.8    Crespan, E.9    Artico, M.10    Silvestri, R.11
  • 27
    • 79952793240 scopus 로고    scopus 로고
    • Lead-likenss and Drug-likeness
    • 3 rd ed.; Wermuth C. G. Elsevier Ltd.: Oxford, U.K.
    • Polinsky, A. Lead-likenss and Drug-likeness. In The Practice of Medicinal Chemistry, 3 rd ed.; Wermuth C. G. Elsevier Ltd.: Oxford, U.K., 2008; pp 244 - 254.
    • (2008) The Practice of Medicinal Chemistry , pp. 244-254
    • Polinsky, A.1
  • 29
    • 79952806086 scopus 로고    scopus 로고
    • The recombinant HIV-1 RT carrying the Y181I mutation was comparable to the Y181C substitution in terms of drug resistance, from an enzymological point of view. See ref 17.
    • The recombinant HIV-1 RT carrying the Y181I mutation was comparable to the Y181C substitution in terms of drug resistance, from an enzymological point of view. See ref 17.
  • 30
    • 0036987892 scopus 로고    scopus 로고
    • Discovery of second generation of quinazoline non-nucleoside reverse transcriptase inhibitors of HIV-1
    • Corbett, J. W.; Rodgers, J. D. Discovery of second generation of quinazoline non-nucleoside reverse transcriptase inhibitors of HIV-1 Prog. Med. Chem. 2002, 40, 63-105
    • (2002) Prog. Med. Chem. , vol.40 , pp. 63-105
    • Corbett, J.W.1    Rodgers, J.D.2
  • 31
    • 79952810859 scopus 로고    scopus 로고
    • ALOGPS and ALOGpS values were calculated at the Web site using ALOGPS version 2.1
    • ALOGPS and ALOGpS values were calculated at the Web site www.vcclab.org using ALOGPS version 2.1
  • 33
    • 79952798246 scopus 로고    scopus 로고
    • VCCLAB, Virtual Computational Chemistry Laboratory.
    • VCCLAB, Virtual Computational Chemistry Laboratory. http://www.vcclab. org.
  • 35
    • 1342321756 scopus 로고    scopus 로고
    • Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives: Synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus
    • DOI 10.1016/j.farmac.2003.11.004
    • Silvestri, R.; Artico, M.; La Regina, G.; De Martino, G.; La Colla, M.; Loddo, R.; La Colla, P. Anti-HIV-1 activity of pyrryl aryl sulfone (PAS) derivatives. Synthesis and SAR studies of novel esters and amides at the position 2 of the pyrrole nucleus Farmaco 2004, 59, 201-210 (Pubitemid 38251617)
    • (2004) Farmaco , vol.59 , Issue.3 , pp. 201-210
    • Silvestri, R.1    Artico, M.2    La Regina, G.3    De Martino, G.4    La Colla, M.5    Loddo, R.6    La Colla, P.7
  • 37
    • 77956900680 scopus 로고    scopus 로고
    • Looking for an active conformation of the future HIV-1 non-nucleoside reverse transcriptase inhibitors
    • La Regina, G.; Coluccia, A.; Silvestri, R. Looking for an active conformation of the future HIV-1 non-nucleoside reverse transcriptase inhibitors Antiviral Chem. Chemother. 2010, 20, 231-237
    • (2010) Antiviral Chem. Chemother. , vol.20 , pp. 231-237
    • La Regina, G.1    Coluccia, A.2    Silvestri, R.3
  • 40
    • 79952787584 scopus 로고    scopus 로고
    • version 2.2; BioSolveIT GmbH: Sankt Augustin, Germany.
    • FlexX version 2.2; BioSolveIT GmbH: Sankt Augustin, Germany; http://www.biosolveit.de/FlexX/.
    • FlexX
  • 41
    • 0004313709 scopus 로고    scopus 로고
    • version 2009.10; Chemical Computing Group Inc.: Montreal, Canada
    • Molecular Operating Environment (MOE) version 2009.10; Chemical Computing Group Inc.: Montreal, Canada; http://www.chemcomp.com/.
    • Molecular Operating Environment (MOE)
  • 43
    • 0026693137 scopus 로고
    • Crystal structure at 3.5 A... resolution of HIV-1 reverse transcriptase complexed with an inhibitor
    • Kohlstaedt, L. A.; Wang, J.; Friedman, J. M.; Rice, P. A.; Steitz, T. A. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor Science 1992, 256, 1783-1790
    • (1992) Science , vol.256 , pp. 1783-1790
    • Kohlstaedt, L.A.1    Wang, J.2    Friedman, J.M.3    Rice, P.A.4    Steitz, T.A.5
  • 45
    • 0034435564 scopus 로고    scopus 로고
    • Structural basis for the resilience of efavirenz (DMP-266) to drug resistance mutations in HIV-1 reverse transcriptase
    • DOI 10.1016/S0969-2126(00)00513-X, PII S096921260000513X
    • Ren, J.; Milton, J.; Weaver, K. L.; Short, S. A.; Stuart, D. I.; Stammers, D. K. Structural basis for the resilience of efavirenz (DMP-266) to drug resistance mutations in HIV-1 reverse transcriptase Structure 2000, 8, 1089-1094 (Pubitemid 32667472)
    • (2000) Structure , vol.8 , Issue.10 , pp. 1089-1094
    • Ren, J.1    Milton, J.2    Weaver, K.L.3    Short, S.A.4    Stuart, D.I.5    Stammers, D.K.6
  • 46
    • 0842289678 scopus 로고    scopus 로고
    • Crystal Structures of HIV-1 Reverse Transcriptases Mutated at Codons 100, 106 and 108 and Mechanisms of Resistance to Non-nucleoside Inhibitors
    • DOI 10.1016/j.jmb.2003.12.055
    • Ren, J.; Nichols, C. E.; Chamberlain, P. P.; Weaver, K. L.; Short, S. A.; Stammers, D. K. Crystal structures of HIV-1 reverse transcriptases mutated at codons 100, 106 and 108 and mechanisms of resistance to non-nucleoside inhibitors J. Mol. Biol. 2004, 336, 569-578 (Pubitemid 38183013)
    • (2004) Journal of Molecular Biology , vol.336 , Issue.3 , pp. 569-578
    • Ren, J.1    Nichols, C.E.2    Chamberlain, P.P.3    Weaver, K.L.4    Short, S.A.5    Stammers, D.K.6
  • 47
    • 34248998744 scopus 로고    scopus 로고
    • Relationship of potency and resilience to drug resistant mutations for GW420867X revealed by crystal structures of inhibitor complexes for wild-type, Leu100Ile, Lys101Glu, and Tyr188Cys mutant HIV-1 reverse transcriptases
    • DOI 10.1021/jm061117m
    • Ren, J.; Nichols, C. E.; Chamberlain, P. P.; Weaver, K. L.; Short, S. A.; Chan, J. H.; Kleim, J. P.; Stammers, D. K. Relationship of potency and resilience to drug resistant mutations for GW420867X revealed by crystal structures of inhibitor complexes for wild-type, Leu100Ile, Lys101Glu, and Tyr188Cys mutant HIV-1 reverse transcriptases J. Med. Chem. 2007, 50, 2301-2309 (Pubitemid 46799242)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.10 , pp. 2301-2309
    • Ren, J.1    Nichols, C.E.2    Chamberlain, P.P.3    Weaver, K.L.4    Short, S.A.5    Chan, J.H.6    Kleim, J.-P.7    Stammers, D.K.8
  • 48
    • 0035965124 scopus 로고    scopus 로고
    • Structural mechanisms of drug resistance for mutations at codons 181 and 188 in HIV-1 reverse transcriptase and the improved resilience of second generation non-nucleoside inhibitors
    • DOI 10.1006/jmbi.2001.4988
    • Ren, J.; Nichols, C.; Bird, L.; Chamberlain, P.; Weaver, K.; Short, S.; Stuart, D. I.; Stammers, D. K. Structural mechanisms of drug resistance for mutations at codons 181 and 188 in HIV-1 reverse transcriptase and the improved resilience of second generation non-nucleoside inhibitors J. Mol. Biol. 2001, 312, 795-805 (Pubitemid 33116741)
    • (2001) Journal of Molecular Biology , vol.312 , Issue.4 , pp. 795-805
    • Ren, J.1    Nichols, C.2    Bird, L.3    Chamberlain, P.4    Weaver, K.5    Short, S.6    Stuart, D.I.7    Stammers, D.K.8
  • 49
    • 79952779562 scopus 로고    scopus 로고
    • Code "scoring.svl" was obtained from SLV Exchange Web site (Chemical Computing Group, Inc., Montreal, Canada).
    • Code "scoring.svl" was obtained from SLV Exchange Web site http://svl.chemcomp.com (Chemical Computing Group, Inc., Montreal, Canada).
  • 51
    • 0037495965 scopus 로고    scopus 로고
    • Development of polyphosphate parameters for use with the AMBER force field
    • Meagher, K. L.; Redman, L. T.; Carlson, H. A. Development of polyphosphate parameters for use with the AMBER force field J. Comput. Chem. 2003, 24, 1016-1026
    • (2003) J. Comput. Chem. , vol.24 , pp. 1016-1026
    • Meagher, K.L.1    Redman, L.T.2    Carlson, H.A.3
  • 52
    • 33748538349 scopus 로고    scopus 로고
    • Automatic atom type and bond type perception in molecular mechanical calculations
    • DOI 10.1016/j.jmgm.2005.12.005, PII S1093326305001737
    • Wang, J.; Wang, W.; Kollman, P. A.; Case, D. A. Automatic atom type and bond type perception in molecular mechanical calculations J. Mol. Graph. Model. 2006, 25, 247-260 (Pubitemid 44363172)
    • (2006) Journal of Molecular Graphics and Modelling , vol.25 , Issue.2 , pp. 247-260
    • Wang, J.1    Wang, W.2    Kollman, P.A.3    Case, D.A.4
  • 54
    • 79952804940 scopus 로고    scopus 로고
    • version 1.4.
    • AmberTools version 1.4; http://ambermd.org/#AmberTools.
    • AmberTools
  • 55
    • 79952808763 scopus 로고    scopus 로고
    • version 1.2r1; DeLano Scientific LLC: San Carlos, CA.
    • PyMOL version 1.2r1; DeLano Scientific LLC: San Carlos, CA http://www.pymol.org/.
    • PyMOL
  • 57
    • 40749129190 scopus 로고    scopus 로고
    • Tetrazolium-based colorimetric assay for the detection of HIV replication inhibitors: Revisited 20 years later
    • DOI 10.1038/nprot.2007.517, PII NPROT.2007.517
    • Pannecouque, C.; Daelemans, D.; De Clercq, E. Tetrazolum-based colometric assay for the detection of HIV replication inhibitors: revised 20 years latter Nat. Protoc. 2008, 3, 427-434 (Pubitemid 351384256)
    • (2008) Nature Protocols , vol.3 , Issue.3 , pp. 427-434
    • Pannecouque, C.1    Daelemans, D.2    De Clercq, E.3
  • 58
    • 0031578901 scopus 로고    scopus 로고
    • Resistance to Nevirapine of HIV-1 reverse transcriptase mutants: Loss of stabilizing interactions and thermodynamic or steric barriers are induced by different single amino acid substitutions
    • DOI 10.1006/jmbi.1997.1427
    • Maga, G.; Amacker, M.; Ruel, N.; Hubsher, U.; Spadari, S. Resistance to nevirapine of HIV-1 reverse transcriptase mutants: loss of stabilizing interactions and thermodynamic or steric barriers are induced by different single amino acid substitutions J. Mol. Biol. 1997, 274, 738-747 (Pubitemid 28021342)
    • (1997) Journal of Molecular Biology , vol.274 , Issue.5 , pp. 738-747
    • Maga, G.1    Amacker, M.2    Ruel, N.3    Hubscher, U.4    Spadari, S.5


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