메뉴 건너뛰기




Volumn 53, Issue 13, 2010, Pages 4906-4916

Diarylaniline derivatives as a distinct class of HIV-1 non-nucleoside reverse transcriptase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIARYLBENZENE 1,2 DIAMINE DERIVATIVE; 5 (4'' BROMO 2'',6'' DIMETHYLPHENOXY) N1 (4' CYANOPHENYL) 4 NITROBENZENE 1,2 DIAMINE; 5 (4'' CYANO 2'',6'' DIMETHYLPHENOXY) N (4' CYANOPHENYL) 2,4 DINITROANILINE; 5 (4'' CYANO 2'',6'' DIMETHYLPHENOXY) N1 (4' CYANOPHENYL) 4 NITROBENZENE 1,2 DIAMINE; 5 (4'' CYANO 2'',6'' DIMETHYLPHENOXY) N1 (4' CYANOPHENYL)BENZENE 1,2,4 TRIAMINE; ANILINE DERIVATIVE; DIAMINE DERIVATIVE; ETRAVIRINE; NEVIRAPINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; RILPIVIRINE; UNCLASSIFIED DRUG; ZIDOVUDINE;

EID: 77954338696     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1002952     Document Type: Article
Times cited : (54)

References (43)
  • 1
    • 0028172345 scopus 로고
    • Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptase: Implications for mechanisms of drug inhibition and resistance
    • Tantillo, C.; Ding, J. P.; Jacobo-Molina, A.; Nanni, R. G.; Boyer, P. L.; Hughes, S. H.; Pauwels, R.; Andries, K.; Janssen, P. A. J.; Arnold, E. Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptase: implications for mechanisms of drug inhibition and resistance J. Mol. Biol. 1994, 243, 369-387
    • (1994) J. Mol. Biol. , vol.243 , pp. 369-387
    • Tantillo, C.1    Ding, J.P.2    Jacobo-Molina, A.3    Nanni, R.G.4    Boyer, P.L.5    Hughes, S.H.6    Pauwels, R.7    Andries, K.8    Janssen, P.A.J.9    Arnold, E.10
  • 2
    • 15444370583 scopus 로고    scopus 로고
    • New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections
    • Pauwels, R. New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections Curr. Opin. Pharmacol. 2004, 4, 437-446
    • (2004) Curr. Opin. Pharmacol. , vol.4 , pp. 437-446
    • Pauwels, R.1
  • 5
    • 61449189645 scopus 로고    scopus 로고
    • Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV
    • De Clercq, E. Anti-HIV drugs: 25 compounds approved within 25 years after the discovery of HIV Int. J. Antimicrob. Agents 2009, 33, 307-320
    • (2009) Int. J. Antimicrob. Agents , vol.33 , pp. 307-320
    • De Clercq, E.1
  • 9
    • 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. 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. 2005, 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
  • 10
    • 15444380338 scopus 로고    scopus 로고
    • From 4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1- jk ](1,4)benzodiazepin- 2(1 H)-one (TIBO) to Etravirine (TMC125): Fifteen Years of Research on Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase
    • De Corte, B. L. From 4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1- jk ](1,4)benzodiazepin- 2(1 H)-one (TIBO) to Etravirine (TMC125): Fifteen Years of Research on Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase J. Med. Chem. 2005, 48, 1689-1696
    • (2005) J. Med. Chem. , vol.48 , pp. 1689-1696
    • De Corte, B.L.1
  • 12
    • 40349091258 scopus 로고    scopus 로고
    • High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: Strategic flexibility explains potency against resistance mutations
    • Das, K.; Bauman, J. D.; Clark, A. D.; Frenkel, Y. V.; Lewi, P. J.; Shatkin, A. J.; Hughes, S. H.; Arnold, E. High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 1466-1471
    • (2008) Proc. Natl. Acad. Sci. U.S.A. , vol.105 , pp. 1466-1471
    • Das, K.1    Bauman, J.D.2    Clark, A.D.3    Frenkel, Y.V.4    Lewi, P.J.5    Shatkin, A.J.6    Hughes, S.H.7    Arnold, E.8
  • 16
    • 33746659068 scopus 로고    scopus 로고
    • Recent progress in diaryl ether synthesis
    • Frlan, R.; Kikelj, D. Recent progress in diaryl ether synthesis Synthesis 2006, 14, 2271-2285
    • (2006) Synthesis , vol.14 , pp. 2271-2285
    • Frlan, R.1    Kikelj, D.2
  • 17
    • 0141630561 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of diaryl ethers without catalyst
    • Li, F.; Wang, Q. R.; Ding, Z. B.; Tao, F. G. Microwave-assisted synthesis of diaryl ethers without catalyst Org. Lett. 2003, 5, 2169-2171
    • (2003) Org. Lett. , vol.5 , pp. 2169-2171
    • Li, F.1    Wang, Q.R.2    Ding, Z.B.3    Tao, F.G.4
  • 19
    • 68949110165 scopus 로고    scopus 로고
    • Discovery of diarylpyridine derivatives as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Tian, X. T.; Qin, B. J.; Lu, H.; Lai, W. H.; Jiang, S.; Lee, K. H.; Chen, C. H.; Xie, L. Discovery of diarylpyridine derivatives as novel non-nucleoside HIV-1 reverse transcriptase inhibitors Bioorg. Med. Chem. Lett. 2009, 19, 5482-5485
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 5482-5485
    • Tian, X.T.1    Qin, B.J.2    Lu, H.3    Lai, W.H.4    Jiang, S.5    Lee, K.H.6    Chen, C.H.7    Xie, L.8
  • 20
    • 0043245780 scopus 로고    scopus 로고
    • Insights into protein-protein binding by binding free energy calculation and free energy decomposition for the Ras-Raf and Ras-RalGDS complexes
    • Gohlke, H.; Kiel, C.; Case, D. A. Insights into protein-protein binding by binding free energy calculation and free energy decomposition for the Ras-Raf and Ras-RalGDS complexes J. Mol. Biol. 2003, 330, 891-913
    • (2003) J. Mol. Biol. , vol.330 , pp. 891-913
    • Gohlke, H.1    Kiel, C.2    Case, D.A.3
  • 21
    • 33846881144 scopus 로고    scopus 로고
    • Comparative evaluation of MMPBSA and XSCORE to compute binding free energy in XIAP-peptide complexes
    • Obiol-Pardo, C.; Rubio-Martinez, J. Comparative evaluation of MMPBSA and XSCORE to compute binding free energy in XIAP-peptide complexes J. Chem. Inf. Model. 2007, 47, 134-142
    • (2007) J. Chem. Inf. Model. , vol.47 , pp. 134-142
    • Obiol-Pardo, C.1    Rubio-Martinez, J.2
  • 22
    • 45749138489 scopus 로고    scopus 로고
    • MM-GB/SA rescoring of docking poses in structure-based lead optimization
    • Guimaraes, C. R.; Cardozo, M. MM-GB/SA rescoring of docking poses in structure-based lead optimization J. Chem. Inf. Model. 2008, 48, 958-970
    • (2008) J. Chem. Inf. Model. , vol.48 , pp. 958-970
    • Guimaraes, C.R.1    Cardozo, M.2
  • 25
    • 23844440296 scopus 로고    scopus 로고
    • Identification of N -phenyl- N ′-(2,2,6,6-tetramethylpiperidin-4- yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4
    • Zhao, Q.; Ma, L.; Jiang, S.; Lu, H.; Liu, S.; He, Y.; Strick, N.; Neamati, N.; Debnath, A. K. Identification of N -phenyl- N ′-(2,2,6,6- tetramethylpiperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4 Virology 2005, 339, 213-225
    • (2005) Virology , vol.339 , pp. 213-225
    • Zhao, Q.1    Ma, L.2    Jiang, S.3    Lu, H.4    Liu, S.5    He, Y.6    Strick, N.7    Neamati, N.8    Debnath, A.K.9
  • 26
    • 0021118703 scopus 로고
    • Quantitative analysis of dose-effect relationships: The combined effects of multiple drugs or enzyme inhibitors
    • Chou, T. C.; Talalay, P. Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors Adv. Enzyme Regul. 1984, 22, 27-55
    • (1984) Adv. Enzyme Regul. , vol.22 , pp. 27-55
    • Chou, T.C.1    Talalay, P.2
  • 27
    • 33746919528 scopus 로고    scopus 로고
    • Most multidrug-resistant HIV-1 reverse transcriptase clones in plasma encode functional reverse transcriptase enzymes
    • Dupnik, K. M.; Gonzales, M. J.; Shafer, R. W. Most multidrug-resistant HIV-1 reverse transcriptase clones in plasma encode functional reverse transcriptase enzymes Antivir. Ther. 2001, 6, 41-46
    • (2001) Antivir. Ther. , vol.6 , pp. 41-46
    • Dupnik, K.M.1    Gonzales, M.J.2    Shafer, R.W.3
  • 28
    • 24744455492 scopus 로고    scopus 로고
    • Tripos Inc.: 1699 South Hanley Road, St Louis, MO 63144
    • SYBYL 7.0; Tripos Inc.: 1699 South Hanley Road, St Louis, MO 63144.
    • SYBYL 7.0
  • 30
    • 0842341771 scopus 로고
    • AM1: A new general purpose quantum mechanical molecular model
    • Dewar, M.; Zoebisch, E.; Healy, E.; Stewart, J. AM1: A new general purpose quantum mechanical molecular model J. Am. Chem. Soc. 1985, 107, 3902-3909
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.1    Zoebisch, E.2    Healy, E.3    Stewart, J.4
  • 31
    • 0001041959 scopus 로고    scopus 로고
    • Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method
    • Jakalian, A.; Bush, B. L.; Jack, D. B.; Bayly, C. I. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method J. Comput. Chem. 2000, 21, 132-146
    • (2000) J. Comput. Chem. , vol.21 , pp. 132-146
    • Jakalian, A.1    Bush, B.L.2    Jack, D.B.3    Bayly, C.I.4
  • 32
    • 0036890178 scopus 로고    scopus 로고
    • Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation
    • Jakalian, A.; Jack, D. B.; Bayly, C. I. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: II. Parameterization and validation J. Comput. Chem. 2002, 23, 1623-1641
    • (2002) J. Comput. Chem. , vol.23 , pp. 1623-1641
    • Jakalian, A.1    Jack, D.B.2    Bayly, C.I.3
  • 35
    • 0032319206 scopus 로고    scopus 로고
    • Calculations of proton-binding thermodynamics in proteins
    • Beroza, P.; Case, D. Calculations of proton-binding thermodynamics in proteins Methods Enzymol. 1998, 295, 170-189
    • (1998) Methods Enzymol. , vol.295 , pp. 170-189
    • Beroza, P.1    Case, D.2
  • 36
    • 84961981091 scopus 로고    scopus 로고
    • Implicit solvation models: Equilibria, structure, spectra, and dynamics
    • Cramer, C. J.; Truhlar, D. G. Implicit solvation models: equilibria, structure, spectra, and dynamics Chem. Rev. 1999, 99, 2161-2200
    • (1999) Chem. Rev. , vol.99 , pp. 2161-2200
    • Cramer, C.J.1    Truhlar, D.G.2
  • 37
    • 0029066848 scopus 로고
    • Theory of electrostatic interactions in macromolecules
    • Gilson, M. K. Theory of electrostatic interactions in macromolecules Curr. Opin. Struct. Biol. 1995, 5, 216-223
    • (1995) Curr. Opin. Struct. Biol. , vol.5 , pp. 216-223
    • Gilson, M.K.1
  • 40
    • 0034811498 scopus 로고    scopus 로고
    • Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA
    • Wang, J.; Morin, P.; Wang, W.; Kollman, P. A. Use of MM-PBSA in reproducing the binding free energies to HIV-1 RT of TIBO derivatives and predicting the binding mode to HIV-1 RT of efavirenz by docking and MM-PBSA J. Am. Chem. Soc. 2001, 123, 5221-5230
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5221-5230
    • Wang, J.1    Morin, P.2    Wang, W.3    Kollman, P.A.4
  • 41
    • 0035910029 scopus 로고    scopus 로고
    • Computational study of protein specificity: The molecular basis of HIV-1 protease drug resistance
    • Wang, W.; Kollman, P. A. Computational study of protein specificity: the molecular basis of HIV-1 protease drug resistance Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14937-14942
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 14937-14942
    • Wang, W.1    Kollman, P.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.