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Volumn 82, Issue , 2014, Pages 600-611

Design and synthesis of a new series of modified CH-diarylpyrimidines as drug-resistant HIV non-nucleoside reverse transcriptase inhibitors

Author keywords

Cyanide group; Diarylpyrimidines; Docking analysis; Double mutant HIV 1; Non nucleoside HIV RT inhibitors; SAR

Indexed keywords

2 (4 CYANOPHENYLAMINO) 4 (2 CHLOROPHENYL 2 HYDROXYPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CHLOROPHENYLETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CHLOROPHENYLISOPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CHLOROPHENYLMETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CHLOROPHENYLPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLHYDRAZONOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLHYDROXYMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLISOPORPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLMETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (2 CYANOVINYLPHENYLPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYL 2 HYDROXYPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLHYDRAZONOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLHYDROXYMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLISOPROPYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLMETHYLAMINOMETHYL)PYRIMIDINE; 2 (4 CYANOPHENYLAMINO) 4 (4 CYANOPHENYLPROPYLAMINOMETHYL)PYRIMIDINE; DELAVIRDINE; EFAVIRENZ; LAMIVUDINE; NEVIRAPINE; NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PYRIMIDINE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR;

EID: 84903198682     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.059     Document Type: Article
Times cited : (29)

References (49)
  • 1
    • 73549115378 scopus 로고    scopus 로고
    • Non-nucleoside reverse transcriptase inhibitors (NNRTIs), their discovery, development, and use in the treatment of HIV-1 infection: A review of the last 20 years (1989-2009)
    • M.-P. de Béthune Non-nucleoside reverse transcriptase inhibitors (NNRTIs), their discovery, development, and use in the treatment of HIV-1 infection: a review of the last 20 years (1989-2009) Antivir. Res. 85 2010 75 90
    • (2010) Antivir. Res. , vol.85 , pp. 75-90
    • De Béthune, M.-P.1
  • 2
    • 84862580827 scopus 로고    scopus 로고
    • In search of a treatment for HIV-current therapies and the role of non-nucleoside reverse transcriptase inhibitors (NNRTIs)
    • C. Reynolds, C.B. de Koning, S.C. Pelly, W.A. van Otterlo, and M.L. Bode In search of a treatment for HIV-current therapies and the role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) Chem. Soc. Rev. 41 2012 4657 4670
    • (2012) Chem. Soc. Rev. , vol.41 , pp. 4657-4670
    • Reynolds, C.1    De Koning, C.B.2    Pelly, S.C.3    Van Otterlo, W.A.4    Bode, M.L.5
  • 3
    • 0032437454 scopus 로고    scopus 로고
    • The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection
    • E. De Clercq The role of non-nucleoside reverse transcriptase inhibitors (NNRTIs) in the therapy of HIV-1 infection Antivir. Res. 38 1998 153 179
    • (1998) Antivir. Res. , vol.38 , pp. 153-179
    • De Clercq, E.1
  • 4
    • 84876852661 scopus 로고    scopus 로고
    • HIV-1 NNRTIs: Structural diversity, pharmacophore similarity, and implications for drug design
    • P. Zhan, X. Chen, D. Li, Z. Fang, E. De Clercq, and X. Liu HIV-1 NNRTIs: structural diversity, pharmacophore similarity, and implications for drug design Med. Res. Rev. 33 2011 E1 E72
    • (2011) Med. Res. Rev. , vol.33
    • Zhan, P.1    Chen, X.2    Li, D.3    Fang, Z.4    De Clercq, E.5    Liu, X.6
  • 5
    • 1542471588 scopus 로고    scopus 로고
    • Nonnucleoside HIV-1 reverse transcriptase inhibitors: Part I. Synthesis and structure-activity relationship of 1-alkoxymethyl-5-alkyl-6-naphthylmethyl uracils as HEPT analogues
    • G. Meng, F. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Nonnucleoside HIV-1 reverse transcriptase inhibitors: part I. synthesis and structure-activity relationship of 1-alkoxymethyl-5-alkyl-6-naphthylmethyl uracils as HEPT analogues Chem. Pharm. Bull. (Tokyo) 51 2003 779 789
    • (2003) Chem. Pharm. Bull. (Tokyo) , vol.51 , pp. 779-789
    • Meng, G.1    Chen, F.2    De Clercq, E.3    Balzarini, J.4    Pannecouque, C.5
  • 7
    • 60549105209 scopus 로고    scopus 로고
    • Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors
    • Y.-P. Wang, F.-E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Synthesis and in vitro anti-HIV evaluation of a new series of 6-arylmethyl-substituted S-DABOs as potential non-nucleoside HIV-1 reverse transcriptase inhibitors Eur. J. Med. Chem. 44 2009 1016 1023
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 1016-1023
    • Wang, Y.-P.1    Chen, F.-E.2    De Clercq, E.3    Balzarini, J.4    Pannecouque, C.5
  • 8
    • 2442610540 scopus 로고    scopus 로고
    • 5-Alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series
    • Y. He, F. Chen, G. Sun, Y. Wang, E. De Clercq, J. Balzarini, and C. Pannecouque 5-Alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1- naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series Bioorg. Med. Chem. Lett. 14 2004 3173 3176
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 3173-3176
    • He, Y.1    Chen, F.2    Sun, G.3    Wang, Y.4    De Clercq, E.5    Balzarini, J.6    Pannecouque, C.7
  • 10
    • 80051594199 scopus 로고    scopus 로고
    • Revealing the drug-resistant mechanism for diarylpyrimidine analogue inhibitors of HIV-1 reverse transcriptase
    • H. Zhang, F. Qin, W. Ye, Z. Li, S. Ma, Y. Xia, Y. Jiang, J. Zhu, Y. Li, and J. Zhang Revealing the drug-resistant mechanism for diarylpyrimidine analogue inhibitors of HIV-1 reverse transcriptase Chem. Biol. Drug Des. 78 2011 427 437
    • (2011) Chem. Biol. Drug Des. , vol.78 , pp. 427-437
    • Zhang, H.1    Qin, F.2    Ye, W.3    Li, Z.4    Ma, S.5    Xia, Y.6    Jiang, Y.7    Zhu, J.8    Li, Y.9    Zhang, J.10
  • 11
    • 84878004314 scopus 로고    scopus 로고
    • Molecular design, synthesis and biological evaluation of BP-O-DAPY and O-DAPY derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors
    • S.-Q. Yang, C. Pannecouque, D. Daelemans, X.-D. Ma, Y. Liu, F.-E. Chen, and E. De Clercq Molecular design, synthesis and biological evaluation of BP-O-DAPY and O-DAPY derivatives as non-nucleoside HIV-1 reverse transcriptase inhibitors Eur. J. Med. Chem. 65C 2013 134 143
    • (2013) Eur. J. Med. Chem. , vol.65 C , pp. 134-143
    • Yang, S.-Q.1    Pannecouque, C.2    Daelemans, D.3    Ma, X.-D.4    Liu, Y.5    Chen, F.-E.6    De Clercq, E.7
  • 12
    • 12144265244 scopus 로고    scopus 로고
    • Non-nucleoside reverse transcriptase inhibitors (NNRTIs): Past, present, and future
    • E. De Clercq Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future Chem. Biodivers. 1 2004 44 64
    • (2004) Chem. Biodivers. , vol.1 , pp. 44-64
    • De Clercq, E.1
  • 16
    • 0027278282 scopus 로고
    • Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: Structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3-[(1- methylethyl)amino]-pyridinyl]piperazine monomethanesulfonate (U-90152S), a second generation clinical candidate
    • D.L. Romero, R.A. Morge, M.J. Genin, C. Biles, M. Busso, L. Resnick, I.W. Althaus, F. Reusser, R.C. Thomas, and W.G. Tarpley Bis(heteroaryl)piperazine (BHAP) reverse transcriptase inhibitors: structure-activity relationships of novel substituted indole analogues and the identification of 1-[(5-methanesulfonamido-1H-indol-2-yl)-carbonyl]-4-[3-[(1-methylethyl)amino] -pyridinyl]piperazine monomethanesulfonate (U-90152S), a second generation clinical candidate J. Med. Chem. 36 1993 1505 1508
    • (1993) J. Med. Chem. , vol.36 , pp. 1505-1508
    • Romero, D.L.1    Morge, R.A.2    Genin, M.J.3    Biles, C.4    Busso, M.5    Resnick, L.6    Althaus, I.W.7    Reusser, F.8    Thomas, R.C.9    Tarpley, W.G.10
  • 17
    • 77649163883 scopus 로고    scopus 로고
    • IDX-899, an aryl phosphinate-indole non-nucleoside reverse transcriptase inhibitor for the potential treatment of HIV infection
    • O.M. Klibanov, and R.L. Kaczor IDX-899, an aryl phosphinate-indole non-nucleoside reverse transcriptase inhibitor for the potential treatment of HIV infection Curr. Opin. Investig. Drugs 11 2010 237 245
    • (2010) Curr. Opin. Investig. Drugs , vol.11 , pp. 237-245
    • Klibanov, O.M.1    Kaczor, R.L.2
  • 21
    • 50849108264 scopus 로고    scopus 로고
    • Shifting paradigms: The resistance profile of etravirine
    • A.M. Geretti Shifting paradigms: the resistance profile of etravirine J. Antimicrob. Chemother. 62 2008 643 647
    • (2008) J. Antimicrob. Chemother. , vol.62 , pp. 643-647
    • Geretti, A.M.1
  • 22
    • 79251472419 scopus 로고    scopus 로고
    • Recent advances in DAPYs and related analogues as HIV-1 NNRTIs
    • X. Chen, P. Zhan, D. Li, E. De Clercq, and X. Liu Recent advances in DAPYs and related analogues as HIV-1 NNRTIs Curr. Med. Chem. 18 2011 359 376
    • (2011) Curr. Med. Chem. , vol.18 , pp. 359-376
    • Chen, X.1    Zhan, P.2    Li, D.3    De Clercq, E.4    Liu, X.5
  • 25
    • 40349091258 scopus 로고    scopus 로고
    • High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: Strategic flexibility explains potency against resistance mutations
    • K. Das, J.D. Bauman, A.D. Clark, Y.V. Frenkel, P.J. Lewi, A.J. Shatkin, S.H. Hughes, and E. Arnold High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations Proc. Natl. Acad. Sci. U. S. A. 105 2008 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
  • 27
    • 77952724079 scopus 로고    scopus 로고
    • Crystal structures of HIV-1 reverse transcriptase with etravirine (TMC125) and rilpivirine (TMC278): Implications for drug design
    • E.B. Lansdon, K.M. Brendza, M. Hung, R. Wang, S. Mukund, D. Jin, G. Birkus, N. Kutty, and X. Liu Crystal structures of HIV-1 reverse transcriptase with etravirine (TMC125) and rilpivirine (TMC278): implications for drug design J. Med. Chem. 53 2010 4295 4299
    • (2010) J. Med. Chem. , vol.53 , pp. 4295-4299
    • Lansdon, E.B.1    Brendza, K.M.2    Hung, M.3    Wang, R.4    Mukund, S.5    Jin, D.6    Birkus, G.7    Kutty, N.8    Liu, X.9
  • 28
    • 79952608410 scopus 로고    scopus 로고
    • Rational approaches for the design of effective human immunodeficiency virus type 1 nonnucleoside reverse transcriptase inhibitors
    • S.R. Ribone, M.A. Quevedo, M. Madrid, and M.C. BrinoÍn Rational approaches for the design of effective human immunodeficiency virus type 1 nonnucleoside reverse transcriptase inhibitors J. Chem. Inf. Model. 51 2010 130 138
    • (2010) J. Chem. Inf. Model. , vol.51 , pp. 130-138
    • Ribone, S.R.1    Quevedo, M.A.2    Madrid, M.3    Brinoín, M.C.4
  • 29
    • 78649854734 scopus 로고    scopus 로고
    • Design, synthesis, and evaluation of diarylpyridines and diarylanilines as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
    • X. Tian, B. Qin, Z. Wu, X. Wang, H. Lu, S.L. Morris-Natschke, C.H. Chen, S. Jiang, K.-H. Lee, and L. Xie Design, synthesis, and evaluation of diarylpyridines and diarylanilines as potent non-nucleoside HIV-1 reverse transcriptase inhibitors J. Med. Chem. 53 2010 8287 8297
    • (2010) J. Med. Chem. , vol.53 , pp. 8287-8297
    • Tian, X.1    Qin, B.2    Wu, Z.3    Wang, X.4    Lu, H.5    Morris-Natschke, S.L.6    Chen, C.H.7    Jiang, S.8    Lee, K.-H.9    Xie, L.10
  • 32
    • 77950037962 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 4-(hydroxyimino) arylmethyl diarylpyrimidine analogues as potential non-nucleoside reverse transcriptase inhibitors against HIV
    • X.-Q. Feng, Z.-S. Zeng, Y.-H. Liang, F.-E. Chen, C. Pannecouque, J. Balzarini, and E. De Clercq Synthesis and biological evaluation of 4-(hydroxyimino) arylmethyl diarylpyrimidine analogues as potential non-nucleoside reverse transcriptase inhibitors against HIV Bioorg. Med. Chem. 18 2010 2370 2374
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2370-2374
    • Feng, X.-Q.1    Zeng, Z.-S.2    Liang, Y.-H.3    Chen, F.-E.4    Pannecouque, C.5    Balzarini, J.6    De Clercq, E.7
  • 35
    • 82955165647 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of aryl-2-[(4-cyanophenyl) amino]-4-pyrimidinone hydrazones as potent non-nucleoside reverse transcriptase inhibitors
    • X.-D. Ma, S.-Q. Yang, S.-X. Gu, Q.-Q. He, F.-E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Synthesis and anti-HIV activity of aryl-2-[(4-cyanophenyl) amino]-4-pyrimidinone hydrazones as potent non-nucleoside reverse transcriptase inhibitors ChemMedChem 6 2011 2225 2232
    • (2011) ChemMedChem , vol.6 , pp. 2225-2232
    • Ma, X.-D.1    Yang, S.-Q.2    Gu, S.-X.3    He, Q.-Q.4    Chen, F.-E.5    De Clercq, E.6    Balzarini, J.7    Pannecouque, C.8
  • 36
    • 84861632263 scopus 로고    scopus 로고
    • Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors
    • S.-X. Gu, Z.-M. Li, X.-D. Ma, S.-Q. Yang, Q.-Q. He, F.-E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Chiral resolution, absolute configuration assignment and biological activity of racemic diarylpyrimidine CH(OH)-DAPY as potent nonnucleoside HIV-1 reverse transcriptase inhibitors Eur. J. Med. Chem. 53 2012 229 234
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 229-234
    • Gu, S.-X.1    Li, Z.-M.2    Ma, X.-D.3    Yang, S.-Q.4    He, Q.-Q.5    Chen, F.-E.6    De Clercq, E.7    Balzarini, J.8    Pannecouque, C.9
  • 37
    • 84860390578 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship of novel diarylpyrimidines with hydromethyl linker (CH(OH)-DAPYs) as HIV-1 NNRTIs
    • S.-X. Gu, Q.-Q. He, S.-Q. Yang, X.-D. Ma, F.-E. Chen, E. De Clercq, J. Balzarini, and C. Pannecouque Synthesis and structure-activity relationship of novel diarylpyrimidines with hydromethyl linker (CH(OH)-DAPYs) as HIV-1 NNRTIs Bioorg. Med. Chem. 19 2011 5117 5124
    • (2011) Bioorg. Med. Chem. , vol.19 , pp. 5117-5124
    • Gu, S.-X.1    He, Q.-Q.2    Yang, S.-Q.3    Ma, X.-D.4    Chen, F.-E.5    De Clercq, E.6    Balzarini, J.7    Pannecouque, C.8
  • 40
    • 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
    • K. Das, P.J. Lewi, S.H. Hughes, and E. Arnold 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 2005 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
  • 41
    • 20144368570 scopus 로고    scopus 로고
    • Structure-based design, parallel synthesis, structure-activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives
    • A. Ranise, A. Spallarossa, S. Cesarini, F. Bondavalli, S. Schenone, O. Bruno, G. Menozzi, P. Fossa, L. Mosti, and M. La Colla Structure-based design, parallel synthesis, structure-activity relationship, and molecular modeling studies of thiocarbamates, new potent non-nucleoside HIV-1 reverse transcriptase inhibitor isosteres of phenethylthiazolylthiourea derivatives J. Med. Chem. 48 2005 3858 3873
    • (2005) J. Med. Chem. , vol.48 , pp. 3858-3873
    • Ranise, A.1    Spallarossa, A.2    Cesarini, S.3    Bondavalli, F.4    Schenone, S.5    Bruno, O.6    Menozzi, G.7    Fossa, P.8    Mosti, L.9    La Colla, M.10
  • 42
    • 40749129190 scopus 로고    scopus 로고
    • Tetrazolium-based colorimetric assay for the detection of HIV replication inhibitors: Revisited 20 years later
    • C. Pannecouque, D. Daelemans, and E. De Clercq Tetrazolium-based colorimetric assay for the detection of HIV replication inhibitors: revisited 20 years later Nat. Protoc. 3 2008 427 434
    • (2008) Nat. Protoc. , vol.3 , pp. 427-434
    • Pannecouque, C.1    Daelemans, D.2    De Clercq, E.3
  • 44
    • 0036156328 scopus 로고    scopus 로고
    • Chimeric human immunodeficiency virus type 1 and feline immunodeficiency virus reverse transcriptases: Role of the subunits in resistance/sensitivity to non-nucleoside reverse transcriptase inhibitors
    • J. Auwerx, T.W. North, B.D. Preston, G.J. Klarmann, E. De Clercq, and J. Balzarini Chimeric human immunodeficiency virus type 1 and feline immunodeficiency virus reverse transcriptases: role of the subunits in resistance/sensitivity to non-nucleoside reverse transcriptase inhibitors Mol. Pharmacol. 61 2002 400 406
    • (2002) Mol. Pharmacol. , vol.61 , pp. 400-406
    • Auwerx, J.1    North, T.W.2    Preston, B.D.3    Klarmann, G.J.4    De Clercq, E.5    Balzarini, J.6
  • 45
    • 0031194671 scopus 로고    scopus 로고
    • Characterization of PicoGreen reagent and development of a fluorescence-based solution assay for double-stranded DNA quantitation
    • V.L. Singer, L.J. Jones, S.T. Yue, and R.P. Haugland Characterization of PicoGreen reagent and development of a fluorescence-based solution assay for double-stranded DNA quantitation Anal. Biochem. 249 1997 228 238
    • (1997) Anal. Biochem. , vol.249 , pp. 228-238
    • Singer, V.L.1    Jones, L.J.2    Yue, S.T.3    Haugland, R.P.4
  • 46
    • 84865214371 scopus 로고    scopus 로고
    • Surflex-Dock: Docking benchmarks and real-world application
    • R. Spitzer, and A.N. Jain Surflex-Dock: docking benchmarks and real-world application J. Comput. Aided Mol. Des. 26 2012 687 699
    • (2012) J. Comput. Aided Mol. Des. , vol.26 , pp. 687-699
    • Spitzer, R.1    Jain, A.N.2
  • 47
    • 34247343346 scopus 로고    scopus 로고
    • Surflex-Dock 2.1: Robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search
    • A.N. Jain Surflex-Dock 2.1: robust performance from ligand energetic modeling, ring flexibility, and knowledge-based search J. Comput. Aided Mol. Des. 21 2007 281 306
    • (2007) J. Comput. Aided Mol. Des. , vol.21 , pp. 281-306
    • Jain, A.N.1
  • 48
    • 0037434582 scopus 로고    scopus 로고
    • Surflex: Fully automatic flexible molecular docking using a molecular similarity-based search engine
    • A.N. Jain Surflex: fully automatic flexible molecular docking using a molecular similarity-based search engine J. Med. Chem. 46 2003 499 511
    • (2003) J. Med. Chem. , vol.46 , pp. 499-511
    • Jain, A.N.1
  • 49
    • 0030979125 scopus 로고    scopus 로고
    • Automatic identification and representation of protein binding sites for molecular docking
    • J. Ruppert, W. Welch, and A.N. Jain Automatic identification and representation of protein binding sites for molecular docking Protein Sci. 6 1997 524 533
    • (1997) Protein Sci. , vol.6 , pp. 524-533
    • Ruppert, J.1    Welch, W.2    Jain, A.N.3


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