메뉴 건너뛰기




Volumn 51, Issue 15, 2008, Pages 4641-4652

5-alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones, a series of anti-HIV-1 agents of the dihydro-alkoxy-benzyl-oxopyrimidine family with peculiar structure - Activity relationship profile

Author keywords

[No Author keywords available]

Indexed keywords

ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; PYRIMIDINE DERIVATIVE;

EID: 49449113636     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800340w     Document Type: Article
Times cited : (57)

References (59)
  • 1
    • 84885332080 scopus 로고    scopus 로고
    • Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): The DABOs family
    • Artico, M. Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drug Future 2002, 27, 159-175.
    • (2002) Drug Future , vol.27 , pp. 159-175
    • Artico, M.1
  • 2
    • 0842279477 scopus 로고    scopus 로고
    • 3,4-Dihydro-2-alkoxy-6-benzyl-oxopyrimidines (DABOs): Development of a potent class of non-nucleoside reverse transcriptase inhibitors
    • Marongiu, M. E.; Pani, A.; Musiu, C.; La Colla, P.; Mai, A.; Sbardella, G.; Massa, S.; Artico, M. 3,4-Dihydro-2-alkoxy-6-benzyl-oxopyrimidines (DABOs): Development of a potent class of non-nucleoside reverse transcriptase inhibitors. Recent Res. Dev. Med. Chem. 2001, 1, 65-92.
    • (2001) Recent Res. Dev. Med. Chem , vol.1 , pp. 65-92
    • Marongiu, M.E.1    Pani, A.2    Musiu, C.3    La Colla, P.4    Mai, A.5    Sbardella, G.6    Massa, S.7    Artico, M.8
  • 4
    • 14944344464 scopus 로고    scopus 로고
    • De Clercq, E. New Approaches toward Anti-HIV Chemotherapy. J. Med. Chem. 2005, 48, 1297-1313.
    • De Clercq, E. New Approaches toward Anti-HIV Chemotherapy. J. Med. Chem. 2005, 48, 1297-1313.
  • 6
    • 0026691450 scopus 로고    scopus 로고
    • Botta, M.; Artico, M.; Massa, S.; Gambacorta, A.; Marongiu, M. E.; Pani, A.; La Colla, P. Synthesis, Antimicrobial and Antiviral Activities of Isotrimethoprim and Some Related Derivatives. Eur. J. Med. Chem. 1992, 27, 251-257.
    • Botta, M.; Artico, M.; Massa, S.; Gambacorta, A.; Marongiu, M. E.; Pani, A.; La Colla, P. Synthesis, Antimicrobial and Antiviral Activities of Isotrimethoprim and Some Related Derivatives. Eur. J. Med. Chem. 1992, 27, 251-257.
  • 7
    • 0027521797 scopus 로고
    • 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs): A New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1
    • Artico, M.; Massa, S.; Mai, A.; Marongiu, M. E.; Piras, G.; Tramontano, E.; La Colla, P. 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs): a New Class of Specific Inhibitors of Human Immunodeficiency Virus Type 1. Antiviral Chem. Chemother. 1993, 4, 361-368.
    • (1993) Antiviral Chem. Chemother , vol.4 , pp. 361-368
    • Artico, M.1    Massa, S.2    Mai, A.3    Marongiu, M.E.4    Piras, G.5    Tramontano, E.6    La Colla, P.7
  • 8
    • 0028522917 scopus 로고
    • Characterization of the Anti-HIV-1 Activity of 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), New Non-Nucleoside Reverse Transcriptase Inhibitors
    • Tramontano, E.; Marongiu, M. E.; De Montis, A.; Loi, A. G.; Artico, M.; Massa, S.; Mai, A.; La Colla, P. Characterization of the Anti-HIV-1 Activity of 3,4-Dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), New Non-Nucleoside Reverse Transcriptase Inhibitors. Microbiologica 1994, 17, 269-279.
    • (1994) Microbiologica , vol.17 , pp. 269-279
    • Tramontano, E.1    Marongiu, M.E.2    De Montis, A.3    Loi, A.G.4    Artico, M.5    Massa, S.6    Mai, A.7    La Colla, P.8
  • 9
    • 0028869436 scopus 로고
    • Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus Type-1
    • Massa, S.; Mai, A.; Artico, M.; Sbardella, G.; Tramontano, E.; Loi, A. G.; Scano, P.; La Colla, P. Synthesis and antiviral activity of new 3,4-dihydro-2-alkoxy-6-benzyl-4-oxopyrimidines (DABOs), specific inhibitors of human immunodeficiency virus Type-1. Antiviral Chem. Chemother. 1995, 6, 1-8.
    • (1995) Antiviral Chem. Chemother , vol.6 , pp. 1-8
    • Massa, S.1    Mai, A.2    Artico, M.3    Sbardella, G.4    Tramontano, E.5    Loi, A.G.6    Scano, P.7    La Colla, P.8
  • 11
    • 0030213813 scopus 로고    scopus 로고
    • Ettorre, A.; Mai, A.; Artico, M.; Massa, S.; De Montis, A.; La Colla, P. 6-(3-Methylbenzyl)-2-(2-methylpropyl)thio-4(3H)-pyrimidinone (DABO 622). Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1996, 52, 2115-2117.
    • Ettorre, A.; Mai, A.; Artico, M.; Massa, S.; De Montis, A.; La Colla, P. 6-(3-Methylbenzyl)-2-(2-methylpropyl)thio-4(3H)-pyrimidinone (DABO 622). Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1996, 52, 2115-2117.
  • 13
    • 0033602141 scopus 로고    scopus 로고
    • Mai, A.; Artico, M.; Sbardella, G.; Massa, S.; Novellino, E.; Greco, G.; Loi, A. G.; Tramontano, E.; Marongiu, M. E.; La Colla, P. 5-Alkyl-2-(alkylthio)- 6-(2,6-dihalophenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones: Novel Potent and Selective Dihydro-alkoxy-benzyl-oxopyrimidine Derivatives. J. Med. Chem. 1999, 42, 619-627.
    • Mai, A.; Artico, M.; Sbardella, G.; Massa, S.; Novellino, E.; Greco, G.; Loi, A. G.; Tramontano, E.; Marongiu, M. E.; La Colla, P. 5-Alkyl-2-(alkylthio)- 6-(2,6-dihalophenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones: Novel Potent and Selective Dihydro-alkoxy-benzyl-oxopyrimidine Derivatives. J. Med. Chem. 1999, 42, 619-627.
  • 15
    • 0034975054 scopus 로고    scopus 로고
    • Structure-activity relationship studies on new DABOs: Effect of substitutions at pyrimidine C-5 and C-6 positions on anti-HIV-1 activity
    • Sbardella, G.; Mai, A.; Artico, M.; Chimenti, P.; Massa, S.; Loddo, R.; Marongiu, M. E.; La Colla, P.; Pani, A. Structure-activity relationship studies on new DABOs: effect of substitutions at pyrimidine C-5 and C-6 positions on anti-HIV-1 activity. Antiviral Chem. Chemother. 2001, 12, 37-50.
    • (2001) Antiviral Chem. Chemother , vol.12 , pp. 37-50
    • Sbardella, G.1    Mai, A.2    Artico, M.3    Chimenti, P.4    Massa, S.5    Loddo, R.6    Marongiu, M.E.7    La Colla, P.8    Pani, A.9
  • 17
    • 0035797356 scopus 로고    scopus 로고
    • Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Novellino, E.; Greco, G.; Lavecchia, A.; Musiu, C.; La Colla, M.; Murgioni, C.; La Colla, P.; Loddo, R. Structure-based Design, Synthesis, and Biological Evaluation of Conformationally Restricted Novel 2-Alkylthio-6-[1-(2,6-difluorophenyl)alkyl]-3, 4-dihydro-5-alkylpyrimidin-4(3H)-ones as Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase. J. Med. Chem. 2001, 44, 2544-2554.
    • Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Novellino, E.; Greco, G.; Lavecchia, A.; Musiu, C.; La Colla, M.; Murgioni, C.; La Colla, P.; Loddo, R. Structure-based Design, Synthesis, and Biological Evaluation of Conformationally Restricted Novel 2-Alkylthio-6-[1-(2,6-difluorophenyl)alkyl]-3, 4-dihydro-5-alkylpyrimidin-4(3H)-ones as Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase. J. Med. Chem. 2001, 44, 2544-2554.
  • 18
    • 0035146092 scopus 로고    scopus 로고
    • Quaglia, M. G.; Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Del Piano, D.; Setzu, G.; Doratiotto, S.; Cotichini, V. Chiral Resolution and Molecular Modeling Investigation of rac-2-Cyclopentylthio-6-[1-(2,6- difluorophenyl)ethyl]-3,4-dihydro-5-methylpyrimidin-4(3H)-one (MC-1047), a Potent Anti-HIV-1 Reverse Transcriptase Agent of the DABO Class. Chirality 2001, 13, 75-80.
    • Quaglia, M. G.; Mai, A.; Sbardella, G.; Artico, M.; Ragno, R.; Massa, S.; Del Piano, D.; Setzu, G.; Doratiotto, S.; Cotichini, V. Chiral Resolution and Molecular Modeling Investigation of rac-2-Cyclopentylthio-6-[1-(2,6- difluorophenyl)ethyl]-3,4-dihydro-5-methylpyrimidin-4(3H)-one (MC-1047), a Potent Anti-HIV-1 Reverse Transcriptase Agent of the DABO Class. Chirality 2001, 13, 75-80.
  • 19
    • 10744230514 scopus 로고    scopus 로고
    • Ragno, R.; Mai, A.; Sbardella, S.; Artico, M.; Massa, S.; Musiu, C.; Mura, M.; Marceddu, T.; Cadeddu, A.; La Colla, P. Computer-aided design, synthesis, and anti-HIV-1 activity in vitro of 2-alkylamino-6-[1-(2,6- difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as novel potent non-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant. J. Med. Chem. 2004, 47, 928-934.
    • Ragno, R.; Mai, A.; Sbardella, S.; Artico, M.; Massa, S.; Musiu, C.; Mura, M.; Marceddu, T.; Cadeddu, A.; La Colla, P. Computer-aided design, synthesis, and anti-HIV-1 activity in vitro of 2-alkylamino-6-[1-(2,6- difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as novel potent non-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant. J. Med. Chem. 2004, 47, 928-934.
  • 20
    • 13844316071 scopus 로고    scopus 로고
    • 5-Alkyl-2-alkylamino-6-(2,6-difluorophenylalkyl)-3,4-dihydropyrimidin-4(3 H)-ones, a new series of potent, broad-spectrum non-nucleoside reverse transcriptase inhibitors belonging to the DABO family
    • Mai, A.; Artico, M.; Ragno, R.; Sbardella, G.; Massa, S.; Musiu, C.; Mura, M.; Marturana, F.; Cadeddu, A.; Maga, G.; La Colla, P. 5-Alkyl-2-alkylamino-6-(2,6-difluorophenylalkyl)-3,4-dihydropyrimidin-4(3 H)-ones, a new series of potent, broad-spectrum non-nucleoside reverse transcriptase inhibitors belonging to the DABO family. Bioorg. Med. Chem. 2005, 13, 2065-2077.
    • (2005) Bioorg. Med. Chem , vol.13 , pp. 2065-2077
    • Mai, A.1    Artico, M.2    Ragno, R.3    Sbardella, G.4    Massa, S.5    Musiu, C.6    Mura, M.7    Marturana, F.8    Cadeddu, A.9    Maga, G.10    La Colla, P.11
  • 22
    • 35848949355 scopus 로고    scopus 로고
    • Mai, A.; Artico, M.; Rotili, D.; Tarantino, D.; Clotet-Codina, I.; Armand-Ugón, M.; Ragno, R.; Simeoni, S.; Sbardella, G.; Nawrozkij, M. B.; Samuele, A.; Maga, G.; Esté, J. A. Synthesis and Biological Properties of Novel 2-Aminopyrimidin-4(3H)-ones Highly Potent Against HIV-1 Mutant Strains. J. Med. Chem. 2007, 50, 5412-5424.
    • Mai, A.; Artico, M.; Rotili, D.; Tarantino, D.; Clotet-Codina, I.; Armand-Ugón, M.; Ragno, R.; Simeoni, S.; Sbardella, G.; Nawrozkij, M. B.; Samuele, A.; Maga, G.; Esté, J. A. Synthesis and Biological Properties of Novel 2-Aminopyrimidin-4(3H)-ones Highly Potent Against HIV-1 Mutant Strains. J. Med. Chem. 2007, 50, 5412-5424.
  • 24
    • 0024408374 scopus 로고
    • A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine
    • Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R. T.; Balzarini, J.; De Clercq, E. A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1989, 32, 2507-2509.
    • (1989) J. Med. Chem , vol.32 , pp. 2507-2509
    • Miyasaka, T.1    Tanaka, H.2    Baba, M.3    Hayakawa, H.4    Walker, R.T.5    Balzarini, J.6    De Clercq, E.7
  • 25
    • 0027436898 scopus 로고
    • Selective and synergistic inhibition of human immunodeficiency virus type 1 reverse transcriptase by a non-nucleoside inhibitor, MKC-442
    • Yuasa, S.; Sadakata, Y.; Takashima, H.; Sekiya, K.; Inouye, N.; Ubasawa, M.; Baba, M. Selective and synergistic inhibition of human immunodeficiency virus type 1 reverse transcriptase by a non-nucleoside inhibitor, MKC-442. Mol. Pharmacol. 1993, 44, 895-900.
    • (1993) Mol. Pharmacol , vol.44 , pp. 895-900
    • Yuasa, S.1    Sadakata, Y.2    Takashima, H.3    Sekiya, K.4    Inouye, N.5    Ubasawa, M.6    Baba, M.7
  • 27
    • 0029096567 scopus 로고
    • Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) as potent and selective anti-HIV-1 agents
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) as potent and selective anti-HIV-1 agents. J. Med. Chem. 1995, 38, 2860-2865.
    • (1995) J. Med. Chem , vol.38 , pp. 2860-2865
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Inouye, N.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 28
    • 0033524008 scopus 로고    scopus 로고
    • Design of MKC-442 (emivirine) analogues with improved activity against drug-resistant HIV mutants
    • Hopkins, A. L.; Ren, J.; Tanaka, H.; Baba, M.; Okamato, M.; Stuart, D. I.; Stammers, D. K. Design of MKC-442 (emivirine) analogues with improved activity against drug-resistant HIV mutants. J. Med. Chem. 1999, 42, 4500-4505.
    • (1999) J. Med. Chem , vol.42 , pp. 4500-4505
    • Hopkins, A.L.1    Ren, J.2    Tanaka, H.3    Baba, M.4    Okamato, M.5    Stuart, D.I.6    Stammers, D.K.7
  • 29
    • 49449115042 scopus 로고    scopus 로고
    • 13 The physical and chemical data for compounds 1a-p have been reported in Table S1 as Supporting Information. Compounds 1q,r, here reported for a direct comparison as reference drugs, were described in ref 13.
    • 13 The physical and chemical data for compounds 1a-p have been reported in Table S1 as Supporting Information. Compounds 1q,r, here reported for a direct comparison as reference drugs, were described in ref 13.
  • 32
    • 37349004798 scopus 로고    scopus 로고
    • Mugnaini, C.; Alongi, M.; Togninelli, A.; Gevarija, H.; Brizzi, A.; Manetti, F.; Bernardini, C.; Angeli, L.; Tafi, A.; Bellucci, L.; Corelli, F.; Massa, S.; Maga, G.; Samuele, A.; Facchini, M.; Clotet-Codina, I.; Armand-Ugón, M.; Esté, J. A.; Botta, M. Dihydro-alkylthio-benzyl- oxopyrimidines as Inhibitors of Reverse Transcriptase: Synthesis and Rationalization of the Biological Data on Both Wild-Type Enzyme and Relevant Clinical Mutants. J. Med. Chem. 2007, 50, 6580-6505.
    • Mugnaini, C.; Alongi, M.; Togninelli, A.; Gevarija, H.; Brizzi, A.; Manetti, F.; Bernardini, C.; Angeli, L.; Tafi, A.; Bellucci, L.; Corelli, F.; Massa, S.; Maga, G.; Samuele, A.; Facchini, M.; Clotet-Codina, I.; Armand-Ugón, M.; Esté, J. A.; Botta, M. Dihydro-alkylthio-benzyl- oxopyrimidines as Inhibitors of Reverse Transcriptase: Synthesis and Rationalization of the Biological Data on Both Wild-Type Enzyme and Relevant Clinical Mutants. J. Med. Chem. 2007, 50, 6580-6505.
  • 33
    • 2442610540 scopus 로고    scopus 로고
    • He, Y.; Chen, F.; Sun, G.; Wang, Y.; De Clercq, E.; Balzarini, J.; Pannecouque, C. 5-Alkyl-2-[(aryl and lakyloxylcarbonylmethyl)thio]-6-(1- naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series. Bioorg. Med. Chem. Lett. 2004, 14, 3173-3176.
    • He, Y.; Chen, F.; Sun, G.; Wang, Y.; De Clercq, E.; Balzarini, J.; Pannecouque, C. 5-Alkyl-2-[(aryl and lakyloxylcarbonylmethyl)thio]-6-(1- naphthylmethyl) pyrimidin-4(3H)-ones as an unique HIV reverse transcriptase inhibitors of S-DABO series. Bioorg. Med. Chem. Lett. 2004, 14, 3173-3176.
  • 34
    • 8644248445 scopus 로고    scopus 로고
    • He, Y.; Chen, F.; Yu, X.; Wang, Y.; De Clercq, E.; Balzarini, J.; Pannecouque, C. Non-nucleoside HIV-1 reverse transcriptase inhibitors; part 3. Synthesis and antiviral activity of 5-alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones. Bioorg. Chem. 2004, 32, 536-548.
    • He, Y.; Chen, F.; Yu, X.; Wang, Y.; De Clercq, E.; Balzarini, J.; Pannecouque, C. Non-nucleoside HIV-1 reverse transcriptase inhibitors; part 3. Synthesis and antiviral activity of 5-alkyl-2-[(aryl and alkyloxylcarbonylmethyl)thio]-6-(1-naphthylmethyl) pyrimidin-4(3H)-ones. Bioorg. Chem. 2004, 32, 536-548.
  • 35
    • 0042089861 scopus 로고
    • Mono-and dialkylation of ethyl dihaloacetates by reaction with organoboranes under the influence of potassium tert-butoxide. Convenient procedures for the conversion of olefins into the alpha-halo alkanoic or dialkylacetic acid esters via hydroboration
    • Brown, H. C.; Rogic, M. M.; Rathke, M. W.; Kabalka, G. W. Mono-and dialkylation of ethyl dihaloacetates by reaction with organoboranes under the influence of potassium tert-butoxide. Convenient procedures for the conversion of olefins into the alpha-halo alkanoic or dialkylacetic acid esters via hydroboration. J. Am. Chem. Soc. 1968, 90, 1911-1913.
    • (1968) J. Am. Chem. Soc , vol.90 , pp. 1911-1913
    • Brown, H.C.1    Rogic, M.M.2    Rathke, M.W.3    Kabalka, G.W.4
  • 36
    • 0029976422 scopus 로고    scopus 로고
    • Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors
    • Hopkins, A. L.; Ren, J.; Esnouf, R. M.; Willcox, B. E.; Jones, E. Y.; Ross, C.; Miyasaka, T.; Walker, R. T.; Tanaka, H.; Stammers, D. K.; Stuart, D. I. Complexes of HIV-1 reverse transcriptase with inhibitors of the HEPT series reveal conformational changes relevant to the design of potent non-nucleoside inhibitors. J. Med. Chem. 1996, 39, 1589-1600.
    • (1996) J. Med. Chem , vol.39 , pp. 1589-1600
    • Hopkins, A.L.1    Ren, J.2    Esnouf, R.M.3    Willcox, B.E.4    Jones, E.Y.5    Ross, C.6    Miyasaka, T.7    Walker, R.T.8    Tanaka, H.9    Stammers, D.K.10    Stuart, D.I.11
  • 38
    • 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
    • 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.
    • (2001) J. Mol. Biol , vol.312 , 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
  • 39
    • 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
    • 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.
    • (2004) J. Mol. Biol , vol.336 , 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
  • 40
    • 0029705324 scopus 로고    scopus 로고
    • Automated docking of flexible ligands: Applications of AutoDock
    • Goodsell, D. S.; Morris, G. M.; Olson, A. J. Automated docking of flexible ligands: applications of AutoDock. J. Mol. Recognit. 1996, 9, 1-5.
    • (1996) J. Mol. Recognit , vol.9 , pp. 1-5
    • Goodsell, D.S.1    Morris, G.M.2    Olson, A.J.3
  • 41
    • 0030935265 scopus 로고    scopus 로고
    • Unique features in the structure of the complex between HIV-1 reverse transcriptase and the bis(heteroaryl)piperazine (BHAP) U-90152 explain resistance mutations for this non-nucleoside inhibitor
    • Esnouf, R. M.; Ren, J.; Hopkins, A. L.; Ross, C. K.; Jones, E. Y.; Stammers, D. K.; Stuart, D. I. Unique features in the structure of the complex between HIV-1 reverse transcriptase and the bis(heteroaryl)piperazine (BHAP) U-90152 explain resistance mutations for this non-nucleoside inhibitor. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3984-3989.
    • (1997) Proc. Natl. Acad. Sci. U.S.A , vol.94 , pp. 3984-3989
    • Esnouf, R.M.1    Ren, J.2    Hopkins, A.L.3    Ross, C.K.4    Jones, E.Y.5    Stammers, D.K.6    Stuart, D.I.7
  • 42
    • 0042706375 scopus 로고    scopus 로고
    • HIV-1 Resistance to the gp41-Dependent Fusion Inhibitor C-34
    • Armand-Ugon, M.; Gutierrez, A.; Clotet, B.; Esté, J. A. HIV-1 Resistance to the gp41-Dependent Fusion Inhibitor C-34. Antiviral Res. 2003, 59, 137-142.
    • (2003) Antiviral Res , vol.59 , pp. 137-142
    • Armand-Ugon, M.1    Gutierrez, A.2    Clotet, B.3    Esté, J.A.4
  • 44
    • 37349119039 scopus 로고    scopus 로고
    • HIV-1 escape to CCR5 coreceptor antagonism through selection of CXCR4-using variants in vitro
    • Moncunill, G.; Armand-Ugon, M.; Pauls, E.; Clotet, B.; Esté, J. A. HIV-1 escape to CCR5 coreceptor antagonism through selection of CXCR4-using variants in vitro. AIDS 2008, 22, 23-31.
    • (2008) AIDS , vol.22 , pp. 23-31
    • Moncunill, G.1    Armand-Ugon, M.2    Pauls, E.3    Clotet, B.4    Esté, J.A.5
  • 45
    • 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
    • Maga, G.; Amacker, M.; Ruel, N.; Hubscher, 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.
    • (1997) J. Mol. Biol , vol.274 , pp. 738-747
    • Maga, G.1    Amacker, M.2    Ruel, N.3    Hubscher, U.4    Spadari, S.5
  • 54
    • 33748276474 scopus 로고    scopus 로고
    • Protein-ligand docking: Current status and future challenges
    • Sousa, S. F.; Fernandes, P. A.; Ramos, M. J. Protein-ligand docking: current status and future challenges. Proteins 2006, 65, 15-26.
    • (2006) Proteins , vol.65 , pp. 15-26
    • Sousa, S.F.1    Fernandes, P.A.2    Ramos, M.J.3
  • 55
    • 33947716119 scopus 로고    scopus 로고
    • A semiempirical free energy force field with charge-based desolvation
    • Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. A semiempirical free energy force field with charge-based desolvation. J. Comput. Chem. 2007, 28, 1145-1152.
    • (2007) J. Comput. Chem , vol.28 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 56
    • 12144278681 scopus 로고    scopus 로고
    • HIV-reverse transcriptase inhibition: Inclusion of ligand-induced fit by cross-docking studies
    • Ragno, R.; Frasca, S.; Manetti, F.; Brizzi, A.; Massa, S. HIV-reverse transcriptase inhibition: inclusion of ligand-induced fit by cross-docking studies. J. Med. Chem. 2005, 48, 200-212.
    • (2005) J. Med. Chem , vol.48 , pp. 200-212
    • Ragno, R.1    Frasca, S.2    Manetti, F.3    Brizzi, A.4    Massa, S.5
  • 57
    • 0002024882 scopus 로고    scopus 로고
    • Krause, S.; Willighagen, E.; Steinbeck, C. J. ChemPaint: Using the Collaborative Forces of the Internet to Develop a Free Editor for 2D Chemical Structures. Molecules 2000, 5, 93-98.
    • Krause, S.; Willighagen, E.; Steinbeck, C. J. ChemPaint: Using the Collaborative Forces of the Internet to Develop a Free Editor for 2D Chemical Structures. Molecules 2000, 5, 93-98.
  • 58
    • 33745135773 scopus 로고    scopus 로고
    • Recent developments of the chemistry development kit (CDK): An open-source Java library for chemo- and bioinformatics
    • Steinbeck, C.; Hoppe, C.; Kuhn, S.; Floris, M.; Guha, R.; Willighagen, E. L. Recent developments of the chemistry development kit (CDK): an open-source Java library for chemo- and bioinformatics. Curr. Pharm. Des. 2006, 12, 2111-2120.
    • (2006) Curr. Pharm. Des , vol.12 , pp. 2111-2120
    • Steinbeck, C.1    Hoppe, C.2    Kuhn, S.3    Floris, M.4    Guha, R.5    Willighagen, E.L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.