메뉴 건너뛰기




Volumn 42, Issue 12, 1998, Pages 3225-3233

Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase

Author keywords

[No Author keywords available]

Indexed keywords

5 ISOPROPYL 2 [(METHYLTHIOMETHYL)THIO] 6 (BENZYL)PYRIMIDIN 4 (1H) ONE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DELAVIRDINE; EMIVIRINE; NEVIRAPINE; PYRIMIDINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0031729622     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.42.12.3225     Document Type: Article
Times cited : (61)

References (49)
  • 3
    • 0029437758 scopus 로고
    • Novel concepts in the treatment of human immunodeficiency virus type 1 (HIV-1) infections by HIV-1-specific reverse transcriptase inhibitors
    • Balzarini, J. 1995. Novel concepts in the treatment of human immunodeficiency virus type 1 (HIV-1) infections by HIV-1-specific reverse transcriptase inhibitors. Verh. K. Acad. Geneeskd. Belg. 57:575-600.
    • (1995) Verh. K. Acad. Geneeskd. Belg. , vol.57 , pp. 575-600
    • Balzarini, J.1
  • 4
    • 0026606044 scopus 로고
    • 2′,5′-Bis-O-(tertbutyldimethylsilyl)-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2′-dioxide) pyrimidine (TSAO) nucleoside analogues: Highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase
    • Balzarini, J., M. J. Perez Perez, A. San Felix, D. Schols, C. F. Perno, A. M. Vandamme, M. J. Camarasa, and E. De Clercq. 1992. 2′,5′-Bis-O-(tertbutyldimethylsilyl)-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2′-dioxide) pyrimidine (TSAO) nucleoside analogues: highly selective inhibitors of human immunodeficiency virus type 1 that are targeted at the viral reverse transcriptase. Proc. Natl. Acad. Sci. USA 89:4392-4396.
    • (1992) Proc. Natl. Acad. Sci. USA , vol.89 , pp. 4392-4396
    • Balzarini, J.1    Perez Perez, M.J.2    San Felix, A.3    Schols, D.4    Perno, C.F.5    Vandamme, A.M.6    Camarasa, M.J.7    De Clercq, E.8
  • 6
    • 0028454828 scopus 로고
    • The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure
    • Bohm, H. J. 1994. The development of a simple empirical scoring function to estimate the binding constant for a protein-ligand complex of known three-dimensional structure. J. Comput.-Aided Mol. Des. 8:243-256.
    • (1994) J. Comput.-Aided Mol. Des. , vol.8 , pp. 243-256
    • Bohm, H.J.1
  • 7
    • 0027027467 scopus 로고
    • LUDI: Rule-based automatic design of new substituents for enzyme inhibitor leads
    • Bohm, H. J. 1992. LUDI: rule-based automatic design of new substituents for enzyme inhibitor leads. J. Comput.-Aided Mol. Des. 6:593-606.
    • (1992) J. Comput.-Aided Mol. Des. , vol.6 , pp. 593-606
    • Bohm, H.J.1
  • 8
    • 0024969084 scopus 로고
    • Scintillation proximity assay
    • Bosworth, N., and P. Towers. 1989. Scintillation proximity assay. Nature 341: 167-168.
    • (1989) Nature , vol.341 , pp. 167-168
    • Bosworth, N.1    Towers, P.2
  • 11
    • 8244226649 scopus 로고    scopus 로고
    • Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates
    • Buckheit, R. W., Jr., M. J. Snow, V. Fliakas-Boltz, T. L. Kinjerski, J. D. Russell, L. A. Pallansch, W. G. Brouwer, and S. S. Yang. 1997. Highly potent oxathiin carboxanilide derivatives with efficacy against nonnucleoside reverse transcriptase inhibitor-resistant human immunodeficiency virus isolates. Antimicrob. Agents Chemother. 41:831-837.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 831-837
    • Buckheit R.W., Jr.1    Snow, M.J.2    Fliakas-Boltz, V.3    Kinjerski, T.L.4    Russell, J.D.5    Pallansch, L.A.6    Brouwer, W.G.7    Yang, S.S.8
  • 13
    • 0021107965 scopus 로고
    • Solvent-accessible surfaces of proteins and nucleic acids
    • Connolly, M. L. 1983. Solvent-accessible surfaces of proteins and nucleic acids. Science 221:709-713.
    • (1983) Science , vol.221 , pp. 709-713
    • Connolly, M.L.1
  • 14
    • 0029939554 scopus 로고    scopus 로고
    • Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine
    • Danel, K., E. Larsen, E. B. Pedersen, B. F. Vestergaard, and C. Nielsen. 1996. Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 39:2427-2431.
    • (1996) J. Med. Chem. , vol.39 , pp. 2427-2431
    • Danel, K.1    Larsen, E.2    Pedersen, E.B.3    Vestergaard, B.F.4    Nielsen, C.5
  • 15
    • 0031086857 scopus 로고    scopus 로고
    • Anti-HIV active naphthyl analogues of HEPT and DABO
    • Danel, K., C. Nielsen, and E. B. Pedersen. 1997. Anti-HIV active naphthyl analogues of HEPT and DABO. Acta Chem. Scand. 51:426-430.
    • (1997) Acta Chem. Scand. , vol.51 , pp. 426-430
    • Danel, K.1    Nielsen, C.2    Pedersen, E.B.3
  • 16
    • 0031942724 scopus 로고    scopus 로고
    • Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones
    • Danel, K., E. B. Pedersen, and C. Nielsen. 1998. Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones. J. Med. Chem. 41:191-198.
    • (1998) J. Med. Chem. , vol.41 , pp. 191-198
    • Danel, K.1    Pedersen, E.B.2    Nielsen, C.3
  • 19
    • 0029011730 scopus 로고
    • Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections
    • De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517.
    • (1995) J. Med. Chem. , vol.38 , pp. 2491-2517
    • De Clercq, E.1
  • 20
    • 0029075207 scopus 로고
    • Structure of HIV-1 RT/TIBO R 86183 complex reveals similarity in the binding of diverse nonnucleoside inhibitors
    • Ding, J., K. Das, H. Moereels, L. Koymans, K. Andries, P. A. Janssen, S. H. Hughes, and E. Arnold. 1995. Structure of HIV-1 RT/TIBO R 86183 complex reveals similarity in the binding of diverse nonnucleoside inhibitors. Nat. Struct. Biol. 2:407-415.
    • (1995) Nat. Struct. Biol. , vol.2 , pp. 407-415
    • Ding, J.1    Das, K.2    Moereels, H.3    Koymans, L.4    Andries, K.5    Janssen, P.A.6    Hughes, S.H.7    Arnold, E.8
  • 23
    • 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 nonnucleoside inhibitor
    • Esnouf, R. M., J. Ren, A. L. Hopkins, C. K. Ross, E. Y. Jones, D. K. Stammers, and D. I. Stuart. 1997. 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 nonnucleoside inhibitor. Proc. Natl. Acad. Sci. USA 94:3984-3989.
    • (1997) Proc. Natl. Acad. Sci. USA , 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
  • 26
    • 0025968569 scopus 로고
    • The molecular biology of human immunodeficiency virus tvpe 1 infections
    • Greene, W. C. 1991. The molecular biology of human immunodeficiency virus tvpe 1 infections. N. Engl. J. Med. 324:308-317.
    • (1991) N. Engl. J. Med. , vol.324 , pp. 308-317
    • Greene, W.C.1
  • 28
    • 0030983790 scopus 로고    scopus 로고
    • The inhibitory activity of diazinyl-substituted thiourea derivatives on human immunodeficiency virus type 1 reverse transcriptase
    • Heinisch, G., B. Matuszczak, S. Pachler, and D. Rakowitz. 1997. The inhibitory activity of diazinyl-substituted thiourea derivatives on human immunodeficiency virus type 1 reverse transcriptase. Antiviral Chem. Chemother. 8: 443-446.
    • (1997) Antiviral Chem. Chemother. , vol.8 , pp. 443-446
    • Heinisch, G.1    Matuszczak, B.2    Pachler, S.3    Rakowitz, D.4
  • 29
    • 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., J. Ren, R. M. Esnouf, B. E. Willcox, E. Y. Jones, C. Ross, T. Miyasaka, R. T. Walker, H. Tanaka, D. K. Stammers, and D. I. Stuart. 1996. 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. 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
  • 30
    • 84889120137 scopus 로고
    • Improved methods for binding protein models in electron density maps and the location of errors in these models
    • Jones, T. A., J. Y. Zou, S. W. Cowan, and G. Kjeldgaard. 1991. Improved methods for binding protein models in electron density maps and the location of errors in these models. Acta Crystallogr. A 47:110-119.
    • (1991) Acta Crystallogr. A , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, G.4
  • 31
    • 0030070683 scopus 로고    scopus 로고
    • Selective pressure of a quinoxaline nonnucleoside inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) on HIV-1 replication results in the emergence of nucleoside RT-inhibitor-specific (RT Leu-74→Val or Ile and Val-75→Leu or Ile) HIV-1 mutants
    • Kleim, J. P., M. Rosner, I. Winkler, A. Paessens, R. Kirsch, Y. Hsiou, E. Arnold, and G. Riess. 1996. Selective pressure of a quinoxaline nonnucleoside inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) on HIV-1 replication results in the emergence of nucleoside RT-inhibitor-specific (RT Leu-74→Val or Ile and Val-75→Leu or Ile) HIV-1 mutants. Proc. Natl. Acad. Sci. USA 93:34-38.
    • (1996) Proc. Natl. Acad. Sci. USA , vol.93 , pp. 34-38
    • Kleim, J.P.1    Rosner, M.2    Winkler, I.3    Paessens, A.4    Kirsch, R.5    Hsiou, Y.6    Arnold, E.7    Riess, G.8
  • 32
    • 0026693137 scopus 로고
    • Crystal structure at 3.5 a resolution of HIV-1 reverse transcriptase complexed with an inhibitor
    • Kohlstaedt, L. A., J. Wang, J. M. Friedman, P. A. Rice, and T. A. Steitz. 1992. Crystal structure at 3.5 A resolution of HIV-1 reverse transcriptase complexed with an inhibitor. Science 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
  • 35
    • 0032544145 scopus 로고    scopus 로고
    • Structure-based design of N-[2-(1-piperidinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase
    • Mao, C., R. Vig, T. K. Venkatachalam, E. A. Sudbeck, and F. M. Uckun. 1998. Structure-based design of N-[2-(1-piperidinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea and N-[2-(1-piperazinylethyl)]-N′-[2-(5-bromopyridyl)]-thiourea as potent non-nucleoside inhibitors of HIV-1 reverse transcriptase. Bioorg. Med. Chem. Lett. 8:2213-2218.
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 2213-2218
    • Mao, C.1    Vig, R.2    Venkatachalam, T.K.3    Sudbeck, E.A.4    Uckun, F.M.5
  • 36
    • 0025186450 scopus 로고
    • Molecular targets for AIDS therapy
    • Mitsuya, H., R. Yarchoan, and S. Broder. 1990. Molecular targets for AIDS therapy. Science 249:1533-1544.
    • (1990) Science , vol.249 , pp. 1533-1544
    • Mitsuya, H.1    Yarchoan, R.2    Broder, S.3
  • 37
    • 0342384817 scopus 로고    scopus 로고
    • Molecular Simulations Inc., San Diego, Calif.
    • Molecular Simulations Inc. 1996. InsightII. Molecular Simulations Inc., San Diego, Calif.
    • (1996) InsightII
  • 39
    • 0030994577 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of novel N-1 side chain-modified analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)
    • Pontikis, R., R. Benhida, A. M. Aubertin, D. S. Grierson, and C. Monneret. 1997. Synthesis and anti-HIV activity of novel N-1 side chain-modified analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 40:1845-1854.
    • (1997) J. Med. Chem. , vol.40 , pp. 1845-1854
    • Pontikis, R.1    Benhida, R.2    Aubertin, A.M.3    Grierson, D.S.4    Monneret, C.5
  • 41
    • 0029645409 scopus 로고
    • The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: Lessons for inhibitor design
    • Ren, J., R. Esnouf, A. Hopkins, C. Ross, Y. Jones, D. Stammers, and D. Stuart. 1995. The structure of HIV-1 reverse transcriptase complexed with 9-chloro-TIBO: lessons for inhibitor design. Structure 3:915-926.
    • (1995) Structure , vol.3 , pp. 915-926
    • Ren, J.1    Esnouf, R.2    Hopkins, A.3    Ross, C.4    Jones, Y.5    Stammers, D.6    Stuart, D.7
  • 42
    • 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
    • Romero, D. L., R. A. Morge, M. J. Genin, C. Biles, M. Busso, L. Resnick, I. W. Althaus, F. Reusser, R. C. Thomas, and W. G. Tarpley. 1993. 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. 36:1505-1508.
    • (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
  • 45
    • 0026071537 scopus 로고
    • A new class of HIV-1-specific 6-substituted acyclouridine derivatives: Synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)
    • Tanaka, H., M. Baba, H. Hayakawa, T. Sakamaki, T. Miyasaka, M. Ubasawa, H. Takashima, K. Sekiya, I. Nitta, S. Shigeta, R. T. Walker, J. Balzarini, and E. De Clercq. 1991. A new class of HIV-1-specific 6-substituted acyclouridine derivatives: synthesis and anti-HIV-1 activity of 5-or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 34:349-357.
    • (1991) J. Med. Chem. , vol.34 , pp. 349-357
    • Tanaka, H.1    Baba, M.2    Hayakawa, H.3    Sakamaki, T.4    Miyasaka, T.5    Ubasawa, M.6    Takashima, H.7    Sekiya, K.8    Nitta, I.9    Shigeta, S.10    Walker, R.T.11    Balzarini, J.12    De Clercq, E.13
  • 46
    • 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., J. Ding, A. Jacobo Molina, R. G. Nanni, P. L. Boyer, S. H. Hughes, R. Pauwels, K. Andries, P. A. Janssen, and E. Arnold. 1994. 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. 243:369-387.
    • (1994) J. Mol. Biol. , vol.243 , pp. 369-387
    • Tantillo, C.1    Ding, J.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.9    Arnold, E.10
  • 48
    • 0031788490 scopus 로고    scopus 로고
    • Rational design and synthesis of phenethyl-5-bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase
    • Vig, R., C. Mao, T. K. Venkatachalan, L. Tuel-Ahlgren, E. A. Sudbeck, and F. M. Uckun. 1998. Rational design and synthesis of phenethyl-5-bromopyridyl thiourea derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase. Bioorg. Med. Chem. 6:1-9.
    • (1998) Bioorg. Med. Chem. , vol.6 , pp. 1-9
    • Vig, R.1    Mao, C.2    Venkatachalan, T.K.3    Tuel-Ahlgren, L.4    Sudbeck, E.A.5    Uckun, F.M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.