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Volumn 45, Issue 26, 2002, Pages 5721-5726

Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants

Author keywords

[No Author keywords available]

Indexed keywords

6 (3,5 DIMETHYLBENZYL) 5 ETHYL 1 (3 METHYLBUT 2 ENYLOXYMETHYL)URACIL; 6 (3,5 DIMETHYLBENZYL) 5 ETHYLURACIL DERIVATIVE; 6 BENZYL 1 (ETHOXYMETHYL) 5 ISOPROPYLURACIL; EMIVIRINE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

EID: 0037137588     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020949r     Document Type: Article
Times cited : (74)

References (27)
  • 1
    • 0025186450 scopus 로고
    • Molecular targets for AIDS therapy
    • Mitsuya, H.; Yarchoan, R.; Broder, S. Molecular targets for AIDS therapy. Science 1990, 249, 1533-1544.
    • (1990) Science , vol.249 , pp. 1533-1544
    • Mitsuya, H.1    Yarchoan, R.2    Broder, S.3
  • 2
    • 0025273418 scopus 로고
    • Targets and strategies for the antiviral chemotherapy of AIDS
    • De Clercq, E. Targets and strategies for the antiviral chemotherapy of AIDS. Trends Pharmacol. Sci. 1990, 11, 198-205.
    • (1990) Trends Pharmacol. Sci. , vol.11 , pp. 198-205
    • De Clercq, E.1
  • 3
    • 0032737069 scopus 로고    scopus 로고
    • Non-nucleoside reverse transcriptase inhibitors: The NNRTI boom
    • Pedersen, O. S.; Pedersen, E. B. Non-nucleoside reverse transcriptase inhibitors: The NNRTI boom. Antiviral Chem. Chemother. 1999, 10, 285-314.
    • (1999) Antiviral Chem. Chemother. , vol.10 , pp. 285-314
    • Pedersen, O.S.1    Pedersen, E.B.2
  • 5
    • 0029096567 scopus 로고
    • Synthesis and antiviral activity of 6-benzyl analogues 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 analogues 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
  • 6
    • 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
  • 9
    • 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
  • 14
    • 0031449527 scopus 로고    scopus 로고
    • A 3D QSAR study of a series of HEPT analogues: The influence of conformational mobility on HIV-1 reverse transcriptase inhibition
    • Kireev, D. B.; Chrétien, J. J.; Grierson, D. S.; Monneret, C. A 3D QSAR study of a series of HEPT analogues: The influence of conformational mobility on HIV-1 reverse transcriptase inhibition. J. Med. Chem. 1997, 40, 4257-4264.
    • (1997) J. Med. Chem. , vol.40 , pp. 4257-4264
    • Kireev, D.B.1    Chrétien, J.J.2    Grierson, D.S.3    Monneret, C.4
  • 15
    • 0022156092 scopus 로고
    • Quarternary ammonium salts in alkylation reactions (synthesis of formaldehyde acetals)
    • Nazaretyan, A. Kh.; Torosyan, G. O.; Babayan, A. T. Quarternary ammonium salts in alkylation reactions (synthesis of formaldehyde acetals). J. Appl. Chem. USSR 1985, 58, 2396-2400.
    • (1985) J. Appl. Chem. USSR , vol.58 , pp. 2396-2400
    • Nazaretyan, A.Kh.1    Torosyan, G.O.2    Babayan, A.T.3
  • 16
    • 0029111877 scopus 로고
    • Easy synthesis of 5,6-disubstituted acyclouridine derivatives
    • (a) Danel, K.; Larsen, E.; Pedersen, E. B. Easy synthesis of 5,6-disubstituted acyclouridine derivatives. Sythesis 1995, 8, 934-936.
    • (1995) Sythesis , vol.8 , pp. 934-936
    • Danel, K.1    Larsen, E.2    Pedersen, E.B.3
  • 17
    • 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
    • (b) Danel, K.; Larsen, E.; Pedersen, E. B.; Vestergaard, B. F.; Nielsen, C. Synthesis and potent anti-HIV-1 activity of novel 6-benzyluracil analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1996, 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
  • 18
    • 0031086857 scopus 로고    scopus 로고
    • Anti-HIV active naphthyl analogues of HEPT and DABO
    • (c) Danel, K.; Nielsen, C.; Pedersen, E. B. Anti-HIV active naphthyl analogues of HEPT and DABO. Acta Chem. Scand. 1997, 51, 426-430.
    • (1997) Acta Chem. Scand. , vol.51 , pp. 426-430
    • Danel, K.1    Nielsen, C.2    Pedersen, E.B.3
  • 19
    • 84981858603 scopus 로고
    • A new synthesis of nucleosides
    • Wittenburg, E. A new synthesis of nucleosides. Z. Chem. 1964, 4, 303-304.
    • (1964) Z. Chem. , vol.4 , pp. 303-304
    • Wittenburg, E.1
  • 20
    • 84982068675 scopus 로고
    • Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts
    • Vorbrüggen, H.; Krolikiewiecz, K.; Bennua, B. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255.
    • (1981) Chem. Ber. , vol.114 , pp. 1234-1255
    • Vorbrüggen, H.1    Krolikiewiecz, K.2    Bennua, B.3
  • 21
    • 0022404296 scopus 로고
    • Infection of HTLV-III/LAV in HTLV-I-carrying cells MT-2 and MT-4 and application in a plaque assay
    • Harada, S.; Koyanagi, Y.; Yamamoto, N. Infection of HTLV-III/LAV in HTLV-I-carrying cells MT-2 and MT-4 and application in a plaque assay. Science 1985, 229, 563-566.
    • (1985) Science , vol.229 , pp. 563-566
    • Harada, S.1    Koyanagi, Y.2    Yamamoto, N.3
  • 22
    • 0021237243 scopus 로고
    • Detection, isolation and continuous production of cytophathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS
    • Popovic, M.; Sarngadharan, M. G.; Read, E.; Gallo, R. C. Detection, isolation and continuous production of cytophathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS. Science 1984, 224, 497-500.
    • (1984) Science , vol.224 , pp. 497-500
    • Popovic, M.1    Sarngadharan, M.G.2    Read, E.3    Gallo, R.C.4
  • 23
    • 0021061819 scopus 로고
    • Rapid colorimetic assay for cellular growth and survival. Application to proliferation and cytotoxicity assays
    • Mosmann, T. Rapid colorimetic assay for cellular growth and survival. Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
    • (1983) J. Immunol. Methods , vol.65 , pp. 55-63
    • Mosmann, T.1
  • 24
    • 0021717961 scopus 로고
    • Molecular characterization of human T-cell leukemia (lymphotropic) virus type III in the acquired immune deficiency syndrome
    • Shaw, G. M.; Hahn, B. H.; Arya, S. K.; Groopman, J. E.; Gallo, R. C.; Wong-Staal, F. Molecular characterization of human T-cell leukemia (lymphotropic) virus type III in the acquired immune deficiency syndrome. Science 1984, 226, 1165-1171.
    • (1984) Science , vol.226 , pp. 1165-1171
    • Shaw, G.M.1    Hahn, B.H.2    Arya, S.K.3    Groopman, J.E.4    Gallo, R.C.5    Wong-Staal, F.6
  • 25
    • 0026318387 scopus 로고
    • Human immunodeficiency virus type 1 mutants resistant to nonnucleoside inhibitors of reverse transcriptase arise in tissue culture
    • (a) Richman, D.; Shih, C. K.; Lowy, I.; Rose, J.; Prodanovich, P.; Goff, S.; Griffin, J. Human immunodeficiency virus type 1 mutants resistant to nonnucleoside inhibitors of reverse transcriptase arise in tissue culture. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 11241-11245.
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 11241-11245
    • Richman, D.1    Shih, C.K.2    Lowy, I.3    Rose, J.4    Prodanovich, P.5    Goff, S.6    Griffin, J.7
  • 26
    • 0030992580 scopus 로고    scopus 로고
    • Tetrahydronaphthalene lignan compounds as potent anti-HIV type 1 agents
    • (b) Hara, H.; Fujihashi, T.; Sakata, T.; Kaji, A.; Kaji, H. Tetrahydronaphthalene lignan compounds as potent anti-HIV type 1 agents. AIDS Res. Hum. Retroviruses 1997, 13, 6695-705.
    • (1997) AIDS Res. Hum. Retroviruses , vol.13 , pp. 6695-6705
    • Hara, H.1    Fujihashi, T.2    Sakata, T.3    Kaji, A.4    Kaji, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.