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Volumn 20, Issue 4, 2010, Pages 153-160

The design, synthesis and antiviral evaluation of a series of 5-trimethylsilyl-1-β-D-(arabinofuranosyl) uracil phosphoramidate ProTides

Author keywords

[No Author keywords available]

Indexed keywords

5 TRIMETHYLSILYL 1 BETA DEXTRO(ARABINOFURANOSYL)URACIL; BENZYL 2 [[[5 [2,4 DIOXO 5 [(TRIMETHYLSILYL)ETHYNYL] 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY TETRAHYDROFURAN 2 YL]METHOXY](NAPHTHALEN 1 YLOXY)PHOSPHORYLAMINO]PROPANOATE; METHYL 2 [[[5 [2,4 DIOXO 5 [(TRIMETHYLSILYL)ETHYNYL] 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY TETRAHYDROFURAN 2 YL]METHOXY](NAPHTHALEN 1 YLOXY)PHOSPHORYLAMINO] 3 METHYLBUTANOATE; METHYL 2 [[[5 [2,4 DIOXO 5 [(TRIMETHYLSILYL)ETHYNYL] 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3,4 DIHYDROXY TETRAHYDROFURAN 2 YL]METHOXY](NAPHTHALEN 1 YLOXY)PHOSPHORYLAMINO]PROPANOATE; PHOSPHORAMIDIC ACID DERIVATIVE; TERT BUTYL 2 [[[5 [2,4 DIOXO 5 [(TRIMETHYLSILYL)ETHYNYL] 3,4 DIHYDROPYRIMIDIN 1(2H) YL] 3 ,4 DIHYDROXY TETRAHYDROFURAN 2 YL]METHOXY](NAPHTHALEN 1 YLOXY)PHOSPHORYLAMINO]PROPANOATE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

EID: 77949675605     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.3851/IMP1476     Document Type: Article
Times cited : (4)

References (18)
  • 1
    • 0028205185 scopus 로고
    • Metabolism and mechanism of antiretroviral action of purine and pyrimidine derivatives
    • Balzarini J. Metabolism and mechanism of antiretroviral action of purine and pyrimidine derivatives. Pharm World Sci 1994; 16:113-126.
    • (1994) Pharm World Sci , vol.16 , pp. 113-126
    • Balzarini, J.1
  • 2
    • 48349089930 scopus 로고    scopus 로고
    • 2′-Deoxy- 4′-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants
    • Kawamoto A, Kodama E, Sarafianos SG, et al. 2′-Deoxy- 4′-C-ethynyl-2-halo-adenosines active against drug-resistant human immunodeficiency virus type 1 variants. Int J Biochem Cell Biol 2008; 40:2410-2420.
    • (2008) Int J Biochem Cell Biol , vol.40 , pp. 2410-2420
    • Kawamoto, A.1    Kodama, E.2    Sarafianos, S.G.3
  • 3
    • 41149166259 scopus 로고    scopus 로고
    • Synthesis and anti-HIV activity of 4′-substituted 4′-thiothymidines: A new entry based on nucleophilic substitution of the 4′-acetoxy group
    • Haraguchi K, Shimada H, Tanaka H, et al. Synthesis and anti-HIV activity of 4′-substituted 4′-thiothymidines: a new entry based on nucleophilic substitution of the 4′-acetoxy group. J Med Chem 2008; 51:1885-1893.
    • (2008) J Med Chem , vol.51 , pp. 1885-1893
    • Haraguchi, K.1    Shimada, H.2    Tanaka, H.3
  • 4
    • 0141558904 scopus 로고    scopus 로고
    • Synthesis of 4′-ethynylpurine nucleosides possessing anti-HIV activity
    • Kitano K, Sakata S, Kohgo S, et al. Synthesis of 4′-ethynylpurine nucleosides possessing anti-HIV activity. Nucleic Acids Symp Ser 2000; 44:105-106.
    • (2000) Nucleic Acids Symp Ser , vol.44 , pp. 105-106
    • Kitano, K.1    Sakata, S.2    Kohgo, S.3
  • 5
    • 0035342161 scopus 로고    scopus 로고
    • 4′-C-substituted-2′-deoxynucleosides: A family of antiretroviral agents which are potent against drug-resistant HIV variants
    • Ohrui H, Mitsuya H. 4′-C-substituted-2′-deoxynucleosides: a family of antiretroviral agents which are potent against drug-resistant HIV variants. Curr Drug Targets Infect Disord 2001; 1:1-10.
    • (2001) Curr Drug Targets Infect Disord , vol.1 , pp. 1-10
    • Ohrui, H.1    Mitsuya, H.2
  • 6
    • 0034676266 scopus 로고    scopus 로고
    • Syntheses of 4′-Cethynyl-beta-D-arabino- and 4′-C-ethynyl-2′- deoxy-beta-dribo-pentofuranosylpyrimidines and -purines and evaluation of their anti-HIV activity
    • Ohrui H, Kohgo S, Kitano K, et al. Syntheses of 4′-Cethynyl-beta-D-arabino- and 4′-C-ethynyl-2′- deoxy-beta-dribo-pentofuranosylpyrimidines and -purines and evaluation of their anti-HIV activity. J Med Chem 2000; 43:4516-4525.
    • (2000) J Med Chem , vol.43 , pp. 4516-4525
    • Ohrui, H.1    Kohgo, S.2    Kitano, K.3
  • 7
    • 33750999341 scopus 로고    scopus 로고
    • Structure of vaccinia virus thymidine kinase in complex with dTTP: Insights for drug design
    • El Omari K, Solaroli N, Karlsson A, Balzarini J, Stammers DK. Structure of vaccinia virus thymidine kinase in complex with dTTP: insights for drug design. BMC Struct Biol 2006; 6:22-31.
    • (2006) BMC Struct Biol , vol.6 , pp. 22-31
    • El Omari, K.1    Solaroli, N.2    Karlsson, A.3    Balzarini, J.4    Stammers, D.K.5
  • 8
    • 34250199397 scopus 로고    scopus 로고
    • Design, synthesis, and anti-HIV activity of 2′,3′-didehydro-2′,3′- dideoxyuridine (d4U), 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives
    • Mehellou Y, McGuigan C, Brancale A, Balzarini J. Design, synthesis, and anti-HIV activity of 2′,3′-didehydro-2′,3′- dideoxyuridine (d4U), 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives. Bioorg Med Chem Lett 2007; 17:3666-3669.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 3666-3669
    • Mehellou, Y.1    McGuigan, C.2    Brancale, A.3    Balzarini, J.4
  • 9
    • 67650478382 scopus 로고    scopus 로고
    • An investigation into the anti-HIV activity of 2′,3′-didehydro-2′,3′-dideoxyuridine (d4U) and 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives
    • Mehellou Y, Balzarini J, McGuigan C. An investigation into the anti-HIV activity of 2′,3′-didehydro-2′,3′-dideoxyuridine (d4U) and 2′,3′-dideoxyuridine (ddU) phosphoramidate 'ProTide' derivatives. Org Biomol Chem 2009; 7:2548-2553.
    • (2009) Org Biomol Chem , vol.7 , pp. 2548-2553
    • Mehellou, Y.1    Balzarini, J.2    McGuigan, C.3
  • 11
    • 3042538806 scopus 로고    scopus 로고
    • Selenium derivatization and crystallization of DNA and RNA oligonucleotides for X-ray crystallography using multiple anomalous dispersion
    • Carrasco N, Buzin Y, Tyson E, Halpert E, Huang Z. Selenium derivatization and crystallization of DNA and RNA oligonucleotides for X-ray crystallography using multiple anomalous dispersion. Nucleic Acids Res 2004; 32:1638-1646.
    • (2004) Nucleic Acids Res , vol.32 , pp. 1638-1646
    • Carrasco, N.1    Buzin, Y.2    Tyson, E.3    Halpert, E.4    Huang, Z.5
  • 12
    • 13444261067 scopus 로고    scopus 로고
    • Synthesis and anti-viral activity of a series of D- and L-2′-deoxy-2′- fluororibonucleosides in the subgenomic HCV replicon system
    • Shi J, Du J, Ma T, et al. Synthesis and anti-viral activity of a series of D- and L-2′-deoxy-2′- fluororibonucleosides in the subgenomic HCV replicon system. Bioorg Med Chem 2005; 13:1641-1652.
    • (2005) Bioorg Med Chem , vol.13 , pp. 1641-1652
    • Shi, J.1    Du, J.2    Ma, T.3
  • 13
    • 0024999263 scopus 로고
    • Cerium(IV)-mediated halogenation at the C-5 of uracil derivatives
    • Asakura J, Robins MJ. Cerium(IV)-mediated halogenation at the C-5 of uracil derivatives. J Org Chem 1990; 55:4928-4933.
    • (1990) J Org Chem , vol.55 , pp. 4928-4933
    • Asakura, J.1    Robins, M.J.2
  • 14
    • 33947727055 scopus 로고    scopus 로고
    • The Sonogashira reaction: A booming methodology in synthetic organic chemistry
    • Chinchilla R, Najera C. The Sonogashira reaction: a booming methodology in synthetic organic chemistry. Chem Rev 2007; 107:874-922.
    • (2007) Chem Rev , vol.107 , pp. 874-922
    • Chinchilla, R.1    Najera, C.2
  • 15
    • 0027284753 scopus 로고
    • Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT
    • McGuigan C, Pathirana RN, Balzarini J, De Clercq E. Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT. J Med Chem 1993; 36:1048-1052.
    • (1993) J Med Chem , vol.36 , pp. 1048-1052
    • McGuigan, C.1    Pathirana, R.N.2    Balzarini, J.3    De Clercq, E.4
  • 16
    • 0029975897 scopus 로고    scopus 로고
    • Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite
    • McGuigan C, Cahard D, Sheeka HM, De Clercq E, Balzarini J. Aryl phosphoramidate derivatives of d4T have improved anti-HIV efficacy in tissue culture and may act by the generation of a novel intracellular metabolite. J Med Chem 1996; 39:1748-1753.
    • (1996) J Med Chem , vol.39 , pp. 1748-1753
    • McGuigan, C.1    Cahard, D.2    Sheeka, H.M.3    De Clercq, E.4    Balzarini, J.5
  • 17
    • 0030872397 scopus 로고    scopus 로고
    • Phosphoramidate derivatives of d4T as inhibitors of HIV: The effect of amino acid variation
    • McGuigan C, Tsang HW, Cahard D, et al. Phosphoramidate derivatives of d4T as inhibitors of HIV: the effect of amino acid variation. Antiviral Res 1997; 35:195-204.
    • (1997) Antiviral Res , vol.35 , pp. 195-204
    • McGuigan, C.1    Tsang, H.W.2    Cahard, D.3
  • 18
    • 34250888819 scopus 로고    scopus 로고
    • 5-Alkynyl analogs of arabinouridine and 2′-deoxyuridine: Cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells
    • Cristofoli WA, Wiebe LI, De Clercq E, et al. 5-Alkynyl analogs of arabinouridine and 2′-deoxyuridine: cytostatic activity against herpes simplex virus and varicella-zoster thymidine kinase gene-transfected cells. J Med Chem 2007; 50:2851-2857.
    • (2007) J Med Chem , vol.50 , pp. 2851-2857
    • Cristofoli, W.A.1    Wiebe, L.I.2    De Clercq, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.