메뉴 건너뛰기




Volumn 39, Issue 17, 1996, Pages 3418-3422

Synthesis and antiretroviral evaluation of new alkoxy and aryloxy phosphate derivatives of 3'-azido-3'-deoxythymidine

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; ZIDOVUDINE DERIVATIVE;

EID: 0029761595     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950777g     Document Type: Article
Times cited : (19)

References (16)
  • 3
    • 0028220406 scopus 로고
    • Synthesis and antiviral activity of 3′-azido-3′-deoxythymidine triphosphate distearoylglycerol: A novel phospholipid conjugate of the anti-HIV agent AZT
    • Van Wijk, G. M; T.; Hostetler, K. Y.; Kroneman, E.; Richman, D. D.; Sridhar, C. N.; Kumar, R.; van der Bosch, H. Synthesis and antiviral activity of 3′-azido-3′-deoxythymidine triphosphate distearoylglycerol: a novel phospholipid conjugate of the anti-HIV agent AZT. Chem. Phys. Lipids 1994, 70, 213-222.
    • (1994) Chem. Phys. Lipids , vol.70 , pp. 213-222
    • Van Wijk, G.M.T.1    Hostetler, K.Y.2    Kroneman, E.3    Richman, D.D.4    Sridhar, C.N.5    Kumar, R.6    Van Der Bosch, H.7
  • 4
    • 0026662054 scopus 로고
    • Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3′-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3′-deoxythymidine
    • Hostetler, K. Y.; Richman, D. D.; Carson, D. A.; Stuhmiller, L. M.; van Wijk, G. M. T.; van den Bosch, H. Greatly enhanced inhibition of human immunodeficiency virus type 1 replication in CEM and HT4-6C cells by 3′-deoxythymidine diphosphate dimyristoylglycerol, a lipid prodrug of 3′-deoxythymidine. Antimicrob. Agents Chemother. 1992, 36, 2025-2029.
    • (1992) Antimicrob. Agents Chemother. , vol.36 , pp. 2025-2029
    • Hostetler, K.Y.1    Richman, D.D.2    Carson, D.A.3    Stuhmiller, L.M.4    Van Wijk, G.M.T.5    Van Den Bosch, H.6
  • 5
    • 0025814856 scopus 로고
    • Lipophilic glycosyl phosphotriester derivatives of AZT: Synthesis, NMR transmembrane transport study, and antiviral activity
    • Benin, Y.; Gouyette, C.; Schwartz, O.; Debouzy, J.-C.; Neumann, J.-M.; Huynh-Dinh, T. Lipophilic glycosyl phosphotriester derivatives of AZT: Synthesis, NMR transmembrane transport study, and antiviral activity. J. Med. Chem. 1991, 34, 1830-1837.
    • (1991) J. Med. Chem. , vol.34 , pp. 1830-1837
    • Benin, Y.1    Gouyette, C.2    Schwartz, O.3    Debouzy, J.-C.4    Neumann, J.-M.5    Huynh-Dinh, T.6
  • 6
    • 0025895220 scopus 로고
    • Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity
    • Piantadosi, C.; Marasco, C. J., Jr.; Morris-Natschke, S. L.; Meyer, K. L.; Gumus, M. E. Synthesis and evaluation of novel ether lipid nucleoside conjugates for anti-HIV-1 activity. J. Med. Chem. 1991, 34, 1408-1414.
    • (1991) J. Med. Chem. , vol.34 , pp. 1408-1414
    • Piantadosi, C.1    Marasco Jr., C.J.2    Morris-Natschke, S.L.3    Meyer, K.L.4    Gumus, M.E.5
  • 7
    • 0027050423 scopus 로고
    • O-Alkyl-5′,5′-dinucleoside phosphates as prodrugs of 3′-azidothymidine and cordycepin
    • Meier, C.; Neumann, J.-M.; Andre, F.; Hennin, Y.; Huynh-Dinh, T. O-Alkyl-5′,5′-dinucleoside phosphates as prodrugs of 3′-azidothymidine and cordycepin. J. Org. Chem. 1992, 57, 7300-7308.
    • (1992) J. Org. Chem. , vol.57 , pp. 7300-7308
    • Meier, C.1    Neumann, J.-M.2    Andre, F.3    Hennin, Y.4    Huynh-Dinh, T.5
  • 8
    • 0027433373 scopus 로고
    • Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process
    • Puech, F.; Gosselin, G.; Lefebvre, I.; Pompon, A.; Aubertin, A. M.; Kirn, A.; Imbach, J. L. Intracellular delivery of nucleoside monophosphates through a reductase-mediated activation process. Antiviral Res. 1993, 22, 155-174.
    • (1993) Antiviral Res. , vol.22 , pp. 155-174
    • Puech, F.1    Gosselin, G.2    Lefebvre, I.3    Pompon, A.4    Aubertin, A.M.5    Kirn, A.6    Imbach, J.L.7
  • 9
    • 0027412437 scopus 로고
    • Synthesis and anti-HIV evaluation of D4T and D4T 5′-monophosphate prodrugs
    • Sergheraert, C.; Pierlot, C.; Tartar, A.; Henin, Y.; Lemaitre, M. Synthesis and anti-HIV evaluation of D4T and D4T 5′-monophosphate prodrugs. J. Med. Chem. 1993, 36, 826-830.
    • (1993) J. Med. Chem. , vol.36 , pp. 826-830
    • Sergheraert, C.1    Pierlot, C.2    Tartar, A.3    Henin, Y.4    Lemaitre, M.5
  • 10
    • 0028258723 scopus 로고
    • Diaryl phosphate derivatives act as pro-drugs of AZT with reduced cytotoxicity compared to the parent nucleoside
    • McGuigan, C.; Pathirana, R. N.; Davies, M. P. H.; Balzarini, J.; De Clercq, E. Diaryl phosphate derivatives act as pro-drugs of AZT with reduced cytotoxicity compared to the parent nucleoside. Bioorg. Med. Chem. Lett. 1994, 4, 427-430.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 427-430
    • McGuigan, C.1    Pathirana, R.N.2    Davies, M.P.H.3    Balzarini, J.4    De Clercq, E.5
  • 11
    • 0027284753 scopus 로고
    • Intracellular delivery of bioactive AZT nucleotides by aryl phosphate derivatives of AZT
    • McGuigan, C.; Pathirana, R. N.; 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
  • 14
    • 0021237243 scopus 로고
    • Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS
    • Popovic, M.; Sarngadharan, M. C.; Read, E.; Gallo, R. C. Detection, isolation, and continuous production of cytopathic 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.C.2    Read, E.3    Gallo, R.C.4
  • 15
    • 0025979184 scopus 로고
    • 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) effectively inhibits retrovirus replication in vitro and simian immunodeficiency virus-infection in rhesus-monkeys
    • Balzarini, J.; Naesens, L.; Slachmuylders, J.; Niphuis, H.; Rosenberg, I.; Holy, A.; Schellekens, H.; De Clercq, E. 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) effectively inhibits retrovirus replication in vitro and simian immunodeficiency virus-infection in rhesus-monkeys. AIDS 1991, 5, 21-28.
    • (1991) AIDS , vol.5 , pp. 21-28
    • Balzarini, J.1    Naesens, L.2    Slachmuylders, J.3    Niphuis, H.4    Rosenberg, I.5    Holy, A.6    Schellekens, H.7    De Clercq, E.8
  • 16
    • 10144224034 scopus 로고    scopus 로고
    • note
    • 50 (50% cytotoxic concentration) is the concentration of compound which causes a 50% reduction in cell viability. The SI (selectivity index) is the ratio of 50% cytotoxic concentration to 50% antivirally effective concentration. For full details, see ref 15.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.