메뉴 건너뛰기




Volumn 48, Issue 8, 2005, Pages 2867-2875

Design, synthesis, and antiviral activity of adenosine 5′-phosphonate analogues as chain terminators against hepatitis C virus

Author keywords

[No Author keywords available]

Indexed keywords

9 [2,3 DIHYDROXY 4 (PHOSPHONOMETHOXY)CYCLOPENT 1 YL]ADENINE; 9 [2,3 DIHYDROXY 4 [(HYDROXYPYROPHOSPHOROXY)PHOSPHONOMETHOXY]CYCLOPENT 1 YL]ADENINE; 9 [5' DEOXY 5' [(HYDROXYPYROPHOSPHOROXY)PHOSPHINYL]BETA RIBOFURANOSYL]ADENINE; 9 [5',6' DIDEOXY 6' (HYDROXYPHOSPHINYL) BETA RIBOHEXOFURANOSYL]ADENINE; 9 [5',6' DIDEOXY 6' (HYDROXYPYROPHOSPHOROXY)PHOSPHINYL] BETA RIBOHEXOFURANOSYL]ADENINE; 9 [5',6' DIDEOXY 6' [(HYDROXYPYROPHOSPHOROXY)PHOSPHINYL] 2' C METHYL BETA RIBOHEXOFURANOSYL]ADENINE; 9 [TETRAHYDRO 3,4 DIHYDROXY 5 [(HYDROXYLPYROPHOSPHOROXY)PHOSPHONOMETHOXY] 2 FURANYL]ADENINE; ADEFOVIR; ADENOSINE KINASE; ADENOSINE TRIPHOSPHATE; CIDOFOVIR; NUCLEOSIDE MONOPHOSPHATE KINASE; PHOSPHONIC ACID DERIVATIVE; PRODRUG; PYROPHOSPHATE; RNA DIRECTED RNA POLYMERASE; TENOFOVIR; UNCLASSIFIED DRUG;

EID: 17444388557     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049029u     Document Type: Article
Times cited : (91)

References (31)
  • 1
    • 0024509701 scopus 로고
    • Isolation of a cDNA clone derived from a blood-borne non-A, non-B viral hepatitis genome
    • Choo, Q. L.; Kuo, G.; Weiner, A. J.; Overby, L. R.; Bradley, D. W.; M., H. Isolation of a cDNA clone derived from a blood-borne non-A, non-B viral hepatitis genome. Science 1989, 244, 359-362.
    • (1989) Science , vol.244 , pp. 359-362
    • Choo, Q.L.1    Kuo, G.2    Weiner, A.J.3    Overby, L.R.4    Bradley, D.W.5
  • 2
    • 0030588528 scopus 로고    scopus 로고
    • Seroprevalence of hepatitis C virus (HCV) in a population sample
    • World Health Organization Hepatitis C. Seroprevalence of hepatitis C virus (HCV) in a population sample. Week. Epidemiol. Rec. 1996, 71, 346-349.
    • (1996) Week. Epidemiol. Rec. , vol.71 , pp. 346-349
  • 3
    • 0035934568 scopus 로고    scopus 로고
    • Peginterferon alfa-2b plus ribavirin compared with interferon alfa-2b plus ribavirin for initial treatment of chronic hepatitis C: A randomised trial
    • Manns, M. P.; McHutchison, J. G.; Gordon, S. C.; Rustgi, V. K.; Shiffman, M.; Reindollar, R.; Goodman, Z. D.; Koury, K.; Ling, M.; Albrecht, J. K. Peginterferon alfa-2b plus ribavirin compared with interferon alfa-2b plus ribavirin for initial treatment of chronic hepatitis C: A randomised trial. Lancet 2001, 358, 958-965.
    • (2001) Lancet , vol.358 , pp. 958-965
    • Manns, M.P.1    McHutchison, J.G.2    Gordon, S.C.3    Rustgi, V.K.4    Shiffman, M.5    Reindollar, R.6    Goodman, Z.D.7    Koury, K.8    Ling, M.9    Albrecht, J.K.10
  • 4
    • 0141426816 scopus 로고    scopus 로고
    • Targeting NS5B RNA-dependent RNA polymerase for anti-HCV chemotherapy
    • Wu, J. Z.; Hong, Z. Targeting NS5B RNA-dependent RNA polymerase for anti-HCV chemotherapy. Curr. Drug Targets Infect. Disord. 2003, 3, 207-219.
    • (2003) Curr. Drug Targets Infect. Disord. , vol.3 , pp. 207-219
    • Wu, J.Z.1    Hong, Z.2
  • 5
    • 0345138983 scopus 로고    scopus 로고
    • Phosphonomethoxyalkyl analogues of nucleotides
    • Holy, A. Phosphonomethoxyalkyl analogues of nucleotides. Curr. Pharm. Des. 2003, 9, 2567-2592.
    • (2003) Curr. Pharm. Des. , vol.9 , pp. 2567-2592
    • Holy, A.1
  • 6
    • 0029689120 scopus 로고    scopus 로고
    • Structure-activity relationships for phosphorylation of nucleoside analogues to monophosphates by nucleoside kinases
    • Johansson, N. G.; Eriksson, S. Structure-activity relationships for phosphorylation of nucleoside analogues to monophosphates by nucleoside kinases. Acta Biochim. Pol. 1996, 43, 143-160.
    • (1996) Acta Biochim. Pol. , vol.43 , pp. 143-160
    • Johansson, N.G.1    Eriksson, S.2
  • 9
    • 0027534661 scopus 로고
    • Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)- 2,6-diaminopurine
    • Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2- phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 1993, 37, 332-338.
    • (1993) Antimicrob. Agents Chemother. , vol.37 , pp. 332-338
    • Balzarini, J.1    Holy, A.2    Jindrich, J.3    Naesens, L.4    Snoeck, R.5    Schols, D.6    De Clercq, E.7
  • 10
    • 0032538456 scopus 로고
    • Selective Inhibition of HIV-1 Reverse transcriptase by an antiviral inhibitor, (R)-9-(2-phosphonylmethoxypropyl)adenine
    • Suo, Z.; Johnson, K. A. Selective Inhibition of HIV-1 Reverse transcriptase by an antiviral inhibitor, (R)-9-(2-phosphonylmethoxypropyl) adenine. J. Biol. Chem. 1938, 273, 27250-27258.
    • (1938) J. Biol. Chem. , vol.273 , pp. 27250-27258
    • Suo, Z.1    Johnson, K.A.2
  • 11
    • 0024382735 scopus 로고
    • Synthesis and biological properties of purine and pyrimidine 5′-deoxy-5′-(dihydroxyphosphinyl)-beta-D-ribofuranosyl analogues of AMP, GMP, IMP, and CMP
    • Raju, N.; Smee, D. F.; Robins, R. K.; Vaghefi, M. M. Synthesis and biological properties of purine and pyrimidine 5′-deoxy-5′- (dihydroxyphosphinyl)-beta-D-ribofuranosyl analogues of AMP, GMP, IMP, and CMP. J. Med. Chem. 1989, 32, 1307-1313.
    • (1989) J. Med. Chem. , vol.32 , pp. 1307-1313
    • Raju, N.1    Smee, D.F.2    Robins, R.K.3    Vaghefi, M.M.4
  • 12
    • 0026523383 scopus 로고
    • Synthesis of phosphonate analogues of dideoxyadenosine (DDA)-, dideoxycytidine (DDC)-, dideoxyinosine (DDI)-, and deoxythymidine (DDT)-5′-monophosphates
    • Secrist, J. A., 3rd; Riggs, R. M.; Comber, R. N.; Montgomery, J. A. Synthesis of phosphonate analogues of dideoxyadenosine (DDA)-, dideoxycytidine (DDC)-, dideoxyinosine (DDI)-, and deoxythymidine (DDT)-5′-monophosphates. Nucleosides, Nucleotides 1992, 11, 947-956.
    • (1992) Nucleosides, Nucleotides , vol.11 , pp. 947-956
    • Secrist III, J.A.1    Riggs, R.M.2    Comber, R.N.3    Montgomery, J.A.4
  • 14
    • 0001140507 scopus 로고
    • Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: Synthesis of phosphonate nucleotide analogs with potent activity against HIV
    • Kim, C. U.; Luh, B. Y.; Martin, J. C. Regiospecific and highly stereoselective electrophilic addition to furanoid glycals: Synthesis of phosphonate nucleotide analogs with potent activity against HIV. J. Org. Chem. 1991, 56, 2642-2647.
    • (1991) J. Org. Chem. , vol.56 , pp. 2642-2647
    • Kim, C.U.1    Luh, B.Y.2    Martin, J.C.3
  • 17
    • 0027722026 scopus 로고
    • Rational design for cytosolic delivery of nucleoside monphosphates: "SATE" and "DTE" as enzyme-labile transient phosphate protecting groups
    • Périgaud, C.; Gosselin, G.; Lefebvre, I.; Girardet, J. L.; Benzaria, S.; Barber, I.; Imbach, J. L. Rational design for cytosolic delivery of nucleoside monphosphates: "SATE" and "DTE" as enzyme-labile transient phosphate protecting groups. Bioorg. Med. Chem. Lett. 1993, 3, 2521-2526.
    • (1993) Bioorg. Med. Chem. Lett. , vol.3 , pp. 2521-2526
    • Périgaud, C.1    Gosselin, G.2    Lefebvre, I.3    Girardet, J.L.4    Benzaria, S.5    Barber, I.6    Imbach, J.L.7
  • 18
    • 33947331568 scopus 로고
    • The synthesis of 6′-deoxyhomonucleoside 6′-phosphonic acids
    • Jones, G. H.; Moffatt, J. G. The synthesis of 6′- deoxyhomonucleoside 6′-phosphonic acids. J. Am. Chem. Soc. 1868, 90, 5337-5338.
    • (1868) J. Am. Chem. Soc. , vol.90 , pp. 5337-5338
    • Jones, G.H.1    Moffatt, J.G.2
  • 19
    • 84985239894 scopus 로고
    • Darstellung und konformationszuordnung einiger 5′-homologer adenosinderivate
    • Hollmann, J.; Schlimme, E. Darstellung und Konformationszuordnung einiger 5′-homologer adenosinderivate. Liebigs Ann. Chem. 1884, 98-107.
    • (1884) Liebigs Ann. Chem. , pp. 98-107
    • Hollmann, J.1    Schlimme, E.2
  • 20
    • 0001278263 scopus 로고
    • Stable Wittig reagent suitable for the synthesis of α,β- unsaturated phosphonates
    • Jones, G. H.; Hamamura, E. K.; Moffatt, J. G. Stable Wittig reagent suitable for the synthesis of α,β-unsaturated phosphonates. Tetrahedron Lett. 1868, 55, 5731-5734.
    • (1868) Tetrahedron Lett. , vol.55 , pp. 5731-5734
    • Jones, G.H.1    Hamamura, E.K.2    Moffatt, J.G.3
  • 21
    • 37049086424 scopus 로고
    • Synthesis of optically active 5′-noraristeromycin: Enzyme-catalysed kinetic resolution of 9-(4-hydroxycyclopent-2-enyl)purines
    • Merlo, V.; Reece, F. J.; Roberts, S. M.; Gregson, M.; Storer, R. Synthesis of optically active 5′-noraristeromycin: Enzyme-catalysed kinetic resolution of 9-(4-hydroxycyclopent-2-enyl)purines. J. Chem. Soc. Perkin Trans. 1 1993, 15, 1717-1718.
    • (1993) J. Chem. Soc. Perkin Trans. 1 , vol.15 , pp. 1717-1718
    • Merlo, V.1    Reece, F.J.2    Roberts, S.M.3    Gregson, M.4    Storer, R.5
  • 22
    • 0028897039 scopus 로고
    • Stereocontrolled synthesis of the four stereoisomeric diphosphorylphosphonates of carbocyclic 2′,3′-dideoxy-2′, 3′-didehydro-5′-noradenosine
    • Dyatkina, N. B.; Theil, F.; Janta-Lipinski, M. Stereocontrolled synthesis of the four stereoisomeric diphosphorylphosphonates of carbocyclic 2′,3′-dideoxy-2′,3′-didehydro-5′-noradenosine. Tetrahedron 1995, 51, 761-772.
    • (1995) Tetrahedron , vol.51 , pp. 761-772
    • Dyatkina, N.B.1    Theil, F.2    Janta-Lipinski, M.3
  • 23
    • 0029075701 scopus 로고
    • Synthesis of four stereisomers of carbocyclic 5′-NOR D4A and evaluation of their triphosphates as substrates for DNA polymerases
    • Dyatkina, N.; Semizarov, D.; Victorova, L.; Krayevsky, A.; Theil, F.; Janta-Lipinski, M. Synthesis of four stereisomers of carbocyclic 5′-NOR D4A and evaluation of their triphosphates as substrates for DNA polymerases. Nucleosides, Nucleotides 1995, 14, 723-726.
    • (1995) Nucleosides, Nucleotides , vol.14 , pp. 723-726
    • Dyatkina, N.1    Semizarov, D.2    Victorova, L.3    Krayevsky, A.4    Theil, F.5    Janta-Lipinski, M.6
  • 24
    • 0030894115 scopus 로고    scopus 로고
    • A short, flexible route toward 2′-branched ribonucleosides
    • Harry-O'Kuru, R. E.; Smith, J. M.; Wolfe, M. S. A short, flexible route toward 2′-branched ribonucleosides. J. Org. Chem. 1997, 62, 1754-1759.
    • (1997) J. Org. Chem. , vol.62 , pp. 1754-1759
    • Harry-O'Kuru, R.E.1    Smith, J.M.2    Wolfe, M.S.3
  • 25
    • 0037721329 scopus 로고    scopus 로고
    • Canonical 3′-deoxyribonucleotides as a chain terminator for HCV NS5B RNA-dependent RNA polymerase
    • Shim, J.; Larson, G.; Lai, V.; Naim, S.; Wu, J. Z. Canonical 3′-deoxyribonucleotides as a chain terminator for HCV NS5B RNA-dependent RNA polymerase. Antivir. Res. 2003, 58, 243-251.
    • (2003) Antivir. Res. , vol.58 , pp. 243-251
    • Shim, J.1    Larson, G.2    Lai, V.3    Naim, S.4    Wu, J.Z.5
  • 26
    • 0036631865 scopus 로고    scopus 로고
    • Selection of 3′-template bases and initiating nucleotides by hepatitis C virus NS5B RNA-dependent RNA polymerase
    • Shim, J. H.; Larson, G.; Wu, J. Z.; Hong, Z. Selection of 3′-template bases and initiating nucleotides by hepatitis C virus NS5B RNA-dependent RNA polymerase. J. Virol. 2002, 76, 7030-7039.
    • (2002) J. Virol. , vol.76 , pp. 7030-7039
    • Shim, J.H.1    Larson, G.2    Wu, J.Z.3    Hong, Z.4
  • 27
    • 0024515139 scopus 로고
    • Sequence-specific inhibition of DNA strand elongation by incorporation of 9-beta-D-arabinofuranosyladenine
    • Ohno, Y.; Spriggs, D.; Matsukage, A.; Ohno, T.; Kufe, D. Sequence-specific inhibition of DNA strand elongation by incorporation of 9-beta-D-arabinofuranosyladenine. Cancer Res. 1989, 49, 2077-2081.
    • (1989) Cancer Res. , vol.49 , pp. 2077-2081
    • Ohno, Y.1    Spriggs, D.2    Matsukage, A.3    Ohno, T.4    Kufe, D.5
  • 28
    • 0023915751 scopus 로고
    • Effects of 1-beta-D-arabinofuranosylcytosine incorporation on elongation of specific DNA sequences by DNA polymerase beta
    • Ohno, Y.; Spriggs, D.; Matsukage, A.; Ohno, T.; Kufe, D. Effects of 1-beta-D-arabinofuranosylcytosine incorporation on elongation of specific DNA sequences by DNA polymerase beta. Cancer Res. 1988, 48, 1494-1498.
    • (1988) Cancer Res. , vol.48 , pp. 1494-1498
    • Ohno, Y.1    Spriggs, D.2    Matsukage, A.3    Ohno, T.4    Kufe, D.5
  • 29
    • 0026784943 scopus 로고
    • 3′-Azido-3′, 5′-dideoxythymidine-5′- methylphosphonic acid diphosphate: Synthesis and HIV-1 reverse transcriptase inhibition
    • Freeman, G. A.; Rideout, J. L.; Miller, W. H.; Reardon, J. E. 3′-Azido-3′, 5′-dideoxythymidine-5′-methylphosphonic acid diphosphate: Synthesis and HIV-1 reverse transcriptase inhibition. J. Med. Chem. 1992, 35, 3192-3196.
    • (1992) J. Med. Chem. , vol.35 , pp. 3192-3196
    • Freeman, G.A.1    Rideout, J.L.2    Miller, W.H.3    Reardon, J.E.4
  • 30
    • 0028069140 scopus 로고
    • Synthesis of 2′,3′,5′-trideoxyuridine-5′- methylphosphonic acid and its diphosphate derivative. Study of the interaction with HIV-1 reverse transcriptase
    • Benzaria, S.; Maury, G.; Gosselin, G.; Rittinger, K.; Divita, G.; Goody, R. S.; Imbach, J.-L. Synthesis of 2′,3′,5′-trideoxyuridine- 5′-methylphosphonic acid and its diphosphate derivative. Study of the interaction with HIV-1 reverse transcriptase. Antivir. Chem. Chemother. 1994, 5, 221-228.
    • (1994) Antivir. Chem. Chemother. , vol.5 , pp. 221-228
    • Benzaria, S.1    Maury, G.2    Gosselin, G.3    Rittinger, K.4    Divita, G.5    Goody, R.S.6    Imbach, J.-L.7
  • 31
    • 0033803374 scopus 로고    scopus 로고
    • Template/primer requirements and single nucleotide incorporation by hepatitis C virus nonstructural protein 5B polymerase
    • Zhong, W.; Ferrari, E.; Lesburg, C. A.; Maag, D.; Ghosh, S. K.; Cameron, C. E.; Lau, J. Y.; Hong, Z. Template/primer requirements and single nucleotide incorporation by hepatitis C virus nonstructural protein 5B polymerase. J. Virol. 2000, 74, 9134-9143.
    • (2000) J. Virol. , vol.74 , pp. 9134-9143
    • Zhong, W.1    Ferrari, E.2    Lesburg, C.A.3    Maag, D.4    Ghosh, S.K.5    Cameron, C.E.6    Lau, J.Y.7    Hong, Z.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.