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Volumn 35, Issue 8, 1992, Pages 1458-1465

Synthesis and Antiviral Activity of Acyclic Nucleosides with a 3(S),5-Dihydroxypentyl or 4(R)-Methoxy-3(S),5-dihydroxypentyl Side Chain

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXYRIBOSE; 9 (2,3 DIHYDROXYPROPYL)ADENINE; 9 (3 HYDROXYPROPOXY)GUANINE; 9 [3 HYDROXY 2 (HYDROXYMETHYL)PROPOXY]GUANINE; ACICLOVIR; ACYCLIC NUCLEOSIDE; BUCICLOVIR; GANCICLOVIR;

EID: 0026747732     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00086a015     Document Type: Article
Times cited : (50)

References (31)
  • 2
    • 0022532716 scopus 로고
    • Chemistry and Antiviral Activities of Acyclonucleosides
    • Chu, C. K.; Cutler, S. J. Chemistry and Antiviral Activities of Acyclonucleosides. J. Heterocycl. Chem. 1986, 23, 289-319.
    • (1986) J. Heterocycl. Chem. , vol.23 , pp. 289-319
    • Chu, C.K.1    Cutler, S.J.2
  • 3
    • 0020636893 scopus 로고
    • 9-[(1,3-Dihydroxy-2-propoxy)methyl]-guanine: A New Potent and Selective Antiherpes Agent
    • Martin, J. C.; Dvorak, C. A.; Smee, D. F.; Matthews, T. R.; Verheyden, J. P. H. 9-[(1,3-Dihydroxy-2-propoxy)methyl]-guanine: A New Potent and Selective Antiherpes Agent. J. Med. Chem. 1983, 26, 759-761.
    • (1983) J. Med. Chem. , vol.26 , pp. 759-761
    • Martin, J.C.1    Dvorak, C.A.2    Smee, D.F.3    Matthews, T.R.4    Verheyden, J.P.H.5
  • 4
    • 0020316367 scopus 로고
    • A New Nucleoside Analog, 9-[2-Hydroxy-l-(Hydroxymethyl)Ethoxy]-Methyl] Guanine, Highly Active In Vitro Against Herpes Simplex Virus Types 1 and 2
    • Smith, K. O.; Galloway, K. S.; Kennell, W. L.; Ogilvie, K. K.; Radatus, B. K. A New Nucleoside Analog, 9-[2-Hydroxy-l-(Hydroxymethyl)Ethoxy]-Methyl] Guanine, Highly Active In Vitro Against Herpes Simplex Virus Types 1 and 2. Antimicrob. Agents Chemother. 1982, 22, 55-61.
    • (1982) Antimicrob. Agents Chemother. , vol.22 , pp. 55-61
    • Smith, K.O.1    Galloway, K.S.2    Kennell, W.L.3    Ogilvie, K.K.4    Radatus, B.K.5
  • 6
    • 0018090383 scopus 로고
    • S)-9-(2,3-Dihydroxypropyl)adenine: An Aliphatic Nucleoside Analog with Broad-Spectrum Antiviral Activity
    • De Clercq, E.; Descamps, J.; De Somer, P.; Holý, A. (S)-9-(2,3-Dihydroxypropyl)adenine: An Aliphatic Nucleoside Analog with Broad-Spectrum Antiviral Activity. Science 1978, 200, 563-565.
    • (1978) Science , vol.200 , pp. 563-565
    • De Clercq, E.1    Descamps, J.2    De Somer, P.3    Holý, A.4
  • 7
    • 0021814903 scopus 로고
    • Synthesis and Antiherpetic Activity of (S)-,(R)-, and (±)-9-[(2,3-Dihydroxy-1 -propoxy)methyl]-guanine, Linear Isomers of 2′-Nor-2′-deoxyguanosine
    • Ashton, W. T.; Canning, L. F.; Reynolds, G. F.; Tolman, R. L.; Karkas, J. D.; Liou, R.; Davies, M-E. M.; DeWitt, C. M.; Perry, H. C.; Field, A. K. Synthesis and Antiherpetic Activity of (S)-,(R)-, and (±)-9-[(2,3-Dihydroxy-1 -propoxy)methyl]-guanine, Linear Isomers of 2′-Nor-2′-deoxyguanosine. J. Med. Chem. 1985,28, 926-933.
    • (1985) J. Med. Chem. , vol.28 , pp. 926-933
    • Ashton, W.T.1    Canning, L.F.2    Reynolds, G.F.3    Tolman, R.L.4    Karkas, J.D.5    Liou, R.6    Davies, M-E.M.7    DeWitt, C.M.8    Perry, H.C.9    Field, A.K.10
  • 9
    • 0025058715 scopus 로고
    • Synthesis and Antiviral Activity of 9-Alkoxypurines. 1. 9-(3-Hydroxypropoxy)-and 9-[3-Hydroxy-2-(hydroxymethyl)propoxyjpurines
    • Hamden, M. R.; Wyatt, P. G.; Boyd, M. R.; Sutton, D. Synthesis and Antiviral Activity of 9-Alkoxypurines. 1. 9-(3-Hydroxypropoxy)-and 9-[3-Hydroxy-2-(hydroxymethyl)propoxyjpurines. J. Med. Chem. 1990, 33, 187-196.
    • (1990) J. Med. Chem. , vol.33 , pp. 187-196
    • Hamden, M.R.1    Wyatt, P.G.2    Boyd, M.R.3    Sutton, D.4
  • 10
    • 0026023320 scopus 로고
    • Synthesis and Antiviral Activity of 9-Alkoxypurines. 2. 9-(2,3-Dihydroxypropoxy)-, (3,4-Dihydroxybutoxy)-, and 9-(1,4-Dihydroxybut-2-oxy)purines
    • Bailey, S.; Hamden, M. R.; Jarvest, R. L.; Parkin, A.; Boyd, M. R. Synthesis and Antiviral Activity of 9-Alkoxypurines. 2. 9-(2,3-Dihydroxypropoxy)-, (3,4-Dihydroxybutoxy)-, and 9-(1,4-Dihydroxybut-2-oxy)purines. J. Med. Chem. 1991, 34, 57-65.
    • (1991) J. Med. Chem. , vol.34 , pp. 57-65
    • Bailey, S.1    Hamden, M.R.2    Jarvest, R.L.3    Parkin, A.4    Boyd, M.R.5
  • 11
    • 0025195924 scopus 로고
    • Synthesis of New (±)-3,5-Dihydroxypentyl Nucleoside Analogues from l-Amino-5-(benzyloxy)pentan-3-ol and Their Antiviral Evaluation
    • Legraverend, M.; Boumchita, H.; Zerial, A.; Huel, C.; Lemaitre, M.; Bisagni, E. Synthesis of New (±)-3,5-Dihydroxypentyl Nucleoside Analogues from l-Amino-5-(benzyloxy)pentan-3-ol and Their Antiviral Evaluation. J. Med. Chem. 1990, 33, 2476-2480.
    • (1990) J. Med. Chem. , vol.33 , pp. 2476-2480
    • Legraverend, M.1    Boumchita, H.2    Zerial, A.3    Huel, C.4    Lemaitre, M.5    Bisagni, E.6
  • 12
    • 0018717251 scopus 로고
    • Antiviral Activity of Aliphatic Nucleoside Analogues: Structure-Function Relationship
    • De Clercq, E.; Holy, A. Antiviral Activity of Aliphatic Nucleoside Analogues: Structure-Function Relationship. J. Med. Chem. 1979, 22, 510-513.
    • (1979) J. Med. Chem. , vol.22 , pp. 510-513
    • De Clercq, E.1    Holy, A.2
  • 14
    • 0002880232 scopus 로고
    • Stereochemical Control as a Function of Protecting-group Participation in 2-Deoxy-Derythro-pentofuranosylnucleosides
    • Wierenga, W.; Skulnick, H. I. Stereochemical Control as a Function of Protecting-group Participation in 2-Deoxy-Derythro-pentofuranosylnucleosides. Carbohydr. Res. 1981, 90, 41-52.
    • (1981) Carbohydr. Res. , vol.90 , pp. 41-52
    • Wierenga, W.1    Skulnick, H.I.2
  • 15
    • 0344902741 scopus 로고
    • A New Method for the Deoxygenation of Secondary Alcohols
    • Barton, D. H. R.; McCombie, S. W. A New Method for the Deoxygenation of Secondary Alcohols. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.
    • (1975) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 1574-1585
    • Barton, D.H.R.1    McCombie, S.W.2
  • 16
    • 0020764119 scopus 로고
    • Nucleic Acid Related Compounds. 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversion of Ribonucleosides to 2′-Deoxynucleosides
    • Robins, M. J.; Wilson, J. S.; Hansske, F. Nucleic Acid Related Compounds. 42. A General Procedure for the Efficient Deoxygenation of Secondary Alcohols. Regiospecific and Stereoselective Conversion of Ribonucleosides to 2′-Deoxynucleosides. J. Am. Chem. Soc. 1983,105, 4059-4065.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 4059-4065
    • Robins, M.J.1    Wilson, J.S.2    Hansske, F.3
  • 17
    • 85021499987 scopus 로고
    • Whistler, R. L., BeMiller, J. N., Eds.; Academic Press: New York & London
    • Brimacombe, J. S. In Methods in Carbohydrate Chemistry; Whistler, R. L., BeMiller, J. N., Eds.; Academic Press: New York & London, 1972; Vol. VI, pp 376-378.
    • (1972) Methods in Carbohydrate Chemistry , vol.6 , pp. 378
    • Brimacombe, J.S.1
  • 18
    • 33947294347 scopus 로고
    • A Facile Synthesis of Methanesulfonate Esters
    • Crossland, R. K.; Servis, K. L. A Facile Synthesis of Methanesulfonate Esters. J. Org. Chem. 1970, 35, 3195-3196.
    • (1970) J. Org. Chem. , vol.35 , pp. 3195-3196
    • Crossland, R.K.1    Servis, K.L.2
  • 19
    • 0343878999 scopus 로고
    • Synthesis of 3-Amino-and 3-Azidoanalogs of 9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA)
    • Holý, A. Synthesis of 3-Amino-and 3-Azidoanalogs of 9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine (HPMPA). Collect. Czech. Chem. Commun. 1989, 54, 446-454.
    • (1989) Collect. Czech. Chem. Commun. , vol.54 , pp. 446-454
    • Holý, A.1
  • 21
    • 0023248316 scopus 로고
    • Synthesis and Biological Activity of Unsaturated Carboacyclic Purine Nucleoside Analogues
    • Haines, D. R.; Tseng, C. K. H.; Marquez, V. E. Synthesis and Biological Activity of Unsaturated Carboacyclic Purine Nucleoside Analogues. J. Med. Chem. 1987, 30, 943-947.
    • (1987) J. Med. Chem. , vol.30 , pp. 943-947
    • Haines, D.R.1    Tseng, C.K.H.2    Marquez, V.E.3
  • 22
    • 84986694082 scopus 로고
    • Synthesis of 4-Substituted 2-Aminopyrrolo[2,3-d]pyrimidine 2′,3′-Dideoxyribonucleosides
    • Seela, F.; Muth, H.-P. Synthesis of 4-Substituted 2-Aminopyrrolo[2,3-d]pyrimidine 2′,3′-Dideoxyribonucleosides. Liebigs Ann. Chem. 1990, 227-232.
    • (1990) Liebigs Ann. Chem. , pp. 227-232
    • Seela, F.1    Muth, H.-P.2
  • 25
    • 0024373015 scopus 로고
    • Synthesis and Antiviral Activity of the Nucleotide Analogue (S)-l-[3-Hydroxy-2-(phosphonylmethoxy)-propyljcytosine
    • Bronson, J. J.; Ghazzouli, I.; Hitchcock, M. J. M.; Webb, R. R.; Martin, J. C. Synthesis and Antiviral Activity of the Nucleotide Analogue (S)-l-[3-Hydroxy-2-(phosphonylmethoxy)-propyljcytosine. J. Med. Chem. 1989, 32, 1457-1463.
    • (1989) J. Med. Chem. , vol.32 , pp. 1457-1463
    • Bronson, J.J.1    Ghazzouli, I.2    Hitchcock, M.J.M.3    Webb, R.R.4    Martin, J.C.5
  • 26
    • 0019975382 scopus 로고
    • Nucleic Acid Related Compounds. 37. Convenient and High-yield Syntheses of N-[(2-Hydroxyethoxy)methyl] Heterocycles as “Acyclic Nucleoside” Analogues
    • Robins, M. J.; Hatfield, P. W. Nucleic Acid Related Compounds. 37. Convenient and High-yield Syntheses of N-[(2-Hydroxyethoxy)methyl] Heterocycles as “Acyclic Nucleoside” Analogues. Can. J. Chem. 1982, 60, 547-553.
    • (1982) Can. J. Chem. , vol.60 , pp. 547-553
    • Robins, M.J.1    Hatfield, P.W.2
  • 27
    • 33749004747 scopus 로고
    • The Role of Neighbouring Groups in Replacement Reactions. XXVII. 5-Methoxyl Participation in Some Solvolysis Reactions
    • Allred, E. L.; Winstein, S. The Role of Neighbouring Groups in Replacement Reactions. XXVII. 5-Methoxyl Participation in Some Solvolysis Reactions. J. Am. Chem. Soc. 1967, 89, 3991-3997.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 3991-3997
    • Allred, E.L.1    Winstein, S.2
  • 28
    • 0005872566 scopus 로고
    • 6-Methoxyl Participation and Ion Pairs in Some Solvolysis Reactions
    • Allred, E. L.; Winstein, S. 6-Methoxyl Participation and Ion Pairs in Some Solvolysis Reactions. J. Am. Chem. Soc. 1967, 89, 4012-4017.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 4012-4017
    • Allred, E.L.1    Winstein, S.2
  • 31
    • 0021627143 scopus 로고
    • The Relative Merits and Drawbacks of New Nucleoside Analogues with Clinical Potential
    • Öberg, B.; Johansson, N.-G. The Relative Merits and Drawbacks of New Nucleoside Analogues with Clinical Potential. J. Antimicrob. Chemother. 1984, 14 (Suppl. A), 5-26.
    • (1984) J. Antimicrob. Chemother. , vol.14 , pp. 5-26
    • Öberg, B.1    Johansson, N.-G.2


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