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Volumn , Issue , 2009, Pages 165-198

Synthesis and Biological Activity of Fluorinated Nucleosides

Author keywords

Antiviral fluorinated nucleoside analogues; Biological activity of fluorinated nucleosides and correlations with conformations; Fluorination with perfluoroalkanesulfonyl fluorides; Industrial synthesis of Fdd A; Introduction of fluorine atom(s) into drug candidate compounds; Syntheses and antiviral activities of FddA and FddG; Synthesis and biological activity of fluorinated nucleosides; Synthesis of nucleoside analogues bearing fluorine atom(s) in their sugar moieties

Indexed keywords


EID: 84889375451     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781444312096.ch7     Document Type: Chapter
Times cited : (7)

References (113)
  • 1
    • 0014672259 scopus 로고
    • Structure of nucleocidin. III. Revised structure
    • Morton, G. O., Lancaster, J. E., Van Lear, G. E., et al. (1969) Structure of nucleocidin. III. Revised structure. J. Am. Chem. Soc., 91, 1535-1537.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1535-1537
    • Morton, G.O.1    Lancaster, J.E.2    Van Lear, G.E.3
  • 2
    • 33745464490 scopus 로고
    • Fluorinated pyrimidines, a new class of tumour-inhibitory compound
    • Heidelberger, C., Chaudhuri, N. K., Danneberg, P., et al. (1957) Fluorinated pyrimidines, a new class of tumour-inhibitory compound. Nature, 179(4561), 663-666.
    • (1957) Nature , vol.179 , Issue.4561 , pp. 663-666
    • Heidelberger, C.1    Chaudhuri, N.K.2    Danneberg, P.3
  • 3
    • 0023935362 scopus 로고
    • Synthesis of 2-deoxy-2,2-difluoro-D-ribose and 2-deoxy-2,2-difluoro-D-ribofuranosyl nucleosides
    • Hertel, L. W., Kroin, J. S., Misner, J. W. and Tustin, J. M. (1988) Synthesis of 2-deoxy-2,2-difluoro-D-ribose and 2-deoxy-2,2-difluoro-D-ribofuranosyl nucleosides. J. Org. Chem., 53, 2406-2409.
    • (1988) J. Org. Chem. , vol.53 , pp. 2406-2409
    • Hertel, L.W.1    Kroin, J.S.2    Misner, J.W.3    Tustin, J.M.4
  • 4
    • 33749263031 scopus 로고    scopus 로고
    • Discovery and development of clofarabine: a nucleoside analogue for treating cancer
    • Bonate, P. L., Arthaud, L., Cantrell, W. R., Jr., et al. (2006) Discovery and development of clofarabine: a nucleoside analogue for treating cancer. Nat. Rev. Drug Discov., 5, 855-863.
    • (2006) Nat. Rev. Drug Discov. , vol.5 , pp. 855-863
    • Bonate, P.L.1    Arthaud, L.2    Cantrell Jr., W.R.3
  • 5
    • 33749515464 scopus 로고    scopus 로고
    • Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo
    • Korba, B. E., Furman, P. A. and Otto, M. J. (2006) Clevudine: a potent inhibitor of hepatitis B virus in vitro and in vivo. Expert Rev. Anti-Infect. Ther., 4, 549-561.
    • (2006) Expert Rev. Anti-Infect. Ther. , vol.4 , pp. 549-561
    • Korba, B.E.1    Furman, P.A.2    Otto, M.J.3
  • 9
    • 27944449177 scopus 로고    scopus 로고
    • Development of an industrial process for synthesizing lodenosine (FddA)
    • Takamatsu, S., Maruyama, T. and Izawa, K. (2005) Development of an industrial process for synthesizing lodenosine (FddA). Yuki Gosei Kagaku Kyokaishi, 63, 864-878.
    • (2005) Yuki Gosei Kagaku Kyokaishi , vol.63 , pp. 864-878
    • Takamatsu, S.1    Maruyama, T.2    Izawa, K.3
  • 11
    • 36749043821 scopus 로고    scopus 로고
    • The synthesis of an antiviral fluorinated purine nucleoside: 3' -a-fluoro-2',3'-dideoxyguanosine
    • ACS Symposium Series
    • Izawa, K., Torii, T., Onishi, T. and Maruyama, T. (2007) The synthesis of an antiviral fluorinated purine nucleoside: 3' -a-fluoro-2',3'-dideoxyguanosine. Current Fluoroorganic Chemistry, ACS Symposium Series 949, pp. 363-378.
    • (2007) Current Fluoroorganic Chemistry , vol.949 , pp. 363-378
    • Izawa, K.1    Torii, T.2    Onishi, T.3    Maruyama, T.4
  • 12
    • 0024580284 scopus 로고
    • Synthesis of nucleosides fluorinated in the sugar moiety. The application of diethylaminosulfur trifluoride to the synthesis of fluorinated nucleosides
    • Herdewijn, P., Van Aerschot, A. and Kerremans, L. (1989) Synthesis of nucleosides fluorinated in the sugar moiety. The application of diethylaminosulfur trifluoride to the synthesis of fluorinated nucleosides. Nucleosides Nucleotides, 8, 65-96.
    • (1989) Nucleosides Nucleotides , vol.8 , pp. 65-96
    • Herdewijn, P.1    Van Aerschot, A.2    Kerremans, L.3
  • 13
    • 0034631778 scopus 로고    scopus 로고
    • Fluorinated nucleosides
    • Pankeiwicz, K. W. (2000) Fluorinated nucleosides. Carbohydr. Res., 327, 87-105.
    • (2000) Carbohydr. Res. , vol.327 , pp. 87-105
    • Pankeiwicz, K.W.1
  • 14
    • 0010576797 scopus 로고
    • Synthesis of 2'-ß-fluoro-substituted nucleosides by a direct approach
    • Pankeiwicz, K. W. and Watanabe, K. A. (1993) Synthesis of 2'-ß-fluoro-substituted nucleosides by a direct approach. J. Fluorine Chem., 64, 15-36.
    • (1993) J. Fluorine Chem. , vol.64 , pp. 15-36
    • Pankeiwicz, K.W.1    Watanabe, K.A.2
  • 15
    • 0003458038 scopus 로고
    • Pronciples of Nucleic Acid Structure
    • Springer-Verlag, New York
    • Saenger, W. (1984) Pronciples of Nucleic Acid Structure. Springer-Verlag, New York.
    • (1984)
    • Saenger, W.1
  • 16
    • 0005220594 scopus 로고
    • Nucleoside. XVIII. Synthesis of 2'-fluorothymidine, 2'-fluorodeoxyuridine, and other 2'-halogeno-2'-deoxy nucleosides
    • Codington, J. F., Doerr, I. L. and Fox, J. J. (1964) Nucleoside. XVIII. Synthesis of 2'-fluorothymidine, 2'-fluorodeoxyuridine, and other 2'-halogeno-2'-deoxy nucleosides. J. Org. Chem., 29, 558-564.
    • (1964) J. Org. Chem. , vol.29 , pp. 558-564
    • Codington, J.F.1    Doerr, I.L.2    Fox, J.J.3
  • 17
    • 0016686131 scopus 로고
    • Nucleosides of fluorocarbohydrates. XIII. Synthesis of 3'-deoxy-3'-fluorouridine
    • Kowollik, G., Gaertner, K. and Langen, P. (1975) Nucleosides of fluorocarbohydrates. XIII. Synthesis of 3'-deoxy-3'-fluorouridine. J. Carbohydr., Nucleosides, Nucleotides, 2, 191-195.
    • (1975) J. Carbohydr., Nucleosides, Nucleotides , vol.2 , pp. 191-195
    • Kowollik, G.1    Gaertner, K.2    Langen, P.3
  • 18
    • 0021151896 scopus 로고
    • Reaction of 1-(2',3'-epoxy-ß-D-lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1-(3'-fluoro-3'-deoxy-ß-D-ribofuranosyl)uracil
    • Misra, H. K., Gati, W. P., Knaus, E. E. and Wiebe, L. I. (1984) Reaction of 1-(2',3'-epoxy-ß-D-lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1-(3'-fluoro-3'-deoxy-ß-D-ribofuranosyl)uracil. J. Heterocyclic Chem., 21, 773-775.
    • (1984) J. Heterocyclic Chem. , vol.21 , pp. 773-775
    • Misra, H.K.1    Gati, W.P.2    Knaus, E.E.3    Wiebe, L.I.4
  • 19
    • 85008138129 scopus 로고
    • Studies of nucleosides and nucleotides. LXIX. Purine cyclonucleosides. (30). Elimination of the 8-oxy function of purine nucleosides
    • Ikehara, M. and Maruyama, T. (1976) Studies of nucleosides and nucleotides. LXIX. Purine cyclonucleosides. (30). Elimination of the 8-oxy function of purine nucleosides. Chem. Pharm. Bull., 24, 565-569.
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 565-569
    • Ikehara, M.1    Maruyama, T.2
  • 20
    • 0017395396 scopus 로고
    • Studies of nucleosides and nucleotides. LXXXV. Purine cyclonucleosides. (35). Synthesis of purine nucleosides having 2'-azido and 2'-amino functions by cleavage of purine cyclonucleosides
    • Ikehara, M., Maruyama, T., Miki, H. and Takatsuka, Y. (1977) Studies of nucleosides and nucleotides. LXXXV. Purine cyclonucleosides. (35). Synthesis of purine nucleosides having 2'-azido and 2'-amino functions by cleavage of purine cyclonucleosides. Chem. Pharm. Bull., 25, 754-760.
    • (1977) Chem. Pharm. Bull. , vol.25 , pp. 754-760
    • Ikehara, M.1    Maruyama, T.2    Miki, H.3    Takatsuka, Y.4
  • 21
    • 0015966027 scopus 로고
    • Preparation and synthetic utility of some organotin derivatives of nucleosides
    • Wagner, J., Verheyden, J. P. H. and Moffatt, J. G. (1974) Preparation and synthetic utility of some organotin derivatives of nucleosides. J. Org. Chem., 39, 24-30.
    • (1974) J. Org. Chem. , vol.39 , pp. 24-30
    • Wagner, J.1    Verheyden, J.P.H.2    Moffatt, J.G.3
  • 22
    • 0016770241 scopus 로고
    • Studies of nucleosides and nucleotides-LXV: Purine cyclonucleosides-26 a versatile method for the synthesis of purine O- cyclo-nucleosides. The first synthesis of 8,2'-anhydro-8-oxy 9-ß-D-arabinofuranosylguanine
    • Ikehara, M. and Maruyama, T. (1975) Studies of nucleosides and nucleotides-LXV: Purine cyclonucleosides-26 a versatile method for the synthesis of purine O- cyclo-nucleosides. The first synthesis of 8,2'-anhydro-8-oxy 9-ß-D-arabinofuranosylguanine. Tetrahedron, 31, 1369-1372.
    • (1975) Tetrahedron , vol.31 , pp. 1369-1372
    • Ikehara, M.1    Maruyama, T.2
  • 23
    • 0011673222 scopus 로고
    • A new method for the synthesis of 2'-substi-tuted purine nucleosides. Total synthesis of an antibiotic 2' -amino-2'-deoxyguanosine
    • Ikehara, M., Maruyama, T. and Miki, H. (1976) A new method for the synthesis of 2'-substi-tuted purine nucleosides. Total synthesis of an antibiotic 2' -amino-2'-deoxyguanosine. Tetrahedron Lett., 17, 4485-1488.
    • (1976) Tetrahedron Lett. , vol.17 , pp. 4485-1488
    • Ikehara, M.1    Maruyama, T.2    Miki, H.3
  • 24
    • 84998356001 scopus 로고
    • Studies of Nucleosides and Nucleotides. LXXXII. Cyclonu-cleosides. (39). Synthesis and Properties of 2'-Halogeno-2'-deoxyadenosines
    • Ikehara, M. and Miki, H. (1978) Studies of Nucleosides and Nucleotides. LXXXII. Cyclonu-cleosides. (39). Synthesis and Properties of 2'-Halogeno-2'-deoxyadenosines. Chem. Pharm. Bull., 26, 2449-2453.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 2449-2453
    • Ikehara, M.1    Miki, H.2
  • 25
    • 85010140332 scopus 로고
    • Studies on nucleosides and nucleotides. LXXXVII. Purine cyclonucleosides. XLII. Synthesis of 2'-deoxy-2'-fluoroguanosine
    • Ikehara, M. and Imura, J. (1981) Studies on nucleosides and nucleotides. LXXXVII. Purine cyclonucleosides. XLII. Synthesis of 2'-deoxy-2'-fluoroguanosine. Chem. Pharm. Bull., 29, 1034-1038.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 1034-1038
    • Ikehara, M.1    Imura, J.2
  • 26
    • 0002247784 scopus 로고
    • Modification of the 2'-position of purine nucleosides: syntheses of 2'-a-substituted-2'-deoxyadenosine analogs
    • Ranganathan, R. (1977) Modification of the 2'-position of purine nucleosides: syntheses of 2'-a-substituted-2'-deoxyadenosine analogs. Tetrahedron Lett., 18, 1291-1294.
    • (1977) Tetrahedron Lett. , vol.18 , pp. 1291-1294
    • Ranganathan, R.1
  • 27
    • 0003851633 scopus 로고
    • Protective Groups in Organic Chemistry
    • Plenum Press, New York
    • McOmie, J. F. W. (1973) Protective Groups in Organic Chemistry. Plenum Press, New York.
    • (1973)
    • McOmie, J.F.W.1
  • 28
    • 16444368755 scopus 로고
    • Regioselective protection of carbohydrate derivatives. Part 20. Simple, efficient 2'-O-deacylation of fully acylated purine and pyrimidine ribonucleosides through tert-butoxide
    • Nishino, S., Takamura, H. and Ishido, Y. (1986) Regioselective protection of carbohydrate derivatives. Part 20. Simple, efficient 2'-O-deacylation of fully acylated purine and pyrimidine ribonucleosides through tert-butoxide. Tetrahedron, 42, 1995-2004.
    • (1986) Tetrahedron , vol.42 , pp. 1995-2004
    • Nishino, S.1    Takamura, H.2    Ishido, Y.3
  • 29
    • 84959833747 scopus 로고
    • A new type of silyl protecting groups in nucleoside chemistry
    • Markiewicz, W. T. and Wiewiorowski, M. (1978) A new type of silyl protecting groups in nucleoside chemistry. Nucleic Acids Res., Spec. Publ., 4, 185-188.
    • (1978) Nucleic Acids Res., Spec. Publ. , vol.4 , pp. 185-188
    • Markiewicz, W.T.1    Wiewiorowski, M.2
  • 30
    • 0002515730 scopus 로고
    • Tetraisopropyldisiloxane-1,3-diyl, a group for simultaneous protection of 3-and 5 -hydroxy functions of nucleosides
    • Markiewicz, W. T. (1975) Tetraisopropyldisiloxane-1,3-diyl, a group for simultaneous protection of 3-and 5 -hydroxy functions of nucleosides. J. Chem. Res., Synopses, 24-25.
    • (1975) J. Chem. Res., Synopses , pp. 24-25
    • Markiewicz, W.T.1
  • 31
    • 0028300310 scopus 로고
    • Synthesis and anti-HIV activity of 6-substituted purine 2'-deoxy-2'-fluororibosides
    • Maruyama, T., Utzumi, K., Sato, Y. and Richman, D. D. (1994) Synthesis and anti-HIV activity of 6-substituted purine 2'-deoxy-2'-fluororibosides. Nucleosides Nucleotides, 13, 527-537.
    • (1994) Nucleosides Nucleotides , vol.13 , pp. 527-537
    • Maruyama, T.1    Utzumi, K.2    Sato, Y.3    Richman, D.D.4
  • 32
    • 0028339403 scopus 로고
    • Synthesis and anti-HIV activity of 2-substituted 2'-deoxy-2'-fluoroadenosines
    • Maruyama, T., Utzumi, K., Sato, Y. and Richman, D. D. (1994) Synthesis and anti-HIV activity of 2-substituted 2'-deoxy-2'-fluoroadenosines. Nucleosides Nucleotides, 13, 1219-1230.
    • (1994) Nucleosides Nucleotides , vol.13 , pp. 1219-1230
    • Maruyama, T.1    Utzumi, K.2    Sato, Y.3    Richman, D.D.4
  • 33
    • 0003586747 scopus 로고
    • Nucleosides as Biological Probes
    • John Wiley and Sons, Inc., New York
    • Suhadolnik, R. J. (1979) Nucleosides as Biological Probes. John Wiley and Sons, Inc., New York, pp. 96-102.
    • (1979) , pp. 96-102
    • Suhadolnik, R.J.1
  • 34
    • 0029005020 scopus 로고
    • Synthesis, antiviral, antibacterial and antitumor cell activities of 2'-deoxy-2'-fluoropuromycin
    • Maruyama, T., Utsumi, K., Tomioka, H., et al. (1995) Synthesis, antiviral, antibacterial and antitumor cell activities of 2'-deoxy-2'-fluoropuromycin. Chem. Pharm. Bull., 43, 955-959.
    • (1995) Chem. Pharm. Bull. , vol.43 , pp. 955-959
    • Maruyama, T.1    Utsumi, K.2    Tomioka, H.3
  • 35
    • 0025669786 scopus 로고
    • Synthesis and antimicrobial activity of 2 -deoxypuromycin
    • Koizumi, F., Oritani, T. and Yamashita, K. (1990) Synthesis and antimicrobial activity of 2 -deoxypuromycin. Agric. Biol. Chem., 54, 3093-3097.
    • (1990) Agric. Biol. Chem. , vol.54 , pp. 3093-3097
    • Koizumi, F.1    Oritani, T.2    Yamashita, K.3
  • 36
    • 0012198368 scopus 로고
    • The effect of ribonuclease on the cells of the Ehrlich carcinoma
    • Ledoux, L. and Baltus, E. (1954) The effect of ribonuclease on the cells of the Ehrlich carcinoma. Experientia, 10, 500-501.
    • (1954) Experientia , vol.10 , pp. 500-501
    • Ledoux, L.1    Baltus, E.2
  • 37
    • 0003894111 scopus 로고    scopus 로고
    • Ribonucleases: Structures and Functions
    • Academic Press, New York
    • Youle, R. J. and D'Alessio, G. (1997) Ribonucleases: Structures and Functions. Academic Press, New York, pp. 491-514.
    • (1997) , pp. 491-514
    • Youle, R.J.1    D'Alessio, G.2
  • 38
    • 0027515122 scopus 로고
    • Crystal structure of ribonuclease Ms (as a ribonuclease T1 homolog) complexed with a guanylyl- 3,5-cytidine analog
    • Nonaka, T., Nakamura, K. T., Uesugi, S., et al. (1993) Crystal structure of ribonuclease Ms (as a ribonuclease T1 homolog) complexed with a guanylyl- 3,5-cytidine analog. Biochemistry, 32, 11825-11837.
    • (1993) Biochemistry , vol.32 , pp. 11825-11837
    • Nonaka, T.1    Nakamura, K.T.2    Uesugi, S.3
  • 39
    • 0019767856 scopus 로고
    • Studies on nucleosides and nucleotides. LXXXIX. Purine cyclonucleosides. (43). Synthesis and properties of 2-halogeno-2-deoxyguanosines
    • Ikehara, M. and Imura, J. (1981) Studies on nucleosides and nucleotides. LXXXIX. Purine cyclonucleosides. (43). Synthesis and properties of 2-halogeno-2-deoxyguanosines. Chem. Pharm. Bull., 29, 3281-3285.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 3281-3285
    • Ikehara, M.1    Imura, J.2
  • 40
    • 0026751642 scopus 로고
    • Synthesis of suitably-protected phosphoramidites of 2'-fluoro-2'-deoxyguanosine and 2'-amino-2'-deoxyguanosine for incorporation into oligoribonucleotides
    • Benseler, F., Williams, D. M. and Eckstein, F. (1992) Synthesis of suitably-protected phosphoramidites of 2'-fluoro-2'-deoxyguanosine and 2'-amino-2'-deoxyguanosine for incorporation into oligoribonucleotides. Nucleosides, Nucleotides, Nucleic Acids, 11, 1333-1351.
    • (1992) Nucleosides, Nucleotides, Nucleic Acids , vol.11 , pp. 1333-1351
    • Benseler, F.1    Williams, D.M.2    Eckstein, F.3
  • 42
    • 0021177067 scopus 로고
    • Uridine as an active component of sleep-promoting substance: its effects on nocturnal sleep in rats
    • Honda, K., Komoda, Y., Nishida, S., et al. (1984) Uridine as an active component of sleep-promoting substance: its effects on nocturnal sleep in rats. Neurosci. Res., 1, 243-252.
    • (1984) Neurosci. Res. , vol.1 , pp. 243-252
    • Honda, K.1    Komoda, Y.2    Nishida, S.3
  • 43
    • 0023618909 scopus 로고
    • N-Substituted oxopyrimidines and nucleo-sides: structure-activity relationship for hypnotic activity as CNS depressant
    • Yamamoto, I., Kimura, T., Takeoka, Y., et al. (1987) N-Substituted oxopyrimidines and nucleo-sides: structure-activity relationship for hypnotic activity as CNS depressant. J. Med. Chem., 30, 2227-2231.
    • (1987) J. Med. Chem. , vol.30 , pp. 2227-2231
    • Yamamoto, I.1    Kimura, T.2    Takeoka, Y.3
  • 44
    • 0028365224 scopus 로고
    • Synthesis and hypnotic and anti-human immunodeficiency virus-1 activities of N3-Substituted 2'-Deoxy-2'-fluorouridines
    • Sato, Y., Utsumi, K., Maruyama, T., et al. (1994) Synthesis and hypnotic and anti-human immunodeficiency virus-1 activities of N3-Substituted 2'-Deoxy-2'-fluorouridines. Chem. Pharm. Bull., 42, 595-598.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 595-598
    • Sato, Y.1    Utsumi, K.2    Maruyama, T.3
  • 45
    • 0042922008 scopus 로고
    • Nucleosides. CXLIII. Synthesis of 5'-deoxy-5-substituted-2,2-anhydro-1-(ß -D- arabinofuranosyl)uracils. A new 2,5-to 2,2-anhydronucle-oside transformation. Studies directed toward the synthesis of 2-deoxy-2-substituted arabino nucleosides. (4)
    • Pankiewicz, K. W. and Watanabe, K. A. (1987) Nucleosides. CXLIII. Synthesis of 5'-deoxy-5-substituted-2,2-anhydro-1-(ß -D- arabinofuranosyl)uracils. A new 2,5-to 2,2-anhydronucle-oside transformation. Studies directed toward the synthesis of 2-deoxy-2-substituted arabino nucleosides. (4). Chem. Pharm. Bull., 35, 4494-4497.
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 4494-4497
    • Pankiewicz, K.W.1    Watanabe, K.A.2
  • 46
    • 0024307897 scopus 로고
    • Anew method for synthesizing the antineoplastic nucleosides 1- (2-azido-2-deoxy -ß -D- arabinofuranosyl)cytosine (Cytarazid) and 1- (2-amino-2 -deoxy -ß -D- arabinofuranosyl)cytosine (Cytaramin) from uridine
    • Matsuda, A., Yasuoka, J. and Ueda, T. (1989) Anew method for synthesizing the antineoplastic nucleosides 1- (2-azido-2-deoxy -ß -D- arabinofuranosyl)cytosine (Cytarazid) and 1- (2-amino-2 -deoxy -ß -D- arabinofuranosyl)cytosine (Cytaramin) from uridine. Chem. Pharm. Bull., 37, 1659-1661.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1659-1661
    • Matsuda, A.1    Yasuoka, J.2    Ueda, T.3
  • 47
    • 0026540845 scopus 로고
    • A synthesis of 9-(2-deoxy-2-fluoro-ß -D-arabinofuranosyl)adenine and -hypoxanthine. An effect of C3'-endo to C2'-endo conformational shift on the reaction course of 2' -hydroxyl group with DAST
    • Pankiewicz, K. W., Krzeminski, J., Ciszewski, L. A., et al. (1992) A synthesis of 9-(2-deoxy-2-fluoro-ß -D-arabinofuranosyl)adenine and -hypoxanthine. An effect of C3'-endo to C2'-endo conformational shift on the reaction course of 2' -hydroxyl group with DAST. J. Org. Chem., 57, 553-559.
    • (1992) J. Org. Chem. , vol.57 , pp. 553-559
    • Pankiewicz, K.W.1    Krzeminski, J.2    Ciszewski, L.A.3
  • 48
    • 0025884618 scopus 로고
    • Synthesis of 9-(2-deoxy-2-fluoro-ß-D-arabinofuranosyl)hypoxanthine. The first direct introduction of a 2'-ß-fluoro substituent in preformed purine nucleosides. Studies directed toward the synthesis of 2' -deoxy-2'-substituted arabinonucleosides. 8
    • Krzeminski, J., Nawrot, B., Pankiewicz, K. W. and Watanabe, K. A. (1991) Synthesis of 9-(2-deoxy-2-fluoro-ß-D-arabinofuranosyl)hypoxanthine. The first direct introduction of a 2'-ß-fluoro substituent in preformed purine nucleosides. Studies directed toward the synthesis of 2' -deoxy-2'-substituted arabinonucleosides. 8. Nucleosides Nucleotides, 10, 781-798.
    • (1991) Nucleosides Nucleotides , vol.10 , pp. 781-798
    • Krzeminski, J.1    Nawrot, B.2    Pankiewicz, K.W.3    Watanabe, K.A.4
  • 49
    • 0030475181 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of 6-chloropurine arabinoside and its 2' -deoxy-2'-fluoro derivative
    • Maruyama, T., Sato, Y., Oto, Y., et al. (1996) Synthesis and antiviral activity of 6-chloropurine arabinoside and its 2' -deoxy-2'-fluoro derivative. Chem. Pharm. Bull., 44, 2331-2334.
    • (1996) Chem. Pharm. Bull. , vol.44 , pp. 2331-2334
    • Maruyama, T.1    Sato, Y.2    Oto, Y.3
  • 50
    • 0001619710 scopus 로고
    • A linear relationship between electronegativity of 2 -substituents and conformation of adenine nucleosides
    • Uesugi, S., Miki, H., Ikehara, M., et al. (1979) A linear relationship between electronegativity of 2 -substituents and conformation of adenine nucleosides. Tetrahedron Lett., 20, 4073-4076.
    • (1979) Tetrahedron Lett. , vol.20 , pp. 4073-4076
    • Uesugi, S.1    Miki, H.2    Ikehara, M.3
  • 51
    • 0032802071 scopus 로고    scopus 로고
    • Synthesis of 9-(2-deoxy-2-fluoro-ß-D-arabinofuranosyl)adenine bearing a selectively removable protecting group
    • Maruyama, T., Takamatsu, S., Kozai, S., et al. (1999) Synthesis of 9-(2-deoxy-2-fluoro-ß-D-arabinofuranosyl)adenine bearing a selectively removable protecting group. Chem. Pharm. Bull., 47, 966-970.
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 966-970
    • Maruyama, T.1    Takamatsu, S.2    Kozai, S.3
  • 52
    • 0032568223 scopus 로고    scopus 로고
    • A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (ß-FddA). Introduction of a 2'-ß-fluoro substituent via inversion of a readily obtainable 2'-a-fluoro isomer
    • Siddiqui, M. A., Driscoll, J. S. and Marquez, V. E. (1998) A new synthetic approach to the clinically useful, anti-HIV-active nucleoside, 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (ß-FddA). Introduction of a 2'-ß-fluoro substituent via inversion of a readily obtainable 2'-a-fluoro isomer. Tetrahedron Lett., 39, 1657-1660.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1657-1660
    • Siddiqui, M.A.1    Driscoll, J.S.2    Marquez, V.E.3
  • 53
    • 0023203860 scopus 로고
    • 2',3'-Dideoxy-2'-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV)
    • Marquez, V. E., Tseng, C. K.-H., Kelley, J. A., et al. (1987) 2',3'-Dideoxy-2'-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV). Biochem. Pharmacol., 36, 2719-2722.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2719-2722
    • Marquez, V.E.1    Tseng, C.K.-H.2    Kelley, J.A.3
  • 54
    • 0025218997 scopus 로고
    • Acid-stable 2'-fluoro purine dide-oxynucleosides as active agents against HIV
    • Marquez, V. E., Tseng, C. K.-H., Mitsuya, H., et al. (1990) Acid-stable 2'-fluoro purine dide-oxynucleosides as active agents against HIV. J. Med. Chem., 33, 978-985.
    • (1990) J. Med. Chem. , vol.33 , pp. 978-985
    • Marquez, V.E.1    Tseng, C.K.-H.2    Mitsuya, H.3
  • 55
    • 0029816732 scopus 로고    scopus 로고
    • Potent activity of 2'-ß-fluoro-2',3'-dideoxyadenosine against human immunodeficiency virus type 1 infection in hu-PBL-SCID mice
    • Ruxrungtham, K., Boone, E. B., Ford, H., Jr., et al. (1996) Potent activity of 2'-ß-fluoro-2',3'-dideoxyadenosine against human immunodeficiency virus type 1 infection in hu-PBL-SCID mice. Antimicrob. Agents Chemother., 40, 2369-2374.
    • (1996) Antimicrob. Agents Chemother. , vol.40 , pp. 2369-2374
    • Ruxrungtham, K.1    Boone, E.B.2    Ford Jr., H.3
  • 56
    • 0032445699 scopus 로고    scopus 로고
    • Lodenosine: anti-HIV (reverse transcriptase inhibitor)
    • Graul, A., Silvestre, J. and Castaner, J. (1998) Lodenosine: anti-HIV (reverse transcriptase inhibitor). Drugs Future, 23, 1176-1189.
    • (1998) Drugs Future , vol.23 , pp. 1176-1189
    • Graul, A.1    Silvestre, J.2    Castaner, J.3
  • 57
    • 0031057088 scopus 로고    scopus 로고
    • 2'-Fluoro-2',3'-dideoxyarabinosylade-nine (F-ddA): activity against drug-resistant human immunodeficiency virus strains and clades A-E
    • Driscoll, J. S., Mayers, D. L., Bader, J. P., et al. (1997) 2'-Fluoro-2',3'-dideoxyarabinosylade-nine (F-ddA): activity against drug-resistant human immunodeficiency virus strains and clades A-E. Antivir. Chem. Chemother., 8, 107-111.
    • (1997) Antivir. Chem. Chemother. , vol.8 , pp. 107-111
    • Driscoll, J.S.1    Mayers, D.L.2    Bader, J.P.3
  • 58
    • 0031009294 scopus 로고    scopus 로고
    • In vitro induction of human immunodeficiency virus type 1 variants resistant to 2'-ß-fluoro-2',3'-dideoxyadenosine
    • Tanaka, M, Srinivas, R. V., Ueno, T., et al. (1997) In vitro induction of human immunodeficiency virus type 1 variants resistant to 2'-ß-fluoro-2',3'-dideoxyadenosine. Antimicrob. Agents Chemother., 41, 1313-1318.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 1313-1318
    • Tanaka, M.1    Srinivas, R.V.2    Ueno, T.3
  • 59
    • 0030929865 scopus 로고    scopus 로고
    • Role of brain tissue localized purine metabolizing enzymes in the central nervous system delivery of anti-HIV agents 2 -ß -fluoro-2',3'-dideoxyinosine and 2'-ß-fluoro-2',3'-dideoxy-adenosine in rats
    • Singhal, D., Morgan, M. E. and Anderson, B. D. (1997) Role of brain tissue localized purine metabolizing enzymes in the central nervous system delivery of anti-HIV agents 2 -ß -fluoro-2',3'-dideoxyinosine and 2'-ß-fluoro-2',3'-dideoxy-adenosine in rats. Pharmaceutical Res., 14, 786-792.
    • (1997) Pharmaceutical Res. , vol.14 , pp. 786-792
    • Singhal, D.1    Morgan, M.E.2    Anderson, B.D.3
  • 60
    • 0029975891 scopus 로고    scopus 로고
    • Lipophilic, acid-stable, adenosine deaminase-activated anti-hiv prodrugs for central nervous system delivery. 3. 6-Amino pro-drugs of 2'-ß-fluoro-2',3'-dideoxyinosine
    • Driscoll, J. S., Siddiqui, M. A., Ford, H., Jr., et al. (1996) Lipophilic, acid-stable, adenosine deaminase-activated anti-hiv prodrugs for central nervous system delivery. 3. 6-Amino pro-drugs of 2'-ß-fluoro-2',3'-dideoxyinosine. J. Med. Chem., 39, 1619-1625.
    • (1996) J. Med. Chem. , vol.39 , pp. 1619-1625
    • Driscoll, J.S.1    Siddiqui, M.A.2    Ford Jr., H.3
  • 61
    • 0030457859 scopus 로고    scopus 로고
    • Localization of purine metabolizing enzymes in bovine brain microvessel endothelial cells: an enzymic blood-brain barrier for dideoxynucleo-sides?
    • Johnson, M. D. and Anderson, B. D. (1996) Localization of purine metabolizing enzymes in bovine brain microvessel endothelial cells: an enzymic blood-brain barrier for dideoxynucleo-sides? Pharm. Res., 13, 1881-1886.
    • (1996) Pharm. Res. , vol.13 , pp. 1881-1886
    • Johnson, M.D.1    Anderson, B.D.2
  • 62
    • 0028905177 scopus 로고
    • Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 2. 6-Halo-and 6 -alkoxy prodrugs of 2'-ß-fluoro-2',3'-dideoxyinosine
    • Ford, H., Jr., Siddiqui, M., Driscoll, J. S., et al. (1995) Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 2. 6-Halo-and 6 -alkoxy prodrugs of 2'-ß-fluoro-2',3'-dideoxyinosine. J. Med. Chem., 38, 1189-1195.
    • (1995) J. Med. Chem. , vol.38 , pp. 1189-1195
    • Ford Jr., H.1    Siddiqui, M.2    Driscoll, J.S.3
  • 63
    • 0036150259 scopus 로고    scopus 로고
    • Investigation of the mechanism of enhancement of central nervous system delivery of 2'-ß-fluoro-2',3'-dideoxyinosine via a blood-brain barrier adenosine deaminase-activated prodrug
    • Johnson, M. D., Chen, J. and Anderson, B. D. (2002) Investigation of the mechanism of enhancement of central nervous system delivery of 2'-ß-fluoro-2',3'-dideoxyinosine via a blood-brain barrier adenosine deaminase-activated prodrug. Drug Metab. Dispos., 30, 191-198.
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 191-198
    • Johnson, M.D.1    Chen, J.2    Anderson, B.D.3
  • 64
    • 0023551961 scopus 로고
    • Synthesis and anti-HIV activity of various 2-and 3-substituted 2,3-dideoxyadenosines: a structure- activity analysis
    • Herdewijn, P., Pauwels, R., Baba, M., et al. (1987) Synthesis and anti-HIV activity of various 2-and 3-substituted 2,3-dideoxyadenosines: a structure- activity analysis. J. Med. Chem., 20, 2131-2137.
    • (1987) J. Med. Chem. , vol.20 , pp. 2131-2137
    • Herdewijn, P.1    Pauwels, R.2    Baba, M.3
  • 65
    • 2742614264 scopus 로고
    • Design, synthesis, and antiviral activity of nucleoside and nucleotide analogs
    • ACS Symposium Series
    • Marquez, V. E. (1989) Design, synthesis, and antiviral activity of nucleoside and nucleotide analogs. Nucleotide Analogues Antiviral Agents, ACS Symposium Series 401, pp. 140-155.
    • (1989) Nucleotide Analogues Antiviral Agents , vol.401 , pp. 140-155
    • Marquez, V.E.1
  • 66
    • 0026055397 scopus 로고
    • A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl nucleosides
    • Wysocki, R. J., Jr., Siddiqui, M. A., Barchi, J. J., Jr., et al. (1991) A more expedient approach to the synthesis of anti-HIV-active 2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl nucleosides. Synthesis, 1005-1008.
    • (1991) Synthesis , pp. 1005-1008
    • Wysocki Jr., R.J.1    Siddiqui, M.A.2    Barchi Jr., J.J.3
  • 67
    • 0028229018 scopus 로고
    • A diastereo-selective synthesis of (S,S)-a-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester, a key intermediate for the preparation of anti-HIV effective fluorodideoxy nucleosides
    • Siddiqui, M. A., Marquez, V. E., Driscoll, J. S. and Barchi, J. J., Jr. (1994) A diastereo-selective synthesis of (S,S)-a-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester, a key intermediate for the preparation of anti-HIV effective fluorodideoxy nucleosides. Tetrahedron Lett., 35, 3263-3266.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3263-3266
    • Siddiqui, M.A.1    Marquez, V.E.2    Driscoll, J.S.3    Barchi Jr., J.J.4
  • 68
    • 0034096656 scopus 로고    scopus 로고
    • The "ß-fluorine effect" in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates
    • Siddiqui, M. A., Driscoll, J. S., Abushanab, E., et al. (2000) The "ß-fluorine effect" in the non-metal hydride radical deoxygenation of fluorine-containing nucleoside xanthates. Nucleosides, Nucleotides, Nucleic Acids, 19, 1-12.
    • (2000) Nucleosides, Nucleotides, Nucleic Acids , vol.19 , pp. 1-12
    • Siddiqui, M.A.1    Driscoll, J.S.2    Abushanab, E.3
  • 69
    • 0346157339 scopus 로고    scopus 로고
    • A new synthetic approach to 2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranose, the fluorofuranose unit of the anti-HIV-active nucleoside, ß-FddA
    • Caille, J.-C., Miel, H., Armstrong, P. and McKervey, M. A. (2004) A new synthetic approach to 2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranose, the fluorofuranose unit of the anti-HIV-active nucleoside, ß-FddA. Tetrahedron Lett., 45, 863-865.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 863-865
    • Caille, J.-C.1    Miel, H.2    Armstrong, P.3    McKervey, M.A.4
  • 70
    • 0028214975 scopus 로고
    • Enhanced brain delivery of an anti-HIV nucleoside 2-F-ara-ddI by xanthine oxidase mediated biotransformation
    • Shanmuganathan, K., Koudriakova, T., Nampalli, S., et al. (1994) Enhanced brain delivery of an anti-HIV nucleoside 2-F-ara-ddI by xanthine oxidase mediated biotransformation. J. Med. Chem., 37, 821-827.
    • (1994) J. Med. Chem. , vol.37 , pp. 821-827
    • Shanmuganathan, K.1    Koudriakova, T.2    Nampalli, S.3
  • 71
    • 0035898740 scopus 로고    scopus 로고
    • (2R,3S,5S)-2-Acetoxy-3-fluoro-5-(p-toluoy-loxymethyl) tetrahydrofuran: a key intermediate for the practical synthesis of 9- (2,3-dideoxy -2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA)
    • Jin, F., Wang, D., Confalone, P. N., et al. (2001) (2R,3S,5S)-2-Acetoxy-3-fluoro-5-(p-toluoy-loxymethyl) tetrahydrofuran: a key intermediate for the practical synthesis of 9- (2,3-dideoxy -2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA). Tetrahedron Lett., 42, 4787-4789.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4787-4789
    • Jin, F.1    Wang, D.2    Confalone, P.N.3
  • 72
    • 0037421093 scopus 로고    scopus 로고
    • A concise synthesis of anti- viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone
    • Choudhury, A., Jin, F., Wang, D., et al. (2003) A concise synthesis of anti- viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone. Tetrahedron Lett., 44, 247-250.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 247-250
    • Choudhury, A.1    Jin, F.2    Wang, D.3
  • 73
    • 0035906076 scopus 로고    scopus 로고
    • Improved synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA) using triethylamine trihydrofluo-ride
    • Takamatsu, S., Maruyama, T., Katayama, S., et al. (2001) Improved synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA) using triethylamine trihydrofluo-ride. Tetrahedron Lett., 42, 2321-2324.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2321-2324
    • Takamatsu, S.1    Maruyama, T.2    Katayama, S.3
  • 74
    • 33751385486 scopus 로고
    • The invention of radical reactions. Part 32. Radical deoxygenations, dehalogenations, and deaminations with dialkyl phosphites and hypophosphorous acid as hydrogen sources
    • Barton, D. H. R., Jang, D. O. and Jaszberenyi, J. C. (1993) The invention of radical reactions. Part 32. Radical deoxygenations, dehalogenations, and deaminations with dialkyl phosphites and hypophosphorous acid as hydrogen sources. J. Org. Chem., 58, 6838-6842.
    • (1993) J. Org. Chem. , vol.58 , pp. 6838-6842
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.C.3
  • 75
    • 0035935141 scopus 로고    scopus 로고
    • Radical deoxygenation and dehalogena-tion of nucleoside derivatives with hypophosphorous acid and dialkyl phosphites
    • Takamatsu, S., Katayama, S., Hirose, N., et al. (2001) Radical deoxygenation and dehalogena-tion of nucleoside derivatives with hypophosphorous acid and dialkyl phosphites. Tetrahedron Lett., 42, 7605-7608.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 7605-7608
    • Takamatsu, S.1    Katayama, S.2    Hirose, N.3
  • 76
    • 0026535656 scopus 로고
    • A novel method for the synthesis of ddA and F-ddA via regioselective 2' -O-deacetylation of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-ß-D-xylofuranosyl)adenine
    • Shiragami, H., Tanaka, Y., Uchida, Y., et al. (1992) A novel method for the synthesis of ddA and F-ddA via regioselective 2' -O-deacetylation of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-ß-D-xylofuranosyl)adenine. Nucleosides Nucleotides, 11, 391-100.
    • (1992) Nucleosides Nucleotides , vol.11 , pp. 391-100
    • Shiragami, H.1    Tanaka, Y.2    Uchida, Y.3
  • 77
    • 0029935558 scopus 로고    scopus 로고
    • Synthesis of 2',3'-dideoxypurinenucleosides via the palladium catalyzed reduction of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-ß-D-xylofuranosyl)purine derivatives
    • Shiragami, H., Amino, Y., Honda, Y., et al. (1996) Synthesis of 2',3'-dideoxypurinenucleosides via the palladium catalyzed reduction of 9-(2,5-di-O-acetyl-3-bromo-3-deoxy-ß-D-xylofuranosyl)purine derivatives. Nucleosides Nucleotides, 15, 31-15.
    • (1996) Nucleosides Nucleotides , vol.15 , pp. 31-15
    • Shiragami, H.1    Amino, Y.2    Honda, Y.3
  • 78
    • 0035906074 scopus 로고    scopus 로고
    • Practical synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl) adenine (FddA) via a purine 3'-deoxynucleoside
    • Takamatsu, S., Maruyama, T., Katayama, S., et al. (2001) Practical synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl) adenine (FddA) via a purine 3'-deoxynucleoside. Tetrahedron Lett., 42, 2325-2328.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2325-2328
    • Takamatsu, S.1    Maruyama, T.2    Katayama, S.3
  • 79
    • 0035798042 scopus 로고    scopus 로고
    • Synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA) via a purine 3' -deoxynucleoside
    • Takamatsu, S., Maruyama, T., Katayama, S., et al. (2001) Synthesis of 9-(2,3-dideoxy-2-fluoro-ß-D-threo-pentofuranosyl)adenine (FddA) via a purine 3' -deoxynucleoside. J. Org. Chem., 66, 7469-7477.
    • (2001) J. Org. Chem. , vol.66 , pp. 7469-7477
    • Takamatsu, S.1    Maruyama, T.2    Katayama, S.3
  • 80
    • 0036918573 scopus 로고    scopus 로고
    • Convenient synthesis of fluorinated nucleosides with perfluoroalkanesulfonyl fluorides
    • Takamatsu, S., Katayama, S., Hirose, N., et al. (2002) Convenient synthesis of fluorinated nucleosides with perfluoroalkanesulfonyl fluorides. Nucleosides, Nucleotides, Nucleic Acids, 21, 849-861.
    • (2002) Nucleosides, Nucleotides, Nucleic Acids , vol.21 , pp. 849-861
    • Takamatsu, S.1    Katayama, S.2    Hirose, N.3
  • 81
    • 0023914007 scopus 로고
    • Potent and selective activity of 3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside, 3'-fluoro-2,6-diaminopurine-2',3'-dideoxyriboside, and 3' -fluoro-2',3'-dideoxyguanosine against human immunodeficiency virus
    • Balzarini, J., Baba, M., Pauwels, R., et al. (1988) Potent and selective activity of 3'-azido-2,6-diaminopurine-2',3'-dideoxyriboside, 3'-fluoro-2,6-diaminopurine-2',3'-dideoxyriboside, and 3' -fluoro-2',3'-dideoxyguanosine against human immunodeficiency virus. Mol. Pharmacol., 33, 243-249.
    • (1988) Mol. Pharmacol. , vol.33 , pp. 243-249
    • Balzarini, J.1    Baba, M.2    Pauwels, R.3
  • 82
    • 0023713363 scopus 로고
    • Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides
    • Herdewijn, P., Balzarini, J., Baba, M., et al. (1988) Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides. J. Med. Chem., 31, 2040-2048.
    • (1988) J. Med. Chem. , vol.31 , pp. 2040-2048
    • Herdewijn, P.1    Balzarini, J.2    Baba, M.3
  • 83
    • 0031964879 scopus 로고    scopus 로고
    • Inhibition of human and duck hepatitis B virus by 2',3'-dideoxy-3'-fluoroguanosine in vitro
    • Schröder, I., Holmgren, B., Öberg, M. and Löfgren, B. (1998) Inhibition of human and duck hepatitis B virus by 2',3'-dideoxy-3'-fluoroguanosine in vitro. Antivir. Res., 37, 57-66.
    • (1998) Antivir. Res. , vol.37 , pp. 57-66
    • Schröder, I.1    Holmgren, B.2    Öberg, M.3    Löfgren, B.4
  • 84
    • 0029915195 scopus 로고    scopus 로고
    • Inhibition of duck hepatitis B virus replication by 2',3'-dideoxy-3'-fluoro- guanosine in vitro and in vivo
    • Hafkemeyer, P., Keppler-Hafkemeyer, A., al Haya, M. A., et al. (1996) Inhibition of duck hepatitis B virus replication by 2',3'-dideoxy-3'-fluoro- guanosine in vitro and in vivo. Antimi-crob. Agents Chemother. 40, 792-794.
    • (1996) Antimi-crob. Agents Chemother. , vol.40 , pp. 792-794
    • Hafkemeyer, P.1    Keppler-Hafkemeyer, A.2    Al Haya, M.A.3
  • 85
    • 33644642052 scopus 로고    scopus 로고
    • In vitro characterization of the anti-hepatitis B virus activity and cross-resistance profile of 2',3'-dideoxy-3'-fluoroguanosine
    • Jacquard, A.-C., Brunelle, M.-N., Pichoud, C., et al. (2006) In vitro characterization of the anti-hepatitis B virus activity and cross-resistance profile of 2',3'-dideoxy-3'-fluoroguanosine. Antimicrob. Agents Chemother., 50, 955-961.
    • (2006) Antimicrob. Agents Chemother. , vol.50 , pp. 955-961
    • Jacquard, A.-C.1    Brunelle, M.-N.2    Pichoud, C.3
  • 86
    • 0034018134 scopus 로고    scopus 로고
    • Synthesis and antiviral evaluation of unnatural ß-L-enantiomers of 3'-fluoro- and 3'-azido-2',3'-dideoxy- guanosine derivatives
    • Marchand, A. Mathé, C., Imbach, J.-L. and Gosselin, G. (2000) Synthesis and antiviral evaluation of unnatural ß-L-enantiomers of 3'-fluoro- and 3'-azido-2',3'-dideoxy- guanosine derivatives. Nucleosides, Nucleotides Nucleic Acids, 19, 205-217.
    • (2000) Nucleosides, Nucleotides Nucleic Acids , vol.19 , pp. 205-217
    • Marchand, A.1    Mathé, C.2    Imbach, J.-L.3    Gosselin, G.4
  • 87
    • 0034675036 scopus 로고    scopus 로고
    • Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol
    • Chun, B. K., Schinazi, R. F., Cheng, Y. C. and Chu, C. K. (2000) Synthesis of 2',3'-dideoxy-3'-fluoro-L-ribonucleosides as potential antiviral agents from D-sorbitol. Carbohydr. Res., 328, 49-59.
    • (2000) Carbohydr. Res. , vol.328 , pp. 49-59
    • Chun, B.K.1    Schinazi, R.F.2    Cheng, Y.C.3    Chu, C.K.4
  • 88
    • 0034840089 scopus 로고    scopus 로고
    • Large-scale manufacturing of all four 2 -deoxynucleosides via novel strategies including a chemo- enzymatic process
    • Komatsu, H., Awano, H., Tanikawa, H., et al. (2001) Large-scale manufacturing of all four 2 -deoxynucleosides via novel strategies including a chemo- enzymatic process. Nucleosides, Nucleotides Nucleic Acids, 20, 1291-1293.
    • (2001) Nucleosides, Nucleotides Nucleic Acids , vol.20 , pp. 1291-1293
    • Komatsu, H.1    Awano, H.2    Tanikawa, H.3
  • 89
    • 0037474658 scopus 로고    scopus 로고
    • Chemo-enzymatic synthesis of 2',3'-dideoxy-3'- fluoro-ß-D-guanosine via 2,3-dideoxy-3-fluoro-a-D-ribose 1-phosphate
    • Komatsu, H. and Araki, T. (2003) Chemo-enzymatic synthesis of 2',3'-dideoxy-3'- fluoro-ß-D-guanosine via 2,3-dideoxy-3-fluoro-a-D-ribose 1-phosphate. Tetrahedron Lett., 44, 2899-2901.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2899-2901
    • Komatsu, H.1    Araki, T.2
  • 90
    • 33746307895 scopus 로고    scopus 로고
    • Synthesis of 6-arylthio analogs of 2',3'-dideoxy-3'-fluoroguanosine and their effect against hepatitis B virus replication
    • Torii, T., Onishi, T., Izawa, K., et al. (2006) Synthesis of 6-arylthio analogs of 2',3'-dideoxy-3'-fluoroguanosine and their effect against hepatitis B virus replication. Nucleosides, Nucleo-tides Nucleic Acids, 25, 655-665.
    • (2006) Nucleosides, Nucleo-tides Nucleic Acids , vol.25 , pp. 655-665
    • Torii, T.1    Onishi, T.2    Izawa, K.3
  • 92
    • 84889351591 scopus 로고    scopus 로고
    • Regioselective preparation of 2-halo-2,3-dideoxy-3-fluoro-ß-D-arabinofuranosyl nucleosides and their dehalogenation products
    • JP Patent 2006022009
    • Ishii, A., Otsuka, T., Kume, K., et al. (2006) Regioselective preparation of 2-halo-2,3-dideoxy-3-fluoro-ß-D-arabinofuranosyl nucleosides and their dehalogenation products. JP Patent 2006022009.
    • (2006)
    • Ishii, A.1    Otsuka, T.2    Kume, K.3
  • 93
    • 33746294078 scopus 로고    scopus 로고
    • A concise synthesis of 3'-a-fluoro-2',3'-dideoxyguanosine (FddG) via 3'-a-selective fluorination of 8,2'-thioanhydronucleoside
    • Torii, T., Onishi, T., Izawa, K. and Maruyama, T. (2006) A concise synthesis of 3'-a-fluoro-2',3'-dideoxyguanosine (FddG) via 3'-a-selective fluorination of 8,2'-thioanhydronucleoside. Tetrahedron Lett., 47, 6139-6141.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 6139-6141
    • Torii, T.1    Onishi, T.2    Izawa, K.3    Maruyama, T.4
  • 94
    • 0542405231 scopus 로고
    • Nucleosides. XLIX. Nuclear magnetic resonance studies of 2' -and 3'-halogeno nucleosides. The conformations of 2'-deoxy-2'-fluorouridine and 3'-deoxy-3'-fluoro-ß-D-arabinofuranosyluracil
    • Cushley, R. J., Codington, J. F. and Fox, J. J. (1968) Nucleosides. XLIX. Nuclear magnetic resonance studies of 2' -and 3'-halogeno nucleosides. The conformations of 2'-deoxy-2'-fluorouridine and 3'-deoxy-3'-fluoro-ß-D-arabinofuranosyluracil. Can. J. Chem., 46, 1131-1140.
    • (1968) Can. J. Chem. , vol.46 , pp. 1131-1140
    • Cushley, R.J.1    Codington, J.F.2    Fox, J.J.3
  • 95
    • 0019332380 scopus 로고
    • Nucleoside conformation is determined by the electronegativity of the sugar substituent
    • Guschlbauer, W. and Krzysztof, J. (1980) Nucleoside conformation is determined by the electronegativity of the sugar substituent. Nucleic Acids Res., 8, 1421-1433.
    • (1980) Nucleic Acids Res. , vol.8 , pp. 1421-1433
    • Guschlbauer, W.1    Krzysztof, J.2
  • 96
    • 0019877868 scopus 로고
    • The crystal and molecular structure of 2' -deoxy-2'-fluoroinosine monohydrate
    • Hakoshima, T., Omori, H., Tomita, K., et al. (1981) The crystal and molecular structure of 2' -deoxy-2'-fluoroinosine monohydrate. Nucleic Acids Res., 9, 711-729.
    • (1981) Nucleic Acids Res. , vol.9 , pp. 711-729
    • Hakoshima, T.1    Omori, H.2    Tomita, K.3
  • 97
    • 0019852024 scopus 로고
    • Studies on nucleosides and nucleotides. LXXXVIII. Purine cyclo-nucleosides. XLIII. 13C NMR spectra of 2'-substituted 2'-deoxyadenosines. Substituent effects on the chemical shifts in the furanose ring system
    • Uesugi, S., Miki, H. and Ikehara, M. (1981) Studies on nucleosides and nucleotides. LXXXVIII. Purine cyclo-nucleosides. XLIII. 13C NMR spectra of 2'-substituted 2'-deoxyadenosines. Substituent effects on the chemical shifts in the furanose ring system. Chem. Pharm. Bull., 29, 2199-2204.
    • (1981) Chem. Pharm. Bull. , vol.29 , pp. 2199-2204
    • Uesugi, S.1    Miki, H.2    Ikehara, M.3
  • 98
    • 0019889025 scopus 로고
    • Synthesis and characterization of the dinucleoside monophosphates containing 2'-fluoro-2'-deoxyadenosine
    • Uesugi, S., Takatsuka, Y., Ikehara, M., et al. (1981) Synthesis and characterization of the dinucleoside monophosphates containing 2'-fluoro-2'-deoxyadenosine. Biochemistry, 20, 3056-3062.
    • (1981) Biochemistry , vol.20 , pp. 3056-3062
    • Uesugi, S.1    Takatsuka, Y.2    Ikehara, M.3
  • 99
    • 0019832060 scopus 로고
    • A study of antitemplate inhibition of mammalian, bacterial and viral DNA polymerases by 2- and 2' -substituted derivatives of polyade-nylic acid
    • Chandra, P., Demirhan, I. and De Clercq, E. (1981) A study of antitemplate inhibition of mammalian, bacterial and viral DNA polymerases by 2- and 2' -substituted derivatives of polyade-nylic acid. Cancer Lett., 12, 181-193.
    • (1981) Cancer Lett. , vol.12 , pp. 181-193
    • Chandra, P.1    Demirhan, I.2    De Clercq, E.3
  • 100
    • 0020317476 scopus 로고
    • Template activity of poly(2'-fluoro-2'-deoxyinosinic acid) for murine leukemia virus reverse transcriptase
    • Fukui, T., De Clerq, E., Kakiuchi, N. and Ikehara, M. (1982) Template activity of poly(2'-fluoro-2'-deoxyinosinic acid) for murine leukemia virus reverse transcriptase. Cancer Lett.,16, 129-135.
    • (1982) Cancer Lett. , vol.16 , pp. 129-135
    • Fukui, T.1    De Clerq, E.2    Kakiuchi, N.3    Ikehara, M.4
  • 101
    • 0021946206 scopus 로고
    • 2'-Fluoro-2'-deoxypolynucleotides as templates and inhibitors for RNA- and DNA-dependent DNA poly-merases
    • Aoyama, H., Sarih-Cottin, L., Tarrago-Litvak, L., et al. (1985) 2'-Fluoro-2'-deoxypolynucleotides as templates and inhibitors for RNA- and DNA-dependent DNA poly-merases. Biochim. Biophys. Acta, 824, 225-232.
    • (1985) Biochim. Biophys. Acta , vol.824 , pp. 225-232
    • Aoyama, H.1    Sarih-Cottin, L.2    Tarrago-Litvak, L.3
  • 102
    • 0020494453 scopus 로고
    • Protein synthesis using poly(2'-halogeno-2'-deoxyadenylic acids) as messenger
    • Fukui, T., Kakiuchi, N. and Ikehara, M. (1982) Protein synthesis using poly(2'-halogeno-2'-deoxyadenylic acids) as messenger. Biochim. Biophys. Acta, 697, 174-177.
    • (1982) Biochim. Biophys. Acta , vol.697 , pp. 174-177
    • Fukui, T.1    Kakiuchi, N.2    Ikehara, M.3
  • 103
    • 0028606974 scopus 로고
    • Translation of 2'-modified mRNA in vitro and in vivo
    • Aurup, H., Siebert, A., Benseler, F., et al. (1994) Translation of 2'-modified mRNA in vitro and in vivo. Nucleic Acids Res., 22, 4963-4968.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 4963-4968
    • Aurup, H.1    Siebert, A.2    Benseler, F.3
  • 104
    • 0019313820 scopus 로고
    • Interferon induction by two 2'-modified double-helical RNAs, poly(2'-nuoro-2'-deoxymosimc acid) • poly(cytidylic acid) and poly(2'-chloro-2'-deoxyinosinic acid) • poly(cytidylic acid)
    • De Clercq, E., Stollar, B. D., Hobbs, J., et al. (1980) Interferon induction by two 2'-modified double-helical RNAs, poly(2'-nuoro-2'-deoxymosimc acid) • poly(cytidylic acid) and poly(2'-chloro-2'-deoxyinosinic acid) • poly(cytidylic acid). Eur. J. Biochem., 107, 279-288.
    • (1980) Eur. J. Biochem. , vol.107 , pp. 279-288
    • De Clercq, E.1    Stollar, B.D.2    Hobbs, J.3
  • 105
    • 0027400040 scopus 로고
    • Purine 2'-deoxy-2'-fluororibosides as antiinfluenza virus agents
    • Tuttle, J. V., Tisdale, M. and Krenitsky, T. A. (1993) Purine 2'-deoxy-2'-fluororibosides as antiinfluenza virus agents. J. Med. Chem., 36, 119-125.
    • (1993) J. Med. Chem. , vol.36 , pp. 119-125
    • Tuttle, J.V.1    Tisdale, M.2    Krenitsky, T.A.3
  • 106
    • 0027423178 scopus 로고
    • Inhibition of influenza A and B viruses by 2'-deoxy-2'-fluororibosides
    • Tisdale, M., Appleyard, G., Tuttle, et al. (1993) Inhibition of influenza A and B viruses by 2'-deoxy-2'-fluororibosides. Antiviral Chem. Chemother., 4, 281-287.
    • (1993) Antiviral Chem. Chemother. , vol.4 , pp. 281-287
    • Tisdale, M.1    Appleyard, G.2    Tuttle3
  • 107
    • 23944469297 scopus 로고    scopus 로고
    • Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication
    • Clark, J. L., Hollecker, L., Mason, J. C., et al. (2005) Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication. J. Med. Chem., 48, 5504-5508.
    • (2005) J. Med. Chem. , vol.48 , pp. 5504-5508
    • Clark, J.L.1    Hollecker, L.2    Mason, J.C.3
  • 108
    • 33846589710 scopus 로고    scopus 로고
    • Mechanism of activation of ß-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase
    • Murakami, E., Bao, H., Ramesh, M., et al. (2007) Mechanism of activation of ß-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase. Antimicrob. Agents Chemother. 51, 503-509.
    • (2007) Antimicrob. Agents Chemother. , vol.51 , pp. 503-509
    • Murakami, E.1    Bao, H.2    Ramesh, M.3
  • 109
    • 0034687083 scopus 로고    scopus 로고
    • Interactions of conformationally biased north and south 2'-fluoro-2',3'-dideoxynucleoside 5'-triphosphates with the active site of HIV-1 reverse transcriptase
    • Mu, L., Sarafianos, S. G., Nicklaus, M. C., et al. (2000) Interactions of conformationally biased north and south 2'-fluoro-2',3'-dideoxynucleoside 5'-triphosphates with the active site of HIV-1 reverse transcriptase. Biochemistry, 39, 11205-11215.
    • (2000) Biochemistry , vol.39 , pp. 11205-11215
    • Mu, L.1    Sarafianos, S.G.2    Nicklaus, M.C.3
  • 110
    • 84889306963 scopus 로고
    • Conformational characteristics of 3'-deoxy-3'-fluoro- and 2',3'-dideoxy-3'-fluororibonucleosides
    • Khripach, N. B., Pupeiko, N. E., Skorynin, I. Yu. and Borisov, E. V. (1991) Conformational characteristics of 3'-deoxy-3'-fluoro- and 2',3'-dideoxy-3'-fluororibonucleosides. Bioor-ganicheskaya Khimiya, 17, 1521-1525.
    • (1991) Bioor-ganicheskaya Khimiya , vol.17 , pp. 1521-1525
    • Khripach, N.B.1    Pupeiko, N.E.2    Skorynin, I.Y.3    Borisov, E.V.4
  • 111
    • 0025910389 scopus 로고
    • Structural studies of anti-HIV 3'-a-fluorothymidine and 3'-a-azidothymidine by 500 MHz 1H-NMR spectroscopy and molecular mechanics (MM2) calculations
    • Plavec, J., Koole, L. H., Sandström, A. and Chattopadhyaya, J. (1991) Structural studies of anti-HIV 3'-a-fluorothymidine and 3'-a-azidothymidine by 500 MHz 1H-NMR spectroscopy and molecular mechanics (MM2) calculations. Tetrahedron, 47, 7363-7376.
    • (1991) Tetrahedron , vol.47 , pp. 7363-7376
    • Plavec, J.1    Koole, L.H.2    Sandström, A.3    Chattopadhyaya, J.4
  • 112
    • 0031055109 scopus 로고    scopus 로고
    • Conformational analysis of the complete series of 2' and 3' monofluorinated dideoxyuridines
    • Barchi, J. J., Jr, Jeong, L.-S., Siddiqui, M. A. and Marquez, V. E. (1997) Conformational analysis of the complete series of 2' and 3' monofluorinated dideoxyuridines. J. Biochem. Biophys. Methods, 34, 11-29.
    • (1997) J. Biochem. Biophys. Methods , vol.34 , pp. 11-29
    • Barchi Jr., J.J.1    Jeong, L.-S.2    Siddiqui, M.A.3    Marquez, V.E.4
  • 113
    • 0000137138 scopus 로고
    • Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus
    • Van Roey, P., Salerno, J. M., Chu, C. K. and Schinazi, R. F. (1989) Correlation between preferred sugar ring conformation and activity of nucleoside analogues against human immunodeficiency virus. Proc. Natl. Acad. Sci. USA, 86, 3929-3933.
    • (1989) Proc. Natl. Acad. Sci. USA , vol.86 , pp. 3929-3933
    • Van Roey, P.1    Salerno, J.M.2    Chu, C.K.3    Schinazi, R.F.4


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