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Volumn 28, Issue 5-7, 2009, Pages 519-536

Synthesis and antiviral activity of purine 2',3'-dideoxy-2',3'-difluoro-D- arabinofuranosyl nucleosides

Author keywords

Antiviral activity; Conformational analysis; Fluoro nucleosides; Purines

Indexed keywords

2 CHLORO 9 (2',3' DIDEOXY 2,3 DIFLUORO BETA DEXTRO ARABINOFURANOSYL)ADENINE; 9 (2',3' DIDEOXY 2',3' DIFLUORO BETA DEXTRO ARABINOFURANOSYL)ADENINE; ADENINE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PURINE 2',3' DIDEOXY 2',3' DIFLUORO DEXTRO ARABINOFURANOSYL NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 75749124237     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770903053979     Document Type: Article
Times cited : (8)

References (30)
  • 1
    • 0043239160 scopus 로고    scopus 로고
    • Probing the mechanistic consequences of 5-fluorine substitution on cytidine nucleotide analogue incorporation by HIV-1 reverse transcriptase
    • Ray, A.S.; Schinazi, R.F.; Murakami, E.; Basavapathruni, A.; Shi, J.; et al. Probing the mechanistic consequences of 5-fluorine substitution on cytidine nucleotide analogue incorporation by HIV-1 reverse transcriptase. Antiv. Chem. Chemother. 2003, 14, 115-125.
    • (2003) Antiv. Chem. Chemother. , vol.14 , pp. 115-125
    • Ray, A.S.1    Schinazi, R.F.2    Murakami, E.3    Basavapathruni, A.4    Shi, J.5
  • 2
    • 0037075785 scopus 로고    scopus 로고
    • Structure-Activity Relationships of 2-fluoro-2,3-unsaturated d-nucleosides as anti-HIV-1 agents
    • Lee, K.; Choi, Y.; Gumina, G.; Zhou, W.; Schinazi, R.F.; Chu, C.K. Structure-Activity Relationships of 2-fluoro-2,3-unsaturated d-nucleosides as anti-HIV-1 agents. J. Med. Chem. 2002, 45, 1313-1320.
    • (2002) J. Med. Chem. , vol.45 , pp. 1313-1320
    • Lee, K.1    Choi, Y.2    Gumina, G.3    Zhou, W.4    Schinazi, R.F.5    Chu, C.K.6
  • 3
    • 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
    • Clarck, J.L.; Hollecker, L.; Mason, J.C.; Stuyver, L.J.; Tharnish, P.M.; et al. Design, synthesis, and antiviral activity of 2-deoxy-2-fluoro-2-C- methylcytidine, a potent inhibitor of hepatitis C virus replication. J. Med. Chem. 2005, 48, 5504-5508.
    • (2005) J. Med. Chem. , vol.48 , pp. 5504-5508
    • Clarck, J.L.1    Hollecker, L.2    Mason, J.C.3    Stuyver, L.J.4    Tharnish, P.M.5
  • 4
    • 13444261067 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of a series of D- and L-2-deoxy-2-fluororibonucleosides in the subgenomic HCV replicon system
    • Shi, J.; Du, J.; Ma, T.; Pankiewicz, K.W.; Patterson, S.E.; et al. Synthesis and antiviral 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    Pankiewicz, K.W.4    Patterson, S.E.5
  • 5
    • 0025360397 scopus 로고
    • Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1)
    • Martin, J.A.; Busnell, D.J.; Duncan, I.B.; Dunsdon, S.J.; Hall, M.J.; et al. Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1). J. Med. Chem. 1990, 33, 2137-2145.
    • (1990) J. Med. Chem. , vol.33 , pp. 2137-2145
    • Martin, J.A.1    Busnell, D.J.2    Duncan, I.B.3    Dunsdon, S.J.4    Hall, M.J.5
  • 6
    • 0023551961 scopus 로고
    • Synthesis and anti-HIV activity of various 2- and3-substituted 2,3-dideoxyadenosines: A structure-activity analysis
    • Herdewijn, P.; Pauwels, R.; Baba, M.; Balzarini, J.; De Clercq, E. Synthesis and anti-HIV activity of various 2- and3-substituted 2,3-dideoxyadenosines: A structure-activity analysis. J. Med. Chem. 1987, 30, 2131-2137.
    • (1987) J. Med. Chem. , vol.30 , pp. 2131-2137
    • Herdewijn, P.1    Pauwels, R.2    Baba, M.3    Balzarini, J.4    De Clercq, E.5
  • 7
    • 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.; Kelly, J.A.; Mitsuya, H.; Broder, S.; et al. 2,3-Dideoxy-2-fluoro-ara- A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV). Biochem. Pharmacol. 1987, 36, 2719-2722.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2719-2722
    • Marquez, V.E.1    Tseng, C.K.-H.2    Kelly, J.A.3    Mitsuya, H.4    Broder, S.5
  • 10
    • 0028886685 scopus 로고
    • Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides
    • Mikhailopulo, I.A.; Sivets, G.G.; Poopeiko, N.E.; Khripach, N.B. Oxidation-reduction sequence for the synthesis of peracylated fluorodeoxy pentofuranosides. Carbohyd. Res. 1995, 278, 71-89.
    • (1995) Carbohyd. Res. , vol.278 , pp. 71-89
    • Mikhailopulo, I.A.1    Sivets, G.G.2    Poopeiko, N.E.3    Khripach, N.B.4
  • 11
    • 10644276204 scopus 로고
    • Design and reactivity of organic functional groups: Imidazolylsulfonate (imidazylate)-an efficient and versatile leaving group
    • Hanessian, S.; Vatele, J.-M. Design and reactivity of organic functional groups: imidazolylsulfonate (imidazylate)-an efficient and versatile leaving group. Tetrahedron Lett. 1981, 22, 3579-3582.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 3579-3582
    • Hanessian, S.1    Vatele, J.-M.2
  • 12
    • 0019994479 scopus 로고
    • Improved synthesis of -d-ribofuranosides via stereoselective alkylation of a dibutylstannylene derivative for ready access to the 2-substituted 2-deoxyarabinofuranosides
    • Su, T.-L.; Klein, R.S.; Fox, J.J. Improved synthesis of -d-ribofuranosides via stereoselective alkylation of a dibutylstannylene derivative for ready access to the 2-substituted 2-deoxyarabinofuranosides. J. Org. Chem. 1981, 47, 1506-1509.
    • (1981) J. Org. Chem. , vol.47 , pp. 1506-1509
    • Su, T.-L.1    Klein, R.S.2    Fox, J.J.3
  • 13
    • 34948867673 scopus 로고    scopus 로고
    • Synthesis and conformational analysis of 1- and 3-substituted 2-deoxy-2-fluoro-d-ribofuranosyl nucleosides
    • Sivets, G.G.; Kalinichenko, E.N.; Mikhailopulo, I.A. Synthesis and conformational analysis of 1- and 3-substituted 2-deoxy-2-fluoro-d-ribofuranosyl nucleosides. Helv. Chim. Acta. 2007, 90, 1818-1836.
    • (2007) Helv. Chim. Acta. , vol.90 , pp. 1818-1836
    • Sivets, G.G.1    Kalinichenko, E.N.2    Mikhailopulo, I.A.3
  • 14
    • 0022341203 scopus 로고
    • An efficient synthesis of 1-(2-deoxy-2-fluoro-d-arabinofuranosyl)-5- iodouracil (FIAU) and 1-(2-deoxy-2-fluoro-darabinofuranosyl) thymine (FMAU)
    • Tann, C.H.; Brodfuehrer, P.R.; Brundidge, S.P.; Sapino, C. Jr.; Howell, H.G. An efficient synthesis of 1-(2-deoxy-2-fluoro-d-arabinofuranosyl)-5- iodouracil (FIAU) and 1-(2-deoxy-2-fluoro-darabinofuranosyl) thymine (FMAU). J. Org. Chem. 1985, 50, 3644-3647.
    • (1985) J. Org. Chem. , vol.50 , pp. 3644-3647
    • Tann, C.H.1    Brodfuehrer, P.R.2    Brundidge, S.P.3    Sapino Jr., C.4    Howell, H.G.5
  • 15
    • 0032719259 scopus 로고    scopus 로고
    • A Novel route for the synthesis of deoxy fluoro sugars and nucleosides
    • Mikahilopulo, I.A.; Sivets, G.G. A Novel route for the synthesis of deoxy fluoro sugars and nucleosides. Helv. Chim. Acta. 1999, 82, 2052-2065.
    • (1999) Helv. Chim. Acta. , vol.82 , pp. 2052-2065
    • Mikahilopulo, I.A.1    Sivets, G.G.2
  • 16
    • 0001263799 scopus 로고
    • Trimethylsilyl bromide as amild, stereoselective anomeric brominating agent
    • Gillard, J.W.; Israel, M. Trimethylsilyl bromide as amild, stereoselective anomeric brominating agent. Tetrahedron Lett. 1981, 22, 513-516.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 513-516
    • Gillard, J.W.1    Israel, M.2
  • 17
    • 33845470620 scopus 로고
    • Synthesis of 2-Deoxytubercidin, 2-deoxyadenosine, and related 2-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure
    • Kazimierczuk, Z.; Cottam, H.B.; Revankar, G.R.; Robins, R.K. Synthesis of 2-Deoxytubercidin, 2-deoxyadenosine, and related 2-deoxynucleosides via a novel direct stereospecific sodium salt glycosylation procedure. J. Am. Chem. Soc. 1984, 106, 6379-6382.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 6379-6382
    • Kazimierczuk, Z.1    Cottam, H.B.2    Revankar, G.R.3    Robins, R.K.4
  • 18
  • 19
    • 0025879048 scopus 로고
    • Synthesis and antiviral and cytostatic properties of 3-deoxy-3-fluoro- and 2-azido-3-fluoro-2,3 - Dideoxy-d-ribofuranisides of natural heterocyclic bases
    • Mikhailopulo, I.A.; Poopeiko, N.E.; Pricota, T.I.; Sivets, G.G.; Kvasyuk, E.I.; Balzarini, J.; De Clercq, E. Synthesis and antiviral and cytostatic properties of 3-deoxy-3-fluoro- and 2-azido-3-fluoro-2,3 - dideoxy-d- ribofuranisides of natural heterocyclic bases. J. Med. Chem. 1991, 34, 2195-2202.
    • (1991) J. Med. Chem. , vol.34 , pp. 2195-2202
    • Mikhailopulo, I.A.1    Poopeiko, N.E.2    Pricota, T.I.3    Sivets, G.G.4    Kvasyuk, E.I.5    Balzarini, J.6    De Clercq, E.7
  • 21
    • 0034631782 scopus 로고    scopus 로고
    • NMR spectra of fluorinated carbohydrates
    • Michalik, M.; Hein, M.; Frank, M. NMR spectra of fluorinated carbohydrates. Carbohyd. Res. 2000, 327, 185-218.
    • (2000) Carbohyd. Res. , vol.327 , pp. 185-218
    • Michalik, M.1    Hein, M.2    Frank, M.3
  • 22
    • 33746137726 scopus 로고    scopus 로고
    • Synthesis of C2-fluoro-substituted adenine nucleosides via pivaloyl derivatives of adenosine and 3-deoxyadenosine
    • Sivets, G.G.; Kalinichenko, E.N.; Mikahilopulo, I.A. Synthesis of C2-fluoro-substituted adenine nucleosides via pivaloyl derivatives of adenosine and 3-deoxyadenosine. Lett. Org. Chem. 2006, 3, 402-408.
    • (2006) Lett. Org. Chem. , vol.3 , pp. 402-408
    • Sivets, G.G.1    Kalinichenko, E.N.2    Mikahilopulo, I.A.3
  • 23
    • 0026523623 scopus 로고
    • HIV inhibitors targeted at the reverse transcriptases
    • De Clercq, E. HIV inhibitors targeted at the reverse transcriptases. AIDS Res. Human Retroviruses 1992, 8, 119-134.
    • (1992) AIDS Res. Human Retroviruses , vol.8 , pp. 119-134
    • De Clercq, E.1
  • 24
    • 0025362229 scopus 로고
    • Activities of 3-azido-3- Deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1
    • Schinazi, R.F.; Sommadossi, J.P.; Saalmann, V.; Cannon, D.L.; Xie, M.-W.; et al. Activities of 3-azido-3- deoxythymidine nucleotide dimers in primary lymphocytes infected with human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 1990, 34, 1061-1067.
    • (1990) Antimicrob. Agents Chemother. , vol.34 , pp. 1061-1067
    • Schinazi, R.F.1    Sommadossi, J.P.2    Saalmann, V.3    Cannon, D.L.4    Xie, M.-W.5
  • 25
    • 0036894245 scopus 로고    scopus 로고
    • Antiviral activities and cellular toxicities of modified 2,3-dideoxy-2,3-didehydrocytidine analogues
    • Stuyver, L.J.; Lostia, S.; Adams, M.; Mathew, J.; Pai, B.S.; et al. Antiviral activities and cellular toxicities of modified 2,3-dideoxy-2,3- didehydrocytidine analogues. Antimicrob. Agents Chemother. 2002, 46, 3854-3860.
    • (2002) Antimicrob. Agents Chemother. , vol.46 , pp. 3854-3860
    • Stuyver, L.J.1    Lostia, S.2    Adams, M.3    Mathew, J.4    Pai, B.S.5
  • 27
    • 0038711356 scopus 로고    scopus 로고
    • 2-Chloro-2,3-dideoxy-3-fluoro-dribofuranosides: Synthesis, stereospecificity, some chemical transformations, and conformational analysis
    • Mikahilopulo, I.A.; Pricota, T.I.; Sivets, G.G.; Altona, C. 2-Chloro-2,3-dideoxy-3-fluoro-dribofuranosides: synthesis, stereospecificity, some chemical transformations, and conformational analysis. J. Org. Chem. 2003, 68, 5897-5908.
    • (2003) J. Org. Chem. , vol.68 , pp. 5897-5908
    • Mikahilopulo, I.A.1    Pricota, T.I.2    Sivets, G.G.3    Altona, C.4
  • 28
    • 0001131448 scopus 로고    scopus 로고
    • A new generalized Karplus-type equation relating vicinal proton-fluorine coupling constants to H-C-C-F torsion angles
    • Thibaudeau, C.; Plavec, J.; Chattopadhyaya, J. A new generalized Karplus-type equation relating vicinal proton-fluorine coupling constants to H-C-C-F torsion angles. J. Org. Chem. 1998, 63, 4967-4984.
    • (1998) J. Org. Chem. , vol.63 , pp. 4967-4984
    • Thibaudeau, C.1    Plavec, J.2    Chattopadhyaya, J.3
  • 29
    • 0040609327 scopus 로고    scopus 로고
    • Adenosine deaminase prefers a distinct sugar ring conformation for binding and catalysis: Kinetic and structural studies
    • Ford, H.; Dai, F.;Mu, L.; Siddiqui, M.A.; Nicklaus, M.C.; et al. Adenosine deaminase prefers a distinct sugar ring conformation for binding and catalysis: kinetic and structural studies. Biochemistry 2000, 39, 2581-2592.
    • (2000) Biochemistry , vol.39 , pp. 2581-2592
    • Ford, H.1    Dai, F.2    Mu, L.3    Siddiqui, M.A.4    Nicklaus, M.C.5
  • 30
    • 47349092659 scopus 로고    scopus 로고
    • Comprehensive structural studies of 2,3-difluorinated nucleosides: Comparison of theory, solution and solid state
    • Barchi, J.J.; Karki, R.G.; Nicklaus, M.C.; Siddiqui, M.A.; Clifford, G.; et al. Comprehensive structural studies of 2,3-difluorinated nucleosides: comparison of theory, solution and solid state. J. Am. Chem. Soc. 2008, 130, 8048-8057.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 8048-8057
    • Barchi, J.J.1    Karki, R.G.2    Nicklaus, M.C.3    Siddiqui, M.A.4    Clifford, G.5


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