Synthesis and Cytotoxic Activity of Novel 5-Substituted-1-(β-L-Arabinofuranosyl) Pyrimidine Nucleosides

REFERENCES

• Smejkal , J. and Sorm , F. 1964 . Nucleic acid components and their analogues. 53. Preparation of 1-(2-deoxy-ß-L-ribofuranosyl)thymine (L-thymidine) . Collect. Czech. Chem. Commun. , 29 : 2809 – 2813 .
   Web of Science ®Google Scholar
• Schinazi , R. F. , Chu , C. K. , Peck , A. , McMillan , A. , Mathis , S. , Cannon , D. , Jeong , L. S. , Beach , J. W. , Choi , W. B. , Yeola , S. and Liotta , D. C. 1992 . Activities of the four optical isomers of 2′,3′-dideoxy-3′-thiacytidine (BCH-189) against human immunideficiency virus type I in human lymphocytes . Antimicrob. Agents Chemother. , 36 : 672 – 676 .
   PubMed Web of Science ®Google Scholar
• Schinazi , R. F. , McMillan , A. , Cannon , D. , Mathis , R. , Lloyd , R. M. , Peck , A. , Sommadossi , J.-P. , St.Clair , M. , Wilson , J. , Furman , P. A. , Painter , G. , Choi , W. B. and Liotta , D. C. 1992 . Selective inhibition of human immunodeficiency viruses by racemates and enentiomers of cis-5-fluoro-1-[2-(hydroxymethyl-1,3-oxathiolan-5-yl]cytosine . Antimicrob. Agents Chemother. , 36 : 2423 – 2431 .
   PubMed Web of Science ®Google Scholar
• Grant , R. M. , Lama , J. R. , Anderson , P. L. , McMahan , V. , Liu , A. Y. , Vargas , L. , Goicochea , P. , Casapia , M. , Guanira-Carranza , J. V. , Ramirez-Cardich , M. E. , Montoya-Herrera , O. , Fernandez , T. , Veloso , V. G. , Buchbinder , S. P. , Chariyalertsak , S. , Schechter , M. , Bekker , L. G. , Mayer , K. H. , Kallas , E. G. , Amico , K. R. , Mulligan , K. , Bushman , L. R. , Hance , R. J. , Ganoza , C. , Defechereux , P. , Postle , B. , Wang , F. , McConnell , J. , Zheng , J. H. , Lee , J. , Rooney , J. F. , Jaffe , H. S. , Martinez , A. I. , Burns , D. N. and Glidden , D. V. 2010 . Preexposure chemoprophylaxis for HIV prevention in men who have sex with men . New Engl. J. Med. , 363 : 2587 – 2599 .
   PubMed Web of Science ®Google Scholar
• Gosselin , G. , Pierra , C. , Benzaria , S. , Dukhan , D. , Imbach , J.-L. , Loi , A. G. , LaColla , P. , Cretton-Scott , E. , Bridges , E. G. , Standring , D. and Sommadossi , J.-P. 2004 . “ ß-L-2′-deoxythymidine (LdT) and ß-L-2′-deoxycytidine (LdC): how simole structures can be potent, selective and specific anti-HBV drugs ” . In Frontiers in Nucleosides and Nucleic Acids , Edited by: Schinazi , R. F. and Liotta , D. C. 309 – 317 . Tucker , Georgia : IHL Press .
   Google Scholar
• Biron , K. K. , Harvey , R. J. , Chamberlain , S. C. , Good , S. S. , Smith , A. A. III , Davis , M. G. , Talarico , C. L. , Miller , W. H. , Ferris , R. , Dornsife , R. E. , Stanat , S. C. , Townsend , L. B. and Kozalska , G. W. 2002 . Potent and selective inhibition of human cytomegalovirus replication by 1263W94: a benzimidazole L-riboside with a unique mode of action . Antimicrob. Agents Chemother. , 46 : 2365 – 2372 .
   PubMed Web of Science ®Google Scholar
• Walker , M. P. , Appleby , T. C. , Zhong , W. , Lau , J. Y.N. and Hong , Z. 2003 . Hepatitis C virus therapies: current treatments, targets and future perspectives . Antiviral Chem. Chemother. , 14 : 1 – 21 .
   Google Scholar
• Kim , H. O. , Schinazi , R. F. , Shanmuganathan , K. , Jeong , L. S. , Beach , J. W. , Nampalli , S. , Cannon , D. L. and Chu , C. K. 1993 . L-ß-(2S,4S)- and L-α-(2S,4S)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships . J. Med. Chem. , 36 : 519 – 528 .
   PubMed Web of Science ®Google Scholar
• Grove , K. L. , Guo , X. , Liu , S.-H. , Gao , Z. , Chu , C. K. and Cheng , Y.-C. 1995 . Anticancer activity of ß-L-dioxolane cytidine, a novel nucleoside analogue with the unnatural L-configuration . Cancer Res. , 55 : 3008 – 3011 .
   PubMed Web of Science ®Google Scholar
• Swords , R. and Giles , F. 2007 . Troxacitabine in acute leukemia . Hematology , 12 : 219 – 227 .
   PubMed Web of Science ®Google Scholar
• Huang , M.-J. , Yang , Z.-J. , Zhang , L.-R. and Zhang , L.-H. 2009 . Design and synthesis of L-5′-noraristeromycin analogues as potent antitumor agents . J. Chin. Pharm. Sci. , 18 : 313 – 319 .
   Google Scholar
• Deagranges , C. , Razaka , G. , Drouillet , F. , Bricaud , H. , Herdewijn , P. and DeClercq , E. 1984 . Regeneration of the antiviral drug (E)-5-(2-bromovinyl)-2′-deoxyuridine in vivo . Nucleic Acids Res. , 12 : 2081 – 2090 .
   Web of Science ®Google Scholar
• Kumar , V. , Wiebe , L. I. and Knaus , E. E. 1994 . A mild and efficient methodology for the synthesis of 5-halogeno-uracil nucleosides that occurs via a 5-halogeno-6-azido-5,6-dihydro intermediate . Can. J. Chem. , 72 : 2005 – 2010 .
   Web of Science ®Google Scholar
• Wigerinck , P. , Kerremans , L. , Claes , P. , Snoeck , R. , Maudgal , P. , DeClercq , E. and Herdewijn , P. 1993 . Synthesis and antiviral activity of 5-thien-2-yl-2′-deoxyuridine analogues . J. Med. Chem. , 36 : 538 – 543 .
   PubMed Web of Science ®Google Scholar
• Wigerinck , P. , Pannecouque , C. , Snoeck , R. , Claes , P. , DeClercq , E. and Herdewijn , P. 1991 . 5-(5-bromothien-2-yl)-2′-deoxyuridine and 5-(5-chlorothien-2-yl)-2′-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2′-deoxyuridine in the inhibition of Herpes Simplex virus type 1 replication . J. Med. Chem. , 34 : 2383 – 2389 .
   PubMed Web of Science ®Google Scholar
• Holy , A. 1972 . Preparation of 2′-deoxy-L-ribonucleosides of the pyrimidine series . Collect. Czech. Chem. Commun. , 37 : 4072 – 4086 .
   Web of Science ®Google Scholar
• Kumar , V. and Malhotra , S. V. 2009 . Ionic liquid mediated synthesis of 5-halouracil nucleosides: key precursors for potential antiviral drugs . Nucleos. Nucleot. & Nucleic Acids , 28 : 821 – 834 .
   PubMed Web of Science ®Google Scholar
• Kumar , V. , Jeremy , Y. , Muroyama , A. and Malhotra , S. V. 2009 . Highly efficient method for C-5 halogenationof pyrimidine-based nucleosides in ionic liquids . Synthesis , : 3957 – 3962 . and references therein
   Web of Science ®Google Scholar
• Asakura , J. I. and Robins , M. J. 1990 . Cerium(IV)-mediated halogenation at C-5 of uracil derivatives . J. Org. Chem. , 55 : 4928 – 4933 .
   Web of Science ®Google Scholar
• Sung , W. L. 1982 . Synthesis of 1-(1,2,4-triazol-1-yl)pyrimidin-2(1H)-one ribonucleotide and its application in synthesis of oligiribonucleotides . J. Org. Chem. , 47 : 3623 – 3628 .
   Web of Science ®Google Scholar
• Liu , T.-S. , Luo , M.-Z. and Liu , M.-C. 1994 . Synthesis of 1-ß-L-arabinofuranosyl-cytosine (ß-L-ara-C) and 2′-deoxy-2′-methylene-ß-L-cytidine (ß-L-DMDC) as potential antineoplastic agents . Nucleos. Nucleot. , 13 : 1861 – 1870 .
   Google Scholar
• Riu , E. K. and MacCoss , M. 1981 . New procedure for the chlorination of pyrimidine and purine nucleosides . J. Org. Chem. , 46 : 2819 – 2823 .
   Web of Science ®Google Scholar
• Kanai , T. and Maruyama , O. 1976 . A nucleoside rearrangement, formation of 6,2′-anhydro-5-substituted isocytosine nucleosides . J. Carbohydr. Nucleos. Nucleot. , 3 : 25 – 46 .
   Google Scholar
• Kanai , T. and Ichino , M. 1972 . Pyrimidine nucleosides. 5. Synthesis of carcinostatic halogeno cyclonucleosides . J. Med. Chem. , 15 : 1218 – 1221 .
   Web of Science ®Google Scholar
• Varga , A. , Chaloin , L. , Sági , G. , Sendula , R. , Gráczer , É. , Liliom , K. , Závodszky , P. , Lionne , C. and Vas , M. 2011 . Nucleotide promiscuity of 3-phosphoglycerate kinase is in focus: implications for the design of better anti-HIV analogues . Mol. Biosystems , 7 : 1863 – 1873 .
   Web of Science ®Google Scholar
• Griffon , J.-F. , Mathe , C. , Faraj , A. , Aubertin , A.-M. , DeClercq , E. , Balzarini , J. , Sommadossi , J.-P. and Gosselin , G. 2001 . Stereospecific synthesis and biological evaluation of ß-L-pentofuranonucleoside derivatives of 5-fluoro-uracil and 5-fluoro-cytosine . Eur. J. Med. Chem. , 36 : 447 – 460 .
   Web of Science ®Google Scholar
• Slater , T. F. , Sawyer , B. and Strauli , U. 1963 . Studies on succinate-tetrazoliumreductase systems. III. Points of coupling of four different tetrazolium salts . Biochim. Biophys. Acta , 77 : 383 – 393 .
   PubMed Web of Science ®Google Scholar