Design, Enantiopure Synthesis, and Biological Evaluation of Novel ISO-D-2′,3′-Dideoxy-3′-Fluorothianucleoside Derivatives as a bioisostere of Lamivudine

REFERENCES

• Furman , P. A. , Fyfe , J. A. , St. Clair , M. H. , Weinhold , K. , Rideout , J. L. , Freeman , G. A. , Lehrman , S. N. , Bolognesi , D. P. , Broder , S. , Mitsuya , H. and Barry , D. W. 1986 . Phosphorylation of 3′-azido-3′-deoxythymidine and selective interaction of the 5′-triphosphate with human immunodeficiency virus reverse tranriptase . Proc. Natl. Acad. Sci. USA , 83 : 8333 – 8337 .
   PubMed Web of Science ®Google Scholar
• Faulds , D. and Brogden , R. N. 1992 . Didanosine. A review of its antiviral activity, pharmacokinetic properties and therapeutic potential in human immunodeficiency virus infection . Drugs , 44 : 94 – 116 .
   PubMed Web of Science ®Google Scholar
• Whittington , R. and Brogden , R. N. 1992 . Zalcitabine. A review of its pharmacology and clinical potential in acquired immunodeficiency syndrome (AIDS) . Drugs , 44 : 656 – 683 .
   PubMed Web of Science ®Google Scholar
• Baba , M. , Pauwels , R. , Herdewijn , P. , De Clercq , E. , Desmyter , J. and Vandeputte , M. 1987 . Both 2′,3′-dideoxythymidine and its 2′,3′-unsaturated derivative (2′,3′-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro . Biochem. Biophys. Res. Commun. , 142 : 128 – 134 .
   PubMed Web of Science ®Google Scholar
• Soudeyns , H. , Yao , S.-J. , Gao , W. , Belleau , B. , Kraus , J.-L. , Nguyen-Ba , N. , Spira , B. and Wainberg , M. A. 1991 . Anti-human immunodeficiency virus type 1 activity and in vitro toxicity of 2′-deoxy-3′-thiacytidine (BCH-189), a novel heterocyclic nucleoside analog . Antimicrob. Agents Chemother. , 35 : 1386 – 1390 .
   PubMed Web of Science ®Google Scholar
• Bamford , M. J. , Humber , C. C. and Storer , R. 1991 . Synthesis of (±)-2′-oxa-carbocyclic-2′, 3′-dideoxynucleosides as potential anti-HIV agents . Tetrahedron Lett. , 32 : 271 – 274 .
   Web of Science ®Google Scholar
• Sells , T. B. and Nair , V. 1993 . Synthetic approaches to novel isomeric dideoxynucleosides containing a chiral furanethanol carbohydrate moiety . Tetrahedron Lett. , 34 : 3527 – 3530 .
   Web of Science ®Google Scholar
• Marquez , V. E. , Tseng , C. K.-H. , Kelley , J. A. , Mitsuya , H. , Broder , S. , Roth , J. S. and Drioll , J. S. 1987 . 2′,3′-Dideoxy-2′-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV) . Biochem. Pharmacol. , 36 : 2719 – 2722 .
   PubMed Web of Science ®Google Scholar
• Martin , J. A. , Bushnell , D. J. , Duncan , I. B. , Dunsdon , S. J. , Hall , M. J. , Machin , P. J. , Merrett , J. H. , Parkes , K. E.B. , Roberts , N. A. , Thomas , G. J. , Galpin , S. A. and Kinchington , D. 1990 . Synthesis and antiviral activity of monofluoro and difluoro analogs of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1) . J. Med. Chem. , 33 : 2137 – 2145 .
   PubMed Web of Science ®Google Scholar
• Moravcova , J. , Capkova , J. and Stanek , J. 1994 . One-pot synthesis of 1,2-O-isopropylidene-α -xylofuranose . Carbohydr. Res. , 263 : 61 – 66 .
   Web of Science ®Google Scholar
• Yoshimura , Y. , Kitano , K. , Yamada , K. , Satoh , H. , Watanabe , M. , Miura , S. , Sakata , S. , Sasaki , T. and Matsuda , A. 1997 . A novel synthesis of 2′-modified 2′-deoxy-4′-thiocytidines from D-glucose . J. Org. Chem. , 62 : 3140 – 3152 .
   PubMed Web of Science ®Google Scholar
• Jeong , L. S. , Moon , H. R. , Yoo , S. J. , Lee , S. N. , Chun , M. W. and Lim , Y.-H. 1998 . Ring contraction and rearrangement of 4-thiofuranose derivatives observed during DAST fluorination in the synthesis of L-2′-“up”-fluoro-4′-thiothymidine . Tetrahedron Lett. , 39 : 5201 – 5204 .
   Web of Science ®Google Scholar
• Jeong , L. S. , Yoo , S. J. , Moon , H. R. , Kim , Y. H. and Chun , M. W. 1998 . Participation of sulfur occurred during the Mitsunobu reaction: synthesis of novel isodideoxythionucleosides . J. Chem. Soc., Perkin Trans. 1 , : 3325 – 3326 .
   Google Scholar
• Shi , J. , Du , J. , Ma , T. , Pankiewicz , K. W. , Patterson , S. E. , Tharnish , P. M. , McBrayer , T. R. , Stuyver , L. J. , Otto , M. J. , Chu , C. K. , Schinazi , R. F. and Watanabe , K. A. 2005 . Synthesis and anti-viral activity of a series of D- and L-2′ -deoxy-2′ -fluororibonucleosides in the subgenomic HCV replicon system . Bioorg. Med. Chem. , 13 : 1641 – 1652 .
   PubMed Web of Science ®Google Scholar