Application of Solid-Phase Chemistry for the Synthesis of 3′-Fluoro-3′-Deoxythymidine

REFERENCES

• Pan , X.-Z. , Qui , Z.-D. , Baron , P.A. , Gold , J. W. M. , Polsky , B. , Chou , T.-C. and Armstrong , D. 1992 . Three-drug synergistic inhibition of HIV-1 replication in vitro by 3′-fluoro-3′-deoxythymidine, recombinant soluble CD4 and recombinant interferon-alpha . AIDS Res. Hum. Retroviruses , 8 ( 3 ) : 589 – 595 .
   PubMedGoogle Scholar
• Kong , X.-B. , Zhu , Q.-Y. , Vidal , P.M. , Watanabe , K.A. , Polsky , B. , Armstrong , D. , Ostrander , M. , Lang , S.A. , Muchmore , E. and Chou , T.-C. 1992 . Comparisons of anti-human immunodeficiency virus activities, cellular transport, and plasma and intracellular pharmacokinetics of 3′-fluoro-3′-deoxythymidine . Antimicrob. Agents Chemother , 36 : 808 – 818 .
   PubMed Web of Science ®Google Scholar
• Lundgren , B. , Bottiger , D. , Ljungdahl-Stahle , E. , Norrby , E. , Stahle , L. , Wahren , B. and Orberg , B. 1991 . Antiviral effects of 3′-fluorothymidine and 3′-azidothymidine in cynomolgus monkeys infected with simian immunodeficiency virus . J. Acquir. Immune Defic. Syndr , 4 : 489 – 498 .
   PubMed Web of Science ®Google Scholar
• Matthes , E. , Lehmann , C.H. , Scholz , D. , Von Janta-Lipinski , M. , Gaerther , K. , Rosenthal , H.A. and Langen , P . 1987 . Inhibition of HIV-associated reverse transcriptase by sugar-modified derivatives of thymidine 5′-triphosphate in comparison to cellular DNA polymerases A and B . Biochem. Biophys. Res. Commun. , 148 : 78 – 85 .
   PubMed Web of Science ®Google Scholar
• Cheng , Y.C. , Dutschman , G.E. , Baston , K.F. , Sarngadharan , M.G. and Ting , R. Y.C. 1987 . Human immunodeficiency virus reverse transcriptase: general properties and its interactions with nucleotide triphosphate analogs . J. Biol. Chem. , 262 : 2187 – 2189 .
   PubMed Web of Science ®Google Scholar
• Kim , E.Y. , Vrang , L. , Oberg , B. and Merigan , T.C. 2001 . Anti-HIV type 1 activity of 3′-fluoro-3′-deoxythymidine for several different multi-drug-resistant mutants . AIDS Res. Hum. Retroviruses , 17 : 401 – 407 .
   PubMed Web of Science ®Google Scholar
• Hoshi , A. and Castaner , J. 1994 . Alovudine . Drugs Future , 19 : 221 – 224 .
   Google Scholar
• Calvez , V. , Tubiana , R. , Ghosn , J. , Wirden , M. , Marcelin , A.G. , Westling , C. , Shoen , H. , Harmenberg , J. , Mardh , G. , Oberg , B. and Katlama , C. 2002 . MIV-310 reduces markedly viral load in patients with virological failure despite multiple-drug therapy: Results from a 4-week phase II study . Antiviral Therapy , 7 : S4 Abs
   Web of Science ®Google Scholar
• Rusconi , S. 2003 . Alovudine Medivir . Curr. Opin. Invest. Drugs , 4 : 219 – 223 .
   PubMedGoogle Scholar
• Seitz , U. , Wagner , M. , Neumaier , B. , Wawra , E. , Glatting , G. , Leder , G. , Schmid , R.M. and Reske , S.N. 2002 . Evaluation of pyrimidine metabolising enzymes and in vitro uptake of 3′-[(18)F]fluoro-3′-deoxythymidine ([(18)F]FLT) in pancreatic cancer cell lines . Eur. J. Nucl. Med. Mol. Imaging , 29 : 1174 – 1181 .
   PubMed Web of Science ®Google Scholar
• Wagner , M. , Seitz , U. , Buck , A. , Neumaier , B. , Schultheiss , S. , Bangerter , M. , Bommer , M. , Leithauser , F. , Wawra , E. , Munzert , G. and Reske , S.N. 2003 . 3′-[18F]fluoro-3′-deoxythymidine ([18F]-FLT) as positron emission tomography tracer for imaging proliferation in a murine B-Cell lymphoma model and in the human disease . Cancer Res. , 63 : 2681 – 2687 .
   PubMed Web of Science ®Google Scholar
• Shields , A.F. , Grierson , J.R. , Dohmen , B.M. , Machulla , H.J. , Stayanoff , J.C. , Lawhorn-Crews , J.M. , Obradovich , J.E. , Muzik , O. and Mangner , T.J. 1998 . Imaging proliferation in vivo with [F-18]FLT and positron emission tomography . Nature Med , 4 : 1334 – 1336 .
   PubMed Web of Science ®Google Scholar
• Wodarski , C. , Eisenbarth , J. , Weber , K. , Henze , M. and Haberkorn , U. 2000 . Eisenhut, M. Synthesis of 3′-deoxy-3′-[18F]fluoro-thymidine with 2,3′-O-anhydro-5′-O-(4,4′-dimethoxy-trityl)thymidine . J. Lab. Compd. Radiopharm. , 43 : 1211 – 1218 .
   Web of Science ®Google Scholar
• Herdewijn , P. , Balzarini , J. , De Clercq , E. , Pauwels , R. , Baba , M. , Broder , S. and Vanderhaeghe , H. 1987 . 3′-Substituted 2′,3′-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents . J. Med. Chem. , 30 : 1270 – 1278 .
   PubMed Web of Science ®Google Scholar
• Sahlberg , C. 1992 . Synthesis of 3′-ethynylthymidine, 3′-vinylthymidine and 3′-bromovinylthymidine as potential antiviral agents . Tetrahedron Lett. , 33 : 679 – 682 .
   Web of Science ®Google Scholar
• Hager , M.W. and Liotta , D.C. 1992 . An efficient synthesis of 3′-fluoro-3′-deoxythymidine (FLT) . Tetrahedron Lett. , 33 : 7083 – 7086 .
   Web of Science ®Google Scholar
• Kumar , P. , Ohkura , K. , Balzarini , J. , DeClercq , E. , Seki , K. and Wiebe , L.I. 2004 . Synthesis and antiviral activity of novel fluorinated 2′,3′-dideoxynucleosides . Nucleosides Nucleotides Nucleic Acids , 23 : 7 – 29 .
   PubMed Web of Science ®Google Scholar
• Yun , M. , Oh , S.J. , Ha , H.-J. , Ryu , J.S. and Moon , D.H. 2003 . High radiochemical yield synthesis of 3′-deoxy-3′-[18F]fluorothymidine using (5′-O-dimethoxytrityl-2′-deoxy-3′-O-nosyl-β-D-threo pentofuranosyl)thymine and its 3-N-BOC-protected analogue as a labeling precursor . Nuclear Med. Biol. , 30 : 151 – 157 .
   PubMed Web of Science ®Google Scholar