Asymmetric Synthesis and Biological Activity of l-Bicyclocarba-d4T

REFERENCES

• Barre-Sinoussi , F. , Chermann , J. C. , Rey , F. , Nugeyre , M. T. , Chamaret , S. , Gruest , J. , Dauguet , C. , Axler-Blin , C. , Vezinet-Brun , F. , Rouzioux , C. , Rozenbaum , W. and Montagnier , L. 1983 . Isolation of a T-lymphotropic retrovirus from a patient at risk for acquired immune deficiency syndrome (AIDS) . Science , 220 : 868 – 871 .
   PubMed Web of Science ®Google Scholar
• De Clercq , E. 1992 . HIV inhibitors targeted at the reverse transcriptase . AIDS Res. Hum. Retroviruses , 8 : 119
   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
• Marquez , V. E. and Lim , M.-I. 1986 . Carbocyclic nucleosides . Med. Res. Rev. , 6 : 1 – 40 .
   PubMed Web of Science ®Google Scholar
• Marquez , V. E. 1996 . “ Carbocyclic nucleosides ” . In Advances in Antiviral Drug Design , Edited by: De Clercq , E. vol. 2 , 89 – 146 . Greenwich, CT : Jai Press Inc. .
   Google Scholar
• Shin , K. J. , Moon , H. R. , George , C. and Marquez , V. E. 2000 . Construction of the bicyclo[3.1.0]hexane template of a conformationally locked carbocyclic adenosine via an olefin keto-carbene cycloaddition . J. Org. Chem. , 65 : 2172 – 2178 .
   PubMed Web of Science ®Google Scholar
• Moon , H. R. , Kim , H. O. , Chun , M. W. , Jeong , L. S. and Marquez , V. E. 1999 . Synthesis of cyclo propyl-fused carbocyclic nucleosides via the regioselective opening of cyclic sulfites . J. Org. Chem. , 64 : 4733 – 4741 .
   PubMed Web of Science ®Google Scholar
• Moon , H. R. , Ford , H. Jr. and Marquez , V. E. 2000 . A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides . Org. Lett. , 2 : 3793 – 3996 .
   PubMed Web of Science ®Google Scholar
• Choi , Y. , George , C. , Comin , M. J. , Barchi , J. J. Jr. , Kim , H. S. , Jacobson , K. A. , Balzarini , J. , Boyer , P. L. , Hughes , S. H. and Marquez , V. E. 2003 . A conformationally locked analogue of the anti-HIV agent stavudine. An important correlation between pseudorotation and maximum amplitude . J. Med. Chem. , 46 : 3292 – 3299 .
   PubMed Web of Science ®Google Scholar
• Sekiyama , T. , Hatsuya , S. , Tanaka , Y. , Uchiyama , M. , Ono , N. , Iwayama , S. , Oikawa , M. , Suzuki , K. , Okunishi , M. and Tsuji , T. 1998 . Synthesis and antiviral activity of novel acyclic nucleosides: discovery of a cyclopropyl nucleoside with potent inhibitory activity against herpesviruses . J. Med. Chem. , 41 : 1284 – 1298 .
   PubMed Web of Science ®Google Scholar
• Onishi , T. , Matsuzawa , T. , Nishi , S. and Tsuji , T. 1999 . A practical synthesis of antiviral cyclopropane nucleoside A-5021 . Tetrahedron Lett. , 40 : 8845 – 8847 .
   Web of Science ®Google Scholar
• Grubbs , R. H. and Chang , S. 1998 . Recent advances in olefin metathesis and its application in organic synthesis . Tetrahedron , 54 : 4413 – 4450 .
   Web of Science ®Google Scholar
• Grubbs , R. H. 2004 . Olefin metathesis . Tetrahedron , 60 : 7117 – 7140 .
   Web of Science ®Google Scholar
• Marquez , V. E. , Russ , P. , Alons , R. , Siddiqui , M. A. , Hernandez , S. , George , C. , Nicklaus , M. C. , Dai , F. and Ford , H. Jr. 1999 . Synthesis of conformationally restricted carbocyclic nucleosides: the role of the O(4′)-atom in the key hydration step of adenosine deaminase . Helv. Chim. Acta. , 82 : 2119 – 2129 .
   Web of Science ®Google Scholar