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Original Articles

Inhibitors Interacting with the Magnesium Binding Site of Reverse Transcriptase: Synthesis and Biological Activity Studies of 3′-(Ω-Amino-Acyl) Amino-3′-Deoxy-Thymidine

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Pages 495-505 | Received 11 Oct 2007, Accepted 13 Mar 2008, Published online: 19 Jun 2008

REFERENCES

  • Miallau , L. , Alphey , M. S. , Kemp , L. E. , Leonard , G. A. , Mc Sweeney , S. M. , Hecht , S. , Bacher , A. , Eisenreich , W. , Rohdich , F. and Hunter , W. N. 2003 . Biosynthesis of isoprenoids: crystal structure of 4-diphosphocytidyl-2C-methyl-D-erythritol kinase . Proc. Natl. Acad. Sci. USA , 100 : 9173 – 9178 .
  • Didierjean , J. , Isel , C. , Querre , F. , Mouscadet , J.-F. , Aubertin , A-M. , Valnot , J.-Y. , Piettre , S. R. and Marquet , R. 2005 . Inhibition of human immunodeficiency virus type 1 reverse transcriptase, RNase H, and integrase activities by hydroxytropolones . Antimicrob. Agents Chemother. , 49 : 4884 – 4894 .
  • Pari , K. , Mueller , G. A. , DeRose , E. F. , Kirby , T. W. and London , R. E. 2003 . Solution structure of the RNase H domain of the HIV-1 reverse transcriptase in the presence of magnesium . Biochemistry , 42 : 639 – 650 .
  • Davies , J. F. II , Hostomska , Z. , Hostomsky , Z. , Jordan , S. R. and Matthews , D. A. 1991 . Crystal-Structure of the Ribonuclease-H Domain of HIV-1 Reverse Transcriptase . Science , 252 : 88 – 95 .
  • Huang , H. , Chopra , R. , Verdine , G. L. and Harrison , S. C. 1998 . Structure of a covalently trapped catalytic complex of HIV-I reverse transcriptase: Implications for drug resistance . Science , 282 : 1669 – 1675 .
  • Klumpp , K. , Hang , J. Q. , Rajendran , S. , Yang , Y. , Derosier , A. , In P , W. K. , Overton , H. , Parkes , K.E.B. , Cammack , N. and Martin , J. 2003 . Two-metal ion mechanism of RNA cleavage by HIV RNase H and mechanism-based design of selective HIV RNase H inhibitors . Nucleic Acids Res. , 31 : 6852 – 6859 .
  • Teplova , M. , Wallace , S. T. , Tereshko , V. , Minasov , G. , Symons , A. M. , Cook , P. D. , Manoharan , M. and Egli , M. 1999 . Structural origins of the exonuclease resistance of a zwitterionic RNA . Proc. Natl. Acad. Sci. USA , 96 : 14240 – 14245 .
  • Lee , H. , Fong , K.-L. and Vince , R. 1981 . Puromycin Analogs–Effect of Aryl-substituted Puromycin analogs on the Ribosomal peptidyltransferase Reaction . J. Med. Chem. , 24 : 304 – 308 .
  • Nguyen-Trung , N. Q. , Botta , O. , Terenzi , S. and Strazewski , P. 2003 . A practical route to 3 ‘-amino-3 ‘-deoxyadenosine derivatives and puromycin analogues . J. Org. Chem. , 68 : 2038 – 2041 .
  • Sochacka , E. , Nawrot , B. , Pankiewicz , K. W. and Watanabe , K. W. 1990 . Synthesis of 1-methyl 5-(3-azido-2,3-dideoxy-.beta.-D-erythro-pentofuranosyl)uracil and 1-methyl-5-(3-azido-2,3-dideoxy-2-fluoro-.beta.-D-arabinofuranosyl)uracil. The C-nucleoside isostere of 3′-azido-3′-deoxythymidine and its 2′-“up”-fluoro analog . J. Med. Chem. , 33 : 1995 – 1999 .
  • Lin , T.-S. and Prusoff , W. H. 1978 . Novel synthesis and biological Activity of several 5-halo-5′-amino analogs of deoxyribopyrimidine nucleosides . J. Med. Chem. , 21 : 109 – 112 .
  • Dolle , V. , Nguyen , C. H. , Legraverend , M. , Aubertin , A.-M. , Kirn , A. , Andreola , M. L. , Ventura , M. , Tarrago-Litvak , L. and Bisagni , E. 2000 . Synthesis and antiviral activity of 4-benzyl pyridinone derivatives as potent and selective non-nucleoside human immunodeficiency virus type 1 reverse transcriptase inhibitors . J. Med. Chem. , 43 : 3949 – 3962 .
  • Moulin , E. , Barluenga , S. , Totzke , F. and Winssinger , N. 2006 . Diversity-oriented synthesis of pochonins and biological evaluation against a panel of kinases . Chem. Eur. J. , 12 : 8819 – 8834 .
  • El-Kousy , S. , Pedersen , E. B. and Nielsen , C. 1994 . Synthesis and investigation of antiviral activity of 3′-O-(aminoalkyl)-thymidines and their quaternary ammonium salts . Monatsh. Chem. , 125 : 713 – 721 .
  • Abdel , A. , Abdel , A. H. , Larsen , E. , Pedersen , E. B. and Nielsen , C. 1995 . Synthesis of 3′-O-(2-aminoethyl)-2′-deoxyuriidnes . Acta Chem. Scand. , 49 : 609 – 614 .

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