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Synthesis 2004(4): 509-516  
DOI: 10.1055/s-2004-815939
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug Candidates

Changxue Lina, Hua Fu*a, Guangzhong Tub, Yufen Zhao*a
a Key Laboratory of Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Sciences and Engineering, Tsinghua University, Beijing 100084, P. R. China
e-Mail: fuhua@mail.tsinghua.edu.cn;
b Beijing Institute of Microchemistry, Beijing 100091, P. R. China
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Publication History

Received 4 December 2003
Publication Date:
03 February 2004 (online)

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Synthesis of AZT/d4T Boranophosphates as Anti-HIV Prodrug CandidatesSynthesis 2004; 2004(11): 1902-1902
DOI: 10.1055/s-2004-829155

Abstract

AZT/d4T phosphonates were synthesized by sequential condensation of AZT/d4T with the corresponding alcohols or 5′-DMT-thymidine in the presence of pivaloyl chloride. Sequential silylation, boronation, and hydrolysis in ammonium hydroxide of these phosphonates led to anti-HIV prodrug candidates AZT/d4T boranophosphates.

Key words

anti-HIV - AZT - d4T - phosphonate - boranophosphate

    References

  • 1a Ueno T. Mitsuya H. Clin. Immunother.  1995,  4:  451 
    CrossrefGoogle Scholar
  • 1b Duffy JL. Kevin NJ. Kirk BA. Chapman KT. Schleif WA. Olsen DB. Stahlhut M. Rutkowski CA. Kuo LC. Jin LX. Lin JH. Emini EA. Tata JR. Bioorg. Med. Chem. Lett.  2002,  12:  2423 
    CrossrefGoogle Scholar
  • 1c Rocheblave L. Bihel F. De Michelis C. Priem G. Courcambeck J. Bonnet B. Chermann JC. Kraus JL. J. Med. Chem.  2002,  45:  3321 
    CrossrefGoogle Scholar
  • 2a Boussard C. Doyle VE. Mahmood N. Klimkait T. Pritchard M. Gilbert IH. Eur. J. Med. Chem.  2002,  37:  883 
    CrossrefGoogle Scholar
  • 2b Zhao H. Neamati N. Sunder S. Hong HX. Wang SM. Milne GWA. Pommier Y. Burke TR. J. Med. Chem.  1997,  40:  937 
    CrossrefGoogle Scholar
  • 2c Zhang XC. Neamati N. Lee YK. Orr A. Brown RD. Whitaker N. Pommier Y. Burke TR. Bioorg. Med. Chem.  2001,  9:  1649 
    CrossrefGoogle Scholar
  • 3a Vlieghe P. Clerc T. Pannecouque C. Witvrouw M. De Clercq E. Salles JP. Kraus JL. J. Med. Chem.  2002,  45:  1275 
    CrossrefGoogle Scholar
  • 3b Wong A. Toth I. Curr. Med. Chem.  2001,  8:  1123 
    CrossrefGoogle Scholar
  • 3c Gallo JM. Adv. Drug Deliver Rev.  1994,  14:  199 
    CrossrefGoogle Scholar
  • 4a Mitsuya H. Weinhold KJ. Furman PA. Clair MH. Proc. Natl. Acad. Sci.  1985,  82:  7096 
    Google Scholar
  • 4b Rando RF. Nguyen-Ba N. Drug Discovery Today  2000,  5:  465 
    Google Scholar
  • 4c Fischl MA. Richman DD. Grieco MH. Gottlieb MSN. Engl. J. Med.  1987,  317:  185 
    Google Scholar
  • 5 Wanger CR. Iyer VV. McIntee EJ. Med. Res. Rev.  2000,  20:  417 
    Google Scholar
  • 6 Zhang R. Lu Z. Diasio C. Liu T. Soong SJ. Antimicrob. Agents Chemother.  1993,  37:  1771 
    CrossrefGoogle Scholar
  • 7a Parang K. Wiebe LI. Knaus EE. Curr. Med. Chem.  2000,  7:  995 
    Google Scholar
  • 7b Sergheraert C. Pierlot C. Tartar A. Henin Y. Lemaitre M. J. Med. Chem.  1993,  36:  826 
    Google Scholar
  • 7c Hostetler KYL. Stuhmiller M. Lenting HBM. van den Bosch H. Richman DD. J. Biol. Chem.  1990,  265:  6112 
    Google Scholar
  • 8 Pokrovsky AG. Pronayeva TR. Fedyuk NV. Shirokova EA. Khandazhinskaya AL. Tarusova NB. Karpenko IL. Krayevsky AA. Nucleosides Nucleotides Nucleic Acids  2001,  20:  767 
    CrossrefGoogle Scholar
  • 9a Porter KW. Briley JD. Shaw BR. Nucleic Acids Res.  1997,  25:  1611 
    CrossrefGoogle Scholar
  • 9b Sergueev DS. Shaw BR. J. Am. Chem. Soc.  1998,  120:  9417 
    CrossrefGoogle Scholar
  • 10 Meyer P. Schneider B. EMBO J.  2000,  19:  3520 
    CrossrefGoogle Scholar
  • 11 Hawthorne MF. Angew. Chem., Int. Ed. Engl.  1993,  32:  950 
    CrossrefGoogle Scholar
  • 12a Brian C. Peter G. Mark D. Nucleic Acids Res.  1986,  14:  5399 
    CrossrefGoogle Scholar
  • 12b Zhang X. Abad JL. Huang Q. Zheng F. Gaffney B. Jones R. Tetrahedron Lett.  1997,  38:  7135 
    CrossrefGoogle Scholar
  • 13 Jankowska J. Sobkowski M. Stawinski J. Kraszewski A. Tetrahedron Lett.  1994,  35:  3355 
    CrossrefGoogle Scholar
  • 14 Garegg PJ. Regberg T. Stawnski J. Strömberg R. Chem. Scr.  1985,  25:  280 
    Google Scholar
  • 15 Beaucage SL. Iyer RP. Tetrahedron  1993,  12:  1075 
    Google Scholar
  • 16 Busso M. Mian AM. Hahn EF. Resnick L. AIDS Res. Hum. Retroviruses  1988,  4:  449 
    CrossrefGoogle Scholar
  • 17 Shinazi RF. Sommadossi J.-P. Saalmann V. Cannon DL. Xie M.-Y. Hart GC. Smith GC. Hahn EF. Antimicrob. Agents Chemother.  1990,  34:  1061 
    CrossrefGoogle Scholar
  • 18 Sergueeva ZA. Sergueev DS. Ribeiro AA. Summers JS. Shaw BR. Helv. Chem. Acta  2000,  83:  1377 
    CrossrefGoogle Scholar
  • 19 Jankowska J. Sobkowski M. Stawinski J. Kraszewski A. Tetrahedron, Lett.  1994,  35:  3355 
    CrossrefGoogle Scholar