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Synthesis of anti-HIV nucleoside conjugates with lipophilic diol compounds

  • Drug Synthesis Methods and Manufacturing Technology
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Abstract

Synthesis of anti-HIV nucleoside lipophilic derivatives with diol compounds in which two antiviral pharmacophore residues are linked by a single hydrophobic fragment is described. It is suggested to use 2,3,4,5-tetra-O-benzyl-D, L-iditol and 1,12-dodecanediol as hydrophobic transport systems. Succinic and phosphodiester fragments were used for binding molecular units in the target conjugates.

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References

  1. P. Huang, D. Farquhar, and W. Plunkett, J. Biol. Chem., 265(20), 11914–11918 (1990).

    Google Scholar 

  2. D. M. Huryn and M. Okabe, Chem. Rev., 92(8), 1745–1768 (1992).

    Article  CAS  Google Scholar 

  3. E. De Clercq, J. Med. Chem., 38(14), 2491–2517 (1995).

    Article  PubMed  Google Scholar 

  4. K. Parang, L. I. Wiebe, and E. E. Knaus, J. Pharm. Pharm. Sci., 1(3), 108–114 (1998).

    PubMed  CAS  Google Scholar 

  5. K. Parang, L. Weibe, and E. E. Knaus, J. Cur. Med. Chem., 7(10), 995–1039 (2000).

    CAS  Google Scholar 

  6. H. Mitsuya and S. Broder, Nature, 325, 773 (1987).

    Article  PubMed  CAS  Google Scholar 

  7. K. Y. Hostetler, L. M. Stuhmiller, H. B. M. Lenting, et al., J. Biol. Chem., 265(11), 6112–6117 (1990).

    PubMed  CAS  Google Scholar 

  8. C. McGuigan, R. N. Pathirana, N. Mahmood, et al., Antivir. Res., 17(4), 311–321 (1992).

    Article  PubMed  CAS  Google Scholar 

  9. E. T. Hall, J.-P. Yan, P. Melancon, et al., J. Biol. Chem., 269(20), 14355–14358 (1994).

  10. D. Bonnaffe, B. Dupraz, J. Ughetto-Monfrin, et al., J. Org. Chem., 61(3), 895–902 (1996).

    Article  CAS  Google Scholar 

  11. C. Meier, M. Lorey, E. De Clerq, et al., J. Med. Chem., 41(9), 1417–1427 (1998).

    Article  PubMed  CAS  Google Scholar 

  12. M. H. St. Clair, J. L. Martin, G. Tudor-Williams, et al., Science, 253, 1557–1559 (1991).

    Article  PubMed  CAS  Google Scholar 

  13. T. Kawaguchi, T. Endoh, T. Seki, et al., J. Pharm. Sci., 80, 404–405 (1991).

    Article  PubMed  CAS  Google Scholar 

  14. J. M. Bailey, K. A. Nelson, M. Lightfoote, et al., Biochem. Soc. Trans., 26(4), S390 (1998).

    PubMed  CAS  Google Scholar 

  15. T. Seki, T. Kawaguchi, and K. Juni, Pharm. Res., 7, 948–952 (1990).

    Article  PubMed  CAS  Google Scholar 

  16. A. Q. Siddiqui, C. Ballatore, C. McGuigan, et al., J. Med. Chem., 42(20), 4122–4128 (1999).

    Article  PubMed  CAS  Google Scholar 

  17. A. Q. Siddiqui, C. Ballatore, C. McGuigan, et al., J. Med. Chem., 42(3), 393–399 (1999).

    Article  PubMed  CAS  Google Scholar 

  18. J. Dessolin, P. Galea, P. Vlieghe, et al., J. Med. Chem., 42(2), 229–241 (1999).

    Article  PubMed  CAS  Google Scholar 

  19. H. Schott, P. S. Ludwig, A. Immelmann, et al., Eur. J. Med. Chem., 34(4), 343–352 (1999).

    Article  CAS  Google Scholar 

  20. S. T. Jan, M. J. Shin, T. K. Venkatachalam, et al., Antivir. Chem. Chemother., 10(1), 39–46 (1999).

    PubMed  CAS  Google Scholar 

  21. G. L. Kucera, C. L. Goff, N. Iyer, et al., Antivir. Res., 50(2), 129–137 (2001).

    Article  PubMed  CAS  Google Scholar 

  22. T. Mavromoustakos, T. Calogeropoulou, M. Koufaki, et al., J. Med. Chem., 44(11), 1702–1709 (2001).

    Article  PubMed  CAS  Google Scholar 

  23. H. Matsumoto, T. Kimura, T. Hamawaki, et al., Bioorg. Med. Chem., 9(6), 1589–1600 (2001).

    Article  PubMed  CAS  Google Scholar 

  24. E. M. Orekhova, I. N. Gracheva, B. A. Klyashchitskii, et al., Zh. Org. Khim., 29(11), 1754–1757 (1993).

    CAS  Google Scholar 

  25. P. Buchwald and N. Bodor, Pharmazie., 57(2), 87–93 (2002).

    PubMed  CAS  Google Scholar 

  26. N. M. Mahfouz and M. A. Hassan, J. Pharm. Pharmacol., 53(6), 841–848 (2001).

    Article  PubMed  CAS  Google Scholar 

  27. J. Takata, Y. Karube, Y. Nagata, et al., J. Pharm. Sci., 84, 96–100 (1995).

    Article  PubMed  CAS  Google Scholar 

  28. Yu. V. Berezovskaya, M. V. Chudinov, Yu. G. Kirillova, et al., Nucleosides & Nucleotides., 17, 2127–2133 (1998).

    CAS  Google Scholar 

  29. R. J. Jones and N. Bischofberger, Antiviral Res., 27(1, 2), 1–17 (1995).

    Article  PubMed  CAS  Google Scholar 

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 40, No. 5, pp. 41–45, May, 2006.

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Tuchnaya, O.A., Elizarova, S.N., Sharikova, S.A. et al. Synthesis of anti-HIV nucleoside conjugates with lipophilic diol compounds. Pharm Chem J 40, 276–280 (2006). https://doi.org/10.1007/s11094-006-0108-5

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  • DOI: https://doi.org/10.1007/s11094-006-0108-5

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