Skip to main content

Antiviral Activity of Some 2'-Deoxyuridine 5-Arylethynyl Derivatives

Abstract

5-(3-Perylenylethynyl)-2'-deoxyuridine was prepared by crosslinking 5-iodo-2'-deoxyuridine derivatives with 3-ethynylperylene followed by deprotection. 5-(1-Perylenylethynyl)-, 5-(3-perylenylethynyl)-, and 5-[4-(2-benzoxazolyl)phenylethynyl]-2'-deoxyuridine were found to inhibit in Vero cells the replication of type 1 herpes simplex virus and its drug-resistant strains.

This is a preview of subscription content, access via your institution.

References

  1. De Clercq, E., Meth. Find. Exp. Clin. Pharmacol., 1980, vol. 2, pp. 253–267.

    Google Scholar 

  2. Herdewijn, P.A.M.M., Antivir. Chem. Chemother., 1994, vol. 5, pp. 131–146.

    Google Scholar 

  3. De Clercq, E., Descamps, J., De Somer, P., Barr, P.J., Jones, A.S., and Walker, R.T., Proc. Natl. Acad. Sci. USA, 1979, vol. 76, pp. 2947–2951.

    Google Scholar 

  4. De Clercq, E., Descamps, J., Balzarini, J., Giziewicz, J., Barr, P.J., and Robins, M.J., J. Med. Chem., 1983, vol. 26, pp. 661–666.

    Google Scholar 

  5. McGuigan, C., Yarnold, C.J., Jones, G., Velázquez, S., Barucki, H., Brancale, A., Andrei, G., Snoeck, R., De Clercq, E., and Balzarini, J., J. Med. Chem., 1999, vol. 42, pp. 4479–4484.

    Google Scholar 

  6. McGuigan, C., Barucki, H., Blewett, S., Carangio, A., Erichsen, J.T., Andrei, G., Snoeck, R., De Clercq, E., and Balzarini, J., J. Med. Chem., 2000, vol. 44, pp. 4993–4997.

    Google Scholar 

  7. Korshun, V.A., Manasova, E.V., Balakin, K.V., Prokhorenko, I.A., Buchatskii, A.G., and Berlin, Yu.A., Bioorg. Khim., 1996, vol. 22, pp. 923–925.

    Google Scholar 

  8. Korshun, V.A., Manasova, E.V., Balakin, K.V., Malakhov, A.D., Perepelov, A.V., Sokolova, T.A., and Berlin, Yu.A., Nucleosides Nucleotides, 1998, vol. 17, pp. 1809–1812.

    Google Scholar 

  9. Malakhova, E.V., Malakhov, A.D., Kuznitsova, S.V., Varnavskii, O.P., Kadutskii, A.P., Kozhich, D.T., Korshun, V.A., and Berlin, Yu.A., Bioorg. Khim., 1998, vol. 24, pp. 688–695.

    Google Scholar 

  10. Malakhov, A.D., Malakhova, E.V., Kuznitsova, S.V., Grechishnikova, I.V., Prokhorenko, I.A., Skorobogatyi, M.V., Korshun, V.A., and Berlin, Yu.A., Bioorg. Khim., 2000, vol. 26, pp. 39–50.

    Google Scholar 

  11. Zieger, H.E., J. Org. Chem., 1966, vol. 31, pp. 2977–2981.

    Google Scholar 

  12. Classon, B. and Samuelsson, B., Acta Chem. Scand., 1985, vol. 39, pp. 501–504.

    Google Scholar 

  13. Robins, M.J. and Barr, P.J., J. Org. Chem., 1983, vol. 48, pp. 1854–1862.

    Google Scholar 

  14. Devadoss, C., Bharathi, P., and Moore, J.S., J. Am. Chem. Soc., 1996, vol. 118, pp. 9635–9644.

    Google Scholar 

  15. Galegov, G.A., Akberova, S.I., Andronova, V.L., Leont'eva, N.A., and Stroeva, O.G., Dokl. Ross. Akad. Nauk, 2000, vol. 373, pp. 404–407.

    Google Scholar 

  16. Galegov, G.A., Shobukhov, V.M., Leont'eva, N.A., and Yas'ko, M.V., Bioorg. Khim., 1997, vol. 23, pp. 906–909.

    Google Scholar 

  17. De Clercq, E., Descamps, J., Verheist, G., Walker, R.T., Jones, A.S., Torrence, P.F., and Shugar, D., J. Infect. Dis., 1980, vol. 141, pp. 563–573.

    Google Scholar 

  18. Lown, J.W., Krowicki, K., Balzarini, J., Newman, R.A., and De Clercq, E., J. Med. Chem., 1989, vol. 32, pp. 2368–2375.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. A. Galegov.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Andronova, V.L., Skorobogatyi, M.V., Manasova, E.V. et al. Antiviral Activity of Some 2'-Deoxyuridine 5-Arylethynyl Derivatives. Russian Journal of Bioorganic Chemistry 29, 262–266 (2003). https://doi.org/10.1023/A:1023936516589

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1023936516589

  • antiviral activity
  • HSV-1
  • 5-(3-perylenylethynyl)-2'-deoxyuridine
  • 5-substituted 2'-deoxyuridines
  • type 1 herpes simplex virus