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Synthesis and Antiviral Activity of Betulonic Acid Amides and Conjugates with Amino Acids

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Abstract

Betulonic acid amides with aliphatic and heterocyclic amines and with L-amino acids were synthesized by the acid chloride method. Betulonic acid amide and L-methionine derivatives of betulonic acid and its 3-oxime effectively inhibit the influenza A virus. Betulonic acid octadecylamide is active against the herpes simplex Type 1 virus. The conjugate of betulonic acid 3-oxime with L-methionine is also active toward HIV-1. The tested compounds mainly show no activity toward the ECHO6 virus, which is devoid of a coat.

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REFERENCES

  1. De Clercq, E., Drugs Res. Dev., 1999, vol. 2,no. 5, pp. 321-331.

    Google Scholar 

  2. Holz-Smith, S.L., Sun, I.C., Jin, L., Matthews, T.J., Lee, K.H., and Chen, C.H., Antimicrob. Agents Chemother., 2001, vol. 45,no. 1, pp. 60-66.

    Google Scholar 

  3. Evers, M., Poujade, C., Soler, F., Ribeill, Y., James, C., Lelievre, Y., Gueguen, J.C., Reisdorf, D., Morize, I., Pauwels, R., De Clercq, E., Henin, Y., Bousseau, A., Mayaux, J.F., Le Pecq, J.B., and Dereu, N., J. Med. Chem., 1996, vol. 39,no. 5, pp. 1056-1068.

    Google Scholar 

  4. Jeong, H.-J., Chai, H.B., Park, S.-Y, and Kim, D.S.H.L., Bioorg. Med. Chem. Lett., 1999, vol. 9, pp. 1201-1204.

    Google Scholar 

  5. Kim, D.S.H.L., Chen, Z., van Tuyen, N., Pezzuto, J.M., Qiu, S., and Lu, Z.-Z., Synth. Commun., 1997, vol. 27,no. 9, pp. 1607-1612.

    Google Scholar 

  6. Peng, C., Bodenhausen, G., Qiu, S., Fong, H.H.S., Farnsworth, N.R., Yuan, S., and Zheng, C., Magn. Res. Chem., 1998, vol. 36, pp. 267-278.

    Google Scholar 

  7. Baltina, L.A., Ryzhova, S.A., Vasil'eva, E.V., and Tolstikov, G.A., Bioorg. Khim., 1994, vol. 20, pp. 55-62.

    Google Scholar 

  8. Kurokawa, M., Basnet, P., Ohsugi, M., Hozumi, T., Kadota, S., Namba, T., Kawana, T., and Shiraki, K., J. Pharm. Exp. Ther., 1999, vol. 289, pp. 72-78.

    Google Scholar 

  9. Flekhter, O.B., Karachurina, L.T., Nigmatullina, L.R., Sapozhnikova, T.A., Baltina, L.A., Zarudii, F.S., Galin, F.Z., Spirikhin, L.V., Tolstikov, G.A., Plyasunova, O.A., and Pokrovskii, A.G., Bioorg. Khim., 2002, vol. 28, pp. 543-550.

    Google Scholar 

  10. Pezzuto, J.M. and Kim, D.S.H.L., US Patent, 5 804 575, 1998.

  11. Valterova, E., Klinot, J., and Vystrcil, A., Collect. Czech. Chem. Commun., 1983, vol. 48, pp. 649-661.

    Google Scholar 

  12. Baltina, L.A. and Tolstikov, G.A., Zh. Obshch. Khim., 1991, vol. 61, pp. 1227-1233.

    Google Scholar 

  13. Boreko, E.I., Pavlova, N.I., Zaitseva, G.V., and Mikhailopulo, I.A., Vopr. Virusol., 2001, no. 5, pp. 40-42.

    Google Scholar 

  14. Pauwels, R., Development of New Agents Against the Human Immunodeficiency Virus (Evaluation Methods, Structure-Activity Relationships and Mechanism of Action), Leuven: Katolique Universitat, 1990.

    Google Scholar 

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Correspondence to O. B. Flekhter.

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Flekhter, O.B., Boreko, E.I., Nigmatullina, L.R. et al. Synthesis and Antiviral Activity of Betulonic Acid Amides and Conjugates with Amino Acids. Russian Journal of Bioorganic Chemistry 30, 80–88 (2004). https://doi.org/10.1023/B:RUBI.0000015778.77887.f1

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  • DOI: https://doi.org/10.1023/B:RUBI.0000015778.77887.f1

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