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Conjugates of several lupane, oleanane, and ursane triterpenoids with the antituberculosis drug isoniazid and pyridinecarboxaldehydes

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Chemistry of Natural Compounds Aims and scope

Conjugates of betulinic, oleanolic, ursolic, and glycyrrhetic acids and several of their derivatives with the antituberculosis drug isoniazid and 3- and 4-pyridinecarboxaldehydes were synthesized.

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References

  1. O. B. Flekhter, O. Yu. Ashavina, E. I. Boreko, L. T. Karachurina, N. I. Pavlova, N. N. Kabal’nova, O. V. Savinova, F. Z. Galin, S. N. Nikolaeva, F. S. Zarudii, L. A. Baltina, and G. A. Tolstikov, Khim.-farm. Zh., 36, No. 6, 21 (2002).

    Google Scholar 

  2. L. A. Baltina, O. B. Flekhter, L. R. Nigmatullina, E. I. Boreko, N. I. Pavlova, S. N. Nikolaeva, O. V. Savinova, and G. A. Tolstikov, Bioorg. Med. Chem. Lett., 13, 3549 (2003).

    Article  PubMed  CAS  Google Scholar 

  3. O. B. Kazakova, G. V. Giniyatullina, E. Y. Yamansarov, and G. A. Tolstikov, Bioorg. Med. Chem. Lett., 20, 4088 (2010).

    Article  PubMed  CAS  Google Scholar 

  4. A. Sami, M. Tarua, K. Salme, and Y.-K. Jari, Eur. J. Pharm. Sci., 29, 1 (2006).

    Article  Google Scholar 

  5. O. B. Flekhter, N. I. Medvedeva, O. S. Kukovinets, L. V. Spirikhin, E. G. Galkin, F. Z. Galin, D. G. Golovanov, N. I. Pavlova, O. V. Savinova, E. I. Boreko, and G. A. Tolstikov, Bioorg. Khim., 6, 629 (2007).

    Google Scholar 

  6. O. B. Flekhter, N. I. Medvedeva, G. A. Tolstikov, O. V. Savinova, E. I. Boreko, and F. M. Dolgushin, Bioorg. Khim., 35, 129 (2009).

    PubMed  CAS  Google Scholar 

  7. V. E. Kataev, I. Yu. Strobykina, O. V. Andreeva, B. F. Garifullin, R. R. Sharipova, V. F. Mironov, and R. V. Chestnova, Bioorg. Khim., 37, 542 (2011).

    PubMed  CAS  Google Scholar 

  8. J. Q. Gu, Y. Wang, S. Franzblau, G. Montenegro, D. Yang, and B. N. Timmermann, Planta. Med., 70, 509 (2004).

    Article  PubMed  CAS  Google Scholar 

  9. S. Suksamrarn, P. Panseeta, S. Kunchanawatta, T. Distaporn, S. Ruktasing, and A. Suksamrarn, Chem. Pharm. Bull., 54, 535 (2006).

    Article  PubMed  CAS  Google Scholar 

  10. T. Tanachatchairatana, J. B. Bremner, R. Chokchaisiri, and A. Suksamrarn, Chem. Pharm. Bull., 56, 194 (2008).

    Article  PubMed  CAS  Google Scholar 

  11. A. Jimenez-Arellanes, M. Meckes, J. Torres, and J. L. Herrera, J. Ethnopharmacol., 111, 202 (2007).

    Article  PubMed  CAS  Google Scholar 

  12. B. U. Jaki, S. G. Franzblau, L. R. Chadwick, D. C. Lankin, F. Zhang, Y. Wang, and G. F. Pauli, J. Nat. Prod., 71, 1742 (2008).

    Article  PubMed  CAS  Google Scholar 

  13. F. Ge, F. Zeng, S. Liu, N. Guo, H. Ye, Y. Song, J. Fan, X. Wu, X. Wang, X. Deng, Q. Jin, and L. Yu, J. Med. Microbiol., 59, 567 (2010).

    Article  PubMed  CAS  Google Scholar 

  14. A. Jimenez, M. Meckes, V. Alvarez, J. Torres, and R. Parra, Phytother. Res., 19, 320 (2005).

    Article  PubMed  CAS  Google Scholar 

  15. O. B. Flekhter, E. I. Boreko, L. R. Nigmatullina, E. V. Tret_yakova, N. I. Pavlova, L. A. Baltina, S. N. Nikolaeva, O. V. Savinova, V. F. Eremin, F. Z. Galin, and G. A. Tolstikov, Bioorg. Khim., 30, 89 (2004).

    PubMed  CAS  Google Scholar 

  16. O. B. Flekhter, E. I. Boreko, L. R. Nigmatullina, N. I. Pavlova, S. N. Nikolaeva, O. V. Savinova, V. F. Eremin, L. A. Baltina, F. Z. Galin, and G. A. Tolstikov, Bioorg. Khim., 29, 326 (2003).

    PubMed  CAS  Google Scholar 

  17. O. B. Flekhter, L. T. Karachurina, L. R. Nigmatullina, L. A. Baltina, F. S. Zarudii, V. A. Davydova, L. V. Spirikhin, I. P. Baikova, F. Z. Galin, and G. A. Tolstikov, Khim.-farm. Zh., 34, No. 2, 3 (2000).

    Google Scholar 

  18. O. B. Flekhter, L. R. Nigmatullina, L. A. Baltina, L. T. Karachurina, F. Z. Galin, F. S. Zarudii, G. A. Tolstikov, E. I. Boreko, N. I. Pavlova, S. N. Nikolaeva, and O. V. Savinova, Khim.-farm. Zh., 36, No. 9, 26 (2002).

    Google Scholar 

  19. G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, and T. G. Tolstikova, Licorice: Biovariety, Chemistry, and Use in Medicine [in Russian], Akad. Izd. Geo, Novosibirsk, 2007.

    Google Scholar 

  20. O. B. Flekhter, E. I. Boreko, L. R. Nigmatullina, N. I. Pavlova, N. I. Medvedeva, S. N. Nikolaeva, E. V. Tret_yakova, O. V. Savinova, L. A. Baltina, L. T. Karachurina, F. Z. Galin, F. S. Zarudii, and G. A. Tolstikov, Khim.-farm. Zh., 38, No. 3, 31 (2004).

    Google Scholar 

  21. N. P. Buu-Hoi, N. D. Xuong, N. H. Nam, F. Binon, and R. Royer, J. Chem. Soc., 1358 (1953).

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Acknowledgment

The work was supported financially by the RAS Presidium Program No. 5 “Fundamental Science in Medicine” (topic “Creation of a New Class of Highly Effective and Nontoxic Antituberculosis Agents Based on Higher Terpenoids, Their Glycosides and Polysaccharides”) and a grant of the RF President for State Support of Young Russian Scientists (MK-7360.2010.3). We thank the National Institute of Allergy and Infectious Diseases (NIAID, USA) for studying the antituberculosis activity (strain H37Rv in vitro) of 7–9, 15–18, 20, 22, 23, 25, 26, 30, and 31.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Prosp. Oktyabrya, 71, 450054, Ufa, Russia

    O. B. Kazakova, N. I. Medvedeva, I. A. Samoilova, I. P. Baikova & G. A. Tolstikov

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 420088, Kazan, Russia

    V. E. Kataev & V. F. Mironov

Authors
  1. O. B. Kazakova
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  2. N. I. Medvedeva
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  3. I. A. Samoilova
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  4. I. P. Baikova
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  5. G. A. Tolstikov
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  6. V. E. Kataev
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  7. V. F. Mironov
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Corresponding author

Correspondence to O. B. Kazakova.

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Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2011, pp. 661–666.

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Kazakova, O.B., Medvedeva, N.I., Samoilova, I.A. et al. Conjugates of several lupane, oleanane, and ursane triterpenoids with the antituberculosis drug isoniazid and pyridinecarboxaldehydes. Chem Nat Compd 47, 752–758 (2011). https://doi.org/10.1007/s10600-011-0050-y

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  • DOI: https://doi.org/10.1007/s10600-011-0050-y

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