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Synthesis and Cytotoxicity of Conjugates of Betulinic Acid and F-Containing 2-Acylcycloalkane-1,3-Diones

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Chemistry of Natural Compounds Aims and scope

Conjugates of betulinic acid with 2-(fluoroacyl)cycloalkane-1,3-dione motifs were synthesized by reacting 3-chloro-2-(fluoroacyl)-2-cycloalkene-1-ones with an equivalent amount of betulinic acid aminoalkylamide hydrochlorides in the presence of Et3N in CHCl3. Reduction of betulonic acid conjugates with 2-trifluoroacetylcyclopentane-1,3-dione by NaBH4 in THF produced betulinic acid derivatives containing 2-(1-hydroxy-2,2,2-trifluoroethyl)cyclopentane-1,3-dione. The cytotoxicity of the synthesized compounds was assessed against glioblastoma multiforme (U-87 MG) and breast cancer cell lines (MCF7).

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References

  1. D. J. Newman and G. M. Cragg, J. Nat. Prod., 70, 461 (2007).

  2. S. Choudhary, P. K. Singh, H. Verma, H. Singh, and O. Silakari, Eur. J. Med. Chem., 151, 62 (2018).

  3. J. Huang, L. Yang, C. Su, X. Chu, J. Zhang, S. Deng, and K. Cheng, Chem. Nat. Compd., 54, 106 (2018).

  4. T. S. Khlebnicova, Yu. A. Piven, A. V. Baranovsky, F. A. Lakhvich, S. V. Shishkina, D. Zicane, Z. Tetere, I. Ravina, V. Kumpins, I. Rijkure, I. Mierina, U. Peipins, and M. Turks, Steroids, 117, 77 (2017).

  5. S. Jager, H. Trojan, T. Kopp, M. N. Laszczyk, and A. Scheffler, Molecules, 14, 2016 (2009).

  6. S. C. Jonnalagadda, P. Suman, D. C. Morgan, and J. N. Seay, in: Studies in Natural Products Chemistry, Atta-ur-Rahman (ed.), Elsevier, Amsterdam, 2017, p. 45.

  7. G.-B. Xu, Y.-H. Xiao, Q.-Y. Zhang, M. Zhou, and S.-G. Liao, Eur. J. Med. Chem., 145, 691 (2018).

  8. M. G. Moghaddam, F. B. H. Ahmad, and A. Samzadeh-Kermani, Pharmacol. Pharm., 3, 119 (2012).

  9. F. A. Lakhvich and T. S. Khlebnikova, Vestsi Akad. Navuk Belarusi, Ser. Khim. Navuk, No. 4, 101 (1996).

  10. K. Nakagawa-Goto, P.-C. Wua, K. F. Bastow, S.-C. Yang, S.-L. Yu, H.-Y. Chen, J.-C. Lin, M. Goto, S. L. Morris-Natschke, P.-C. Yang, and K.-H. Lee, Bioorg. Med. Chem., 19, 1816 (2011).

  11. T. S. Khlebnikova, Yu. A. Piven′, V. G. Isakova, A. V. Baranovskii, and F. A. Lakhvich, Khim. Geterotsikl. Soedin., 53, 1254 (2017).

  12. A. Schmidt and W. Boland, J. Org. Chem., 72, 1699 (2007).

  13. Y. Zhou, J. Wang, Z. Gu, S. Wang, W. Zhu, J. L. Acena, V. A. Soloshonok, K. Izawa, and H. Liu, Chem. Rev., 116, 422 (2016).

  14. P. Jeschke, Pest Manage. Sci., 73, 1053 (2017).

  15. V. G. Isakova, T. S. Khlebnikova, and F. A. Lakhvich, Usp. Khim., 79, 929 (2010).

  16. N. I. Petrenko, N. V. Elantseva, V. Z. Petukhova, M. M. Shakirov, E. E. Shul′ts, and G. A. Tolstikov, Chem. Nat. Compd., 38, 331 (2002).

  17. T. S. Khlebnikova, Yu. A. Piven′, and F. A. Lakhvich, Chem. Nat. Compd., 53, 486 (2017).

  18. T. Mosmann, J. Immunol. Methods, 65, 55 (1983).

  19. T. S. Khlebnikova, V. G. Isakova, A. V. Baranovskii, F. A. Lakhvich, and A. S. Lyakhov, Zh. Obshch. Khim., 77, 1657 (2007).

  20. T. S. Khlebnicova, V. G. Isakova, A. V. Baranovsky, E. V. Borisov, and F. A. Lakhvich, J. Fluorine Chem., 127, 1564 (2006).

  21. T. S. Khlebnikova, Yu. A. Piven′, V. G. Isakova, and F. A. Lakhvich, Zh. Org. Khim., 48, 1283 (2012).

  22. T. S. Khlebnikova, V. G. Isakova, and F. A. Lakhvich, Zh. Obshch. Khim., 81, 261 (2011).

  23. T. S. Khlebnikova, V. G. Isakova, and F. A. Lakhvich, Zh. Org. Khim., 45, 1007 (2009).

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Acknowledgment

The work was financially supported by the National Academy of Sciences of Belarus and the Siberian Branch, Russian Academy of Sciences (Grant X15CO-001, Project 0302-2015-0003).

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 5/2 Acad. Kuprevich St., 220141, Minsk, Belarus

    T. S. Khlebnikova, Yu. A. Piven’ & F. A. Lakhvich

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, 9 Acad. Lavrent′eva Prosp., Novosibirsk, 630090, Russia

    T. S. Frolova, I. V. Sorokina & T. G. Tolstikova

Authors
  1. T. S. Khlebnikova
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  2. Yu. A. Piven’
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  3. F. A. Lakhvich
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  4. T. S. Frolova
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  5. I. V. Sorokina
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  6. T. G. Tolstikova
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Correspondence to T. S. Khlebnikova.

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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2018, pp. 936–940.

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Khlebnikova, T.S., Piven’, Y.A., Lakhvich, F.A. et al. Synthesis and Cytotoxicity of Conjugates of Betulinic Acid and F-Containing 2-Acylcycloalkane-1,3-Diones. Chem Nat Compd 54, 1100–1105 (2018). https://doi.org/10.1007/s10600-018-2565-y

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  • DOI: https://doi.org/10.1007/s10600-018-2565-y

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