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Synthetic Transformations of Higher Terpenoids. XXXV.* Synthesis and Cytotoxicity of Macroheterocyclic Compounds Based on Lambertianic Acid

Chemistry of Natural Compounds Aims and scope

(17R)-17,18-Dipropargyloxylabda-13,15-diene was synthesized and underwent Cu-catalyzed cycloaddition with 1,10-diazodecane or 1,2-bis(2-azidoethoxy)ethane to produce macroheterocycles of the furanolabdanoid decalin fragment. The macroheterocyclic labdanoids showed significant cytotoxicity in MEL-8, MT-4, and U-937 human tumor cell models.

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References

  1. M. A. Timoshenko, A. B. Ayusheev, Yu. V. Kharitonov, M. M. Shakirov, and E. E. Shul ts, Chem. Nat. Compd., 50, 673 (2014).

  2. X. Geng, M. L. Miller, S. Lin, and I. Ojima, Org. Lett., 5, 3733 (2003).

    Article  CAS  PubMed  Google Scholar 

  3. L. Sun, X. Geng, R. Geney, Y. Li, C. Simmerling, Z. Li, J. W. Lauher, S. Xia, S. B. Horwitz, J. M. Veith, P. Pera, R. J. Bernacki, and I. Ojima, J. Org. Chem., 73, 9584 (2008).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. I. Ojima, K. Kumar, D. Awasthi, and J. G. Vineberg, Bioorg. Med. Chem., 22, 5060 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. M. Gavagnin, M. Carbone, P. Amodeo, E. Mollo, R. M. Vitale, V. Roussis, and G. Cimino, J. Org. Chem., 72, 5625 (2007).

    Article  CAS  PubMed  Google Scholar 

  6. M. Carbone, M. Gavagnin, E. Mollo, M. Bidello, V. Roussis, and G. Cimino, Tetrahedron, 64, 191 (2008).

    Article  CAS  Google Scholar 

  7. O. V. Andreeva, R. R. Sharipova, B. F. Garifullin, I. Yu. Strobykina, and V. E. Kataev, Chem. Nat. Compd., 51, 689 (2015).

    Article  CAS  Google Scholar 

  8. B. F. Garifullin, R. R. Sharipova, I. Yu. Strobykina, O. V. Andreeva, M. A. Kravchenko, and V. E. Kataev, Zh. Org. Khim., 51, 1517 (2015) [B. F. Garifullin, R. R. Sharipova, I. Yu. Strobykina, O. V. Andreeva, M. A. Kravchenko, and V. E. Kataev, Russ. J. Org. Chem., 51, 1488 (2015)].

  9. C. Wang, D. Ikhlef, S. Kahlal, J.-Y. Saillard, and D. Astruc, Coord. Chem. Rev., 316, 1 (2016).

    Article  CAS  Google Scholar 

  10. K. Kasprzak, I. Skiera, M. Piasecka, and Z. Paryzek, Chem. Rev., 116, 5689 (2016).

    Article  Google Scholar 

  11. Yu. V. Kharitonov, E. E. Shul ts, M. M. Shakirov, M. A. Pokrovskii, A. G. Pokrovskii, and G. A. Tolstikov, Izv. Akad. Nauk, Ser. Khim., 2046 (2013).

  12. G. F. Reta, A. I. Chiaramello, C. Garcia, L. G. Leon, V. S. Martin, J. M. Padron, C. E. Tonn, and O. J. Donadel, Eur. J. Med. Chem., 67, 28 (2013).

    Article  CAS  PubMed  Google Scholar 

  13. M. W. Pertino, C. Theoduloz, M. Bastias, and G. Schmeda-Hirschmann, Molecules, 18, 5936 (2013).

    Article  PubMed  Google Scholar 

  14. C. Ding, Y. Zhang, H. Chen, C. Wild, T. Wang, M. A. White, Q. Shen, and J. Zhou, Org. Lett., 15, 3718 (2013).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. R. N. Khaybullin, M. Zhang, J. Fu, X. Liang, T. Li, A. R. Katritzky, P. Okunieff, and X. Qi, Molecules, 19, 18676 (2014).

    Article  PubMed  Google Scholar 

  16. M. W. Pertino, V. Verdugo, C. Theoduloz, and G. Schmeda-Hirschmann, Molecules, 19, 2523 (2014).

    Article  PubMed  Google Scholar 

  17. E. E. Shul ts, M. E. Mironov, and Yu. V. Kharitonov, Chem. Nat. Compd., 50, 2 (2014).

  18. S. V. Chernov, E. E. Shul ts, M. M. Shakirov, and G. A. Tolstikov, Russ. J. Org. Chem., 38, 665 (2002).

  19. X. Creary, A. Anderson, C. Brophy, F. Crowell, and Z. Funk, J. Org. Chem., 77, 8756 (2012).

    Article  CAS  PubMed  Google Scholar 

  20. M. E. Mironov, M. A. Pokrovsky, Yu. V. Kharitonov, M. M. Shakirov, A. G. Pokrovsky, and E. E. Shults, ChemistrySelect, 1, 417 (2016).

    Article  CAS  Google Scholar 

  21. 21. T. G. Tolstikova, N. V. Sorokina, M. P. Dolgikh, S. V. Chernov, Yu. V. Kharitonov, E. E. Shul’ts, and G. A. Tolstikov, Khim.-farm. Zh., 39, 46 (2004).

  22. Yu. V. Kharitonov, M. M. Shakirov, and E. E. Shults, J. Inclusion Phenom. Macrocyclic Chem., 84, 197 (2016).

    Article  CAS  Google Scholar 

  23. A. R. Katritzky, N. K. Meher, S. Hanci, R. Gyanda, S. R. Tala, S. Mathai, R. S. Duran, S. Bernar, F. Sabri, S. K. Singh, J. Doskocz, and D. A. Ciaramitaro, J. Polym. Sci., Part A: Polym. Chem., 46, 238 (2008).

  24. E. Klein, S. De Bonis, B. Thiede, D. A. Skoufias, F. Kozielski, and L. Lebeau, Bioorg. Med. Chem., 15, 6474 (2007).

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

The work was supported financially by Russian Scientific Foundation Grant No. 14-13-00822. Analytical and spectral studies were performed at the Khimiya Center for Collective Use, SB, RAS.

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Correspondence to E. E. Shul’ts.

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*For No. XXXIV, see the literature [1].

Translated from Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2017, pp. 65–70. Original article submitted May 2, 2016.

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Kharitonov, Y.V., Shakirov, M.M., Pokrovskii, M.A. et al. Synthetic Transformations of Higher Terpenoids. XXXV.* Synthesis and Cytotoxicity of Macroheterocyclic Compounds Based on Lambertianic Acid. Chem Nat Compd 53, 77–82 (2017). https://doi.org/10.1007/s10600-017-1915-5

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