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14β-(Isoxazol-3-yl)methylestrane Steroids: Chemoselective Synthesis and Transformations with Heterocyclic Ring Opening

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Abstract

Steroids containing an isoxazole, isoxazoline, or enaminocarbonyl substituent at C-14 and a C-14-C-15-fused pyrrolidine ring were synthesized. The influence of solvents on the result of dipolar cycloaddition and solvolysis of bridged nitrosteroids was evaluated. Cytotoxicity testing of estrone analogs on cancer cells of various origins revealed activity against breast, colorectal, prostate, and lung cancer cells.

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References

  1. Baranovsky, A.V., Bolibrukh, D.A., and Schneider, B., Steroids, 2015, vol.104, p.37. doi https://doi.org/10.1016/j.steroids.2015.08.009

    Article  CAS  PubMed  Google Scholar 

  2. Baranovsky, A.V., Bil’dyukevich, V.N., Golubeva, M.B., Kuzmitsky, B.B., and Mamchits, Yu.Yu., Russ. J. Bioorg. Chem., 2016, vol.42, p.83. doi https://doi.org/10.1134/S1068162015060023

    Article  CAS  Google Scholar 

  3. Pataki, J. and Siade, G., J. Org. Chem., 1972, vol.37, p.2127.

    Article  CAS  PubMed  Google Scholar 

  4. Baranovsky, A.V., Bolibrukh, D.A., Khripach, V.A., and Schneider, B., Arkivoc, 2008, vol.9, p.29. doi https://doi.org/10.3998/ark.5550190.0009.904

    Google Scholar 

  5. Baranovskii, A.V. and Golubeva, M.B., Chem. Nat. Comp., 2016, vol.52, p.856. doi https://doi.org/10.1007/s10600-016-1796-z

    Article  CAS  Google Scholar 

  6. Nicolaou, K.C., Hao, J, Reddy, M.V., Rao, P.B., Rassias, G., Snyder, S.A., Huang, X., Chen, D.Y.-K., Brenzovich, W.E., Giuseppone, N., Giannakakou, P, and O’Brate, A., J. Am. Chem. Soc., 2004, vol.126, p.12897. doi https://doi.org/10.1021/ja040093a

    Article  CAS  PubMed  Google Scholar 

  7. Kopka, I.E., Lin, L.S., Jewell, J.P., Lanza, T.J., Fong, T.M., Shen, C.-P., Lao, Z.J., Ha, S., Castonguay, L.G., Van der Ploeg, L., Goulet, M.T., and Hagmann, W.K., Bioorg. Med. Chem. Lett., 2010, vol.20, p.4757. doi https://doi.org/10.1016/j.bmcl.2010.06.127

    Article  CAS  PubMed  Google Scholar 

  8. Brewster, J.H., Comprehensive Organic Synthesis, Trost, B.M., Ed., Oxford-New York-Seoul-Tokyo: Pergamon Press. 2007, vol. 8, p. 211.

    Google Scholar 

  9. Singh, V., Vedantham, P., and Sahu, P.K., Tetrahedron, 2004, vol.60, p.8161. doi https://doi.org/10.1016/j.tet.2004.06.096

    Article  CAS  Google Scholar 

  10. Fajkos, J., Chem. Listy, 1957, vol.51, p.1894.

    CAS  Google Scholar 

  11. Yermolina, M.V., Wang, J.-Z., Caffrey, M., Rong, L.-J.L., and Wardrop, D.J., J. Med. Chem., 2011, vol.54, p.765. doi https://doi.org/10.1021/jm1008715

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Entwistle, I.D. and Wood, W.W., Comprehensive Organic Synthesis. Trost, B.M., Ed., Oxford-New York-Seoul-Tokyo: Pergamon Press. 2007, vol. 8, p. 955.

    Google Scholar 

  13. Grundmann, C. and Grunanger, P., The Nitrile Oxides, New York: Springer-Verlag, 1971.

    Book  Google Scholar 

  14. Kheruze, Yu.I., Galishev, V.A., and Petrov, Zh. Org. Khim., 1988, vol.24, p.944.

    CAS  Google Scholar 

  15. Schmitt, D.C., Lam, L., and Johnson, J.S., Org. Lett., 2011, vol.13, p.5136. doi https://doi.org/10.1021/ol202002r

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Vasil’ev, N.V., Savostin, V.S., Kolomiets, A.F., and Sokol’skii, G.A., Chem. Heterocycl. Compd., 1989, vol.25, p.555. doi https://doi.org/10.1007/BF00482506

    Article  Google Scholar 

  17. Armarego, W.L.F. and Chai, C.L.L., Purification of Laboratory Chemicals, 5th Ed. Oxford: Butterworth-Heinemann. 2003.

    Google Scholar 

  18. Scherbakov, A.M., Komkov, A.V., Komendantova, A.S., Yastrebova, M.A., Andreeva, O.E., Shirinian, V.Z., Hajra, A., Zavarzin, I.V., and Volkova, Y.A., Front Pharmacol., 2018, vol.8, p.979. doi https://doi.org/10.3389/fphar.2017.00979

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Kuprevicha 5/2, Minsk, 220147, Belarus

    A. V. Baranovsky & A. S. Ladyko

  2. Blokhin National Medical Research Center of Oncology, Kashirskoe shosse 24, Moscow, 115522, Russia

    V. A. Shatskaya & A. M. Scherbakov

Authors
  1. A. V. Baranovsky
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  2. A. S. Ladyko
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  3. V. A. Shatskaya
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  4. A. M. Scherbakov
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Corresponding authors

Correspondence to A. V. Baranovsky or A. M. Scherbakov.

Additional information

Russian Text © A.V. Baranovsky, A.S. Ladyko, V.A. Shatskaya, A.M. Scherbakov, 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 2, pp. 252–265.

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Baranovsky, A.V., Ladyko, A.S., Shatskaya, V.A. et al. 14β-(Isoxazol-3-yl)methylestrane Steroids: Chemoselective Synthesis and Transformations with Heterocyclic Ring Opening. Russ J Org Chem 55, 202–214 (2019). https://doi.org/10.1134/S107042801902012X

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  • DOI: https://doi.org/10.1134/S107042801902012X

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