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Synthesis and some biological properties of sulfamates derived from 8α-analogs of steroidal estrogens

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Abstract

Sulfamates derived from estrogens of the 8α-series have been synthesized, and their effect on the growth of MCF-7 breast cancer cells has been studied. The best anticancer effect has been found for 7β-methyl-D-homo-6-oxa-8α-estrone sulfamate and 3-methoxy-2,17β-sulfamoyloxy-8α-estra-1,3,5(10)-triene which almost completely inhibit the growth of cancer cells.

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References

  1. Parkin, D.M., Bray, F., Ferlay, J., and Pisani, P., CA Cancer J. Clin., 2005, vol. 55, p. 74.

    Article  Google Scholar 

  2. Fischer, D.S., Allan, G.M., Bubert, C., Vicker, V., Smith, A., Tutill, H.J., Purohit, A., Wood, L., Packham, G., Mahon, M.E., Reed, M.J., and Potter, B.V.L., J. Med. Chem., 2005, vol. 48, p. 5749.

    Article  CAS  Google Scholar 

  3. Yue, W., Yager, J.D., Wang, J.-P., Jupe, E.R., and Santen, R.J., Steroids, 2013, vol. 78, p. 161.

    Article  CAS  Google Scholar 

  4. Jordan, V.C., J. Med. Chem., 2003, vol. 46, p. 1081.

    Article  CAS  Google Scholar 

  5. Fabian, C.J. and Kimler, B.F., J. Clin. Oncol., 2005, vol. 23, p. 1644.

    Article  CAS  Google Scholar 

  6. Day, J.M., Purohit, A., Tutill, H.J., Foster, P.A., Woo, L.W., Potter, B.V., and Reed, M.J., Ann. N.Y. Acad. Sci., 2009, vol. 1155, p. 80.

    Article  CAS  Google Scholar 

  7. Maltais, R. and Poirier, D., Steroids, 2011, vol. 76, p. 929.

    Article  CAS  Google Scholar 

  8. Geisler, J., Sasano, H., Chen, S., and Purohit, A., J. Steroid Biochem. Mol. Biol., 2011, vol. 125, p. 39.

    Article  CAS  Google Scholar 

  9. Mostafa, Y.A. and Taylor, S.D., J. Steroid Biochem. Mol. Biol., 2013, vol. 137, p. 183.

    Article  CAS  Google Scholar 

  10. Gupta, A., Kumar, B.S., and Negi, A.S., J. Steroid Biochem. Mol. Biol., 2013, vol. 137, p. 242.

    Article  CAS  Google Scholar 

  11. Pasqualini, J.R. and Chetrite, G.S., J. Steroid Biochem. Mol. Biol., 1999, vol. 69, p. 287.

    Article  CAS  Google Scholar 

  12. Reed, M.J., Purohit, A., Woo, L.W.L., Newman, S.P., and Potter, B.V.L., Endocrine Rev., 2005, vol. 26, p. 171.

    Article  CAS  Google Scholar 

  13. Purohit, A., Vernon, K.A., Hummelinck, A.E.W., Woo, L.L., Hejaz, H.A.M., Potter, B.V.L., and Reed, M.J., J. Steroid Biochem. Mol. Biol., 1998, vol. 64, p. 269.

    Article  CAS  Google Scholar 

  14. Li, P.-K., Chu, G.-H., Guo, J.P., Peters, A., and Selcer, K.W., Steroids, 1998, vol. 63, p. 425.

    Article  CAS  Google Scholar 

  15. Numazawa, M., Tominaga, T., Watari, Y., and Tada, Y., Steroids, 2006, vol. 71, p. 371.

    Article  CAS  Google Scholar 

  16. Woo, L.W., Bubert, C., Sutcliffe, O.B., Smith, A., Chander, S.K., Mahon, M.F., Purohit, A., Reed, M.J., and Potter, B.V., J. Med. Chem., 2007, vol. 50, p. 3540.

    Article  CAS  Google Scholar 

  17. Lawrence, H.R., Wicker, N., Allan, G.M., Smith, A., Mahon, M.F., Tutill, H.J., Purohit, A., Reed, M.J., and Potter, B.V.L., J. Med. Chem., 2005, vol. 48, p. 2759.

    Article  CAS  Google Scholar 

  18. Day, J.M., Newman, S.P., Comninos, A., Solomon, C., Purohit, A., Leese, M.P., Potter, B.V.L., and Reed, M.J., J. Steroid Biochem. Mol. Biol., 2003, vol. 84, p. 317.

    Article  CAS  Google Scholar 

  19. Hernandez-Guzman, F.G., Higashiyama, T., Pangborn, W., Osawa, Y., and Ghosh, D., J. Biol. Chem., 2003, vol. 278, p. 22 989.

    Article  CAS  Google Scholar 

  20. Boivin, R.P., Labrie, F., and Poirier, D., Steroids, 1999, vol. 64, p. 825.

    Article  CAS  Google Scholar 

  21. Bovin, R.P. and Luu-The, R., J. Med. Chem., 2000, vol. 43, p. 4465.

    Article  Google Scholar 

  22. Fischer, D.S., Chander, S.K., Woo, L.W.L., Fenton, J.C., Purohit, A., Reed, M.J., and Potter, B.V.L., J. Steroid Biochem. Mol. Biol., 2003, vol. 84, p. 343.

    Article  CAS  Google Scholar 

  23. Fischer, D.S., Woo, L.W.L., Mahon, M.F., Purohit, A., Reed, M.J., and Potter, B.V.L., Bioorg. Med. Chem., 2003, vol. 11, p. 1685.

    Article  CAS  Google Scholar 

  24. Shavva, A.G., Selivanov, S.I., Starova, G.L., Boronoeva, T.R., Ishchenko, I.V., Gluzdikov, I.A., Sharetskii, A.N., Isaeva, V.G., and Surinov, B.P., Russ. J. Bioorg. Chem., 2002, vol. 28, no. 3, p. 215.

    Article  CAS  Google Scholar 

  25. Shavva, A.G., Starova, G.L., Selivanov, S.I., and Morozkina, S.N., Chem. Heterocycl. Compd., 2008, vol. 44, no. 2, p. 148.

    Article  CAS  Google Scholar 

  26. Bogautdinov, R.P., Drozdov, A.S., Morozkina, S.N., and Shavva, A.G., Abstracts of Papers, 2nd Congress on Steroid Research, Chicago, USA, 2013, p. 41.

    Google Scholar 

  27. Fuhrman, B.J., Schairer, C., Gail, M.H., Boyd-Morin, J., Xu, X., Sue, L.Y., Buys, S.S., Isaacs, C., Keefer, L.K., Veenstra, T.D., Berg, C.D., Hoover, R.N., and Ziegler, R.G., J. Natl. Cancer Inst., 2012, vol. 104, no. 4, p. 326.

    Article  CAS  Google Scholar 

  28. Ananchenko, S.N., Limanov, V.Ye., Leonov, V.N., and Torgov, I.V., Tetrahedron, 1962, vol. 18, p. 1355.

    Article  CAS  Google Scholar 

  29. Eliseev, I.I., Andreeva, E.N., Kameneva, I.Yu., and Shavva, A.G., Vestn. Leningr. Gos. Univ., Ser. 4, 1991, no. 4, p. 74.

    Google Scholar 

  30. Morozkina, S.N., Antimonova, O.I., Drozdov, A.S., Bogautdinov, R.P., and Shavva, A.G., Vestn. Sankt-Peterb. Gos. Univ., Ser. 4, 2012, no. 3, p. 128.

    Google Scholar 

  31. Shavva, A.G., Ishchenko, I.V., Eliseev, I.I., Abusalimov, Sh.N., and Gasparyan, E.G., RF Patent no. 2 057 140, 1996; Byull. Izobret., 1996, no. 9.

    Google Scholar 

  32. Morozkina, S.N., Chentsova, A.S., Hasan, T.Yu., Selivanov, S.I., Shavarda, A.L., and Shavva, A.G., Chem. Heterocycl. Compd., 2009, vol. 45, no. 9, p. 1144.

    Article  CAS  Google Scholar 

  33. Shavva, A.G., Vlasova, K.V., Tsogoeva, S.B., Egorov, M.S., and Yakutseni, P.P., Russ. J. Bioorg. Chem., 2002, vol. 28, no. 3, p. 209.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    S. N. Morozkina, I. A. Gluzdikov, A. S. Drozdov, S. I. Selivanov & A. G. Shavva

  2. Petersburg Nuclear Physics Institute, “Kurchatov Institute” National Research Center, Orlova Roshcha, Gatchina, Leningrad oblast, 188300, Russia

    R. A. Kovalev & M. V. Filatov

  3. Peter the Great St. Petersburg Polytechnic University, Politekhnicheskaya ul. 29, St. Petersburg, 195251, Russia

    M. V. Filatov

Authors
  1. S. N. Morozkina
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  2. I. A. Gluzdikov
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  3. A. S. Drozdov
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  4. S. I. Selivanov
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  5. R. A. Kovalev
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  6. M. V. Filatov
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  7. A. G. Shavva
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Correspondence to A. G. Shavva.

Additional information

Original Russian Text © S.N. Morozkina, I.A. Gluzdikov, A.S. Drozdov, S.I. Selivanov, R.A. Kovalev, M.V. Filatov, A.G. Shavva, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 3, pp. 425–430.

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Morozkina, S.N., Gluzdikov, I.A., Drozdov, A.S. et al. Synthesis and some biological properties of sulfamates derived from 8α-analogs of steroidal estrogens. Russ J Org Chem 51, 411–416 (2015). https://doi.org/10.1134/S1070428015030215

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  • DOI: https://doi.org/10.1134/S1070428015030215

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