Skip to main content
Log in

Cytotoxic steroids with antiestrogenic activity of the 11α-acyloxyestra-1,3,5(10)-triene series

  • Letters to the Editor
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

Esterification of 3-hydroxyl group in 11α-acyloxyestra-1,3,5(10)-trienes with p-[bis(2-chloroethyl)amino]phenyl acetic acid led to antitumor steroids displaying antiestrogenic and cytotoxic activities. Our substances exhibit their activities on the model of murine mammary adenocarcinoma Ca-755, with inhibition of the tumor growth being 94–99%. A new approach was used to the 11α-hydroxylation of estra-1,3,5(10)-trienes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Abbreviations

DDQ:

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

DMAP:

4-dimethylaminopyridine

TEA:

triethylamine

References

  1. Sof’ina, Z.P. and Lagova, N.D., Sov. Med. Rev. Oncol., 1992, vol. 4, pp. 1–55.

    Google Scholar 

  2. Belousova, A.K. and Suslova, O.A., Ross. Onkol. Zh., 1997, no. 2, p. 49.

  3. Suzuki, Y.H., Taga, H., and Ishizuki, K., Ann. N. Y. Acad. Sci., 1983, vol. 417, pp. 234–239.

    Google Scholar 

  4. Preobrazhenskaya, M.N., Zh. Vses. Khim. O-va im. D. I. Mendeleeva, 1986, vol. 31, pp. 332–341.

    CAS  Google Scholar 

  5. Johanson, J.E., Anderson, S.O., Becham, K.W., and Zabor, G., J. Clin. Oncol., 1988, vol. 11,Suppl. 2, pp. 183–186.

    Google Scholar 

  6. Cytotoxic Estrogens in Hormone Receptive Tumors, Raus, J., Martens, H., and Leclercq, G., Eds., London: Academic, 1980.

    Google Scholar 

  7. Gilbert, J., Fuentes, M., Ojasoo, T., Dore, J., and Pons, M., J. Med. Chem., 1997, vol. 40, pp. 1104–1111.

    Article  PubMed  CAS  Google Scholar 

  8. Ferland, L., Labric, F., Kelly, P.A., and Raynaud, J.P., Biol. Reprod., 1978, vol. 18, pp. 99–104.

    Article  PubMed  CAS  Google Scholar 

  9. Collins, D.Y. and Sjovall, Y., Aust. J. Chem., 1983, vol. 36, pp. 339–360.

    CAS  Google Scholar 

  10. Golubovskaya, L.E., Minailova, O.N., Rzheznikov, V.M., and Tolkachev, V.N., Abstracts of Papers, II Int. Symposium on the Chemistry of Natural Comp., Eskisehir, Turkey, 1996, p. 138.

  11. Sykes, P.J., Rutherford, F.G., Laing, S.B., Phillips, J.H., and Turnbull, J.P., Tetrahedron Lett., 1971, pp. 3393–3396.

  12. Rzheznikov, V.M., USSR Inventor’s Certificate No. 1 395 639, Byull. Izobret., 1988, no. 18.

  13. Rzheznikov, V.M., Zh. Org. Khim., 1989, vol. 25, pp. 1568–1570.

    CAS  Google Scholar 

  14. Wu, Y. and Blackwell, L.F., Steroids, 1993, vol. 58, pp. 452–456.

    PubMed  CAS  Google Scholar 

  15. Kuhajda, K., Kandrac, J., Cirin-Novta, V., and Milkovic, D., Collect. Czech. Chem. Commun., 1996, vol. 61, pp. 1073–1076.

    Article  CAS  Google Scholar 

  16. Garin, A.M., in Novye tsitostatiki v lechenii zlokachestvennykh opukholei (New Cytostatics in Treatment of Malignant Tumors), Gorbunova, V.A., Ed., Moscow: Meditsina, 1998, pp. 41–60.

    Google Scholar 

  17. Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley and Sons, 1968. Translated under the title Reagenty dlya organicheskogo sinteza, Moscow: Mir, 1970, vol. 1, p. 422.

    Google Scholar 

  18. Rukovodstvo po eksperimental’nomu (doklinicheskomu) izucheniyu novykh farmakologicheskikh veshchestv [Handbook on Experimental (Preclinical) Study of New Pharmacological Substances], Moscow: Remedium, 2000, pp. 319–325.

  19. Michina, H., Schneider, M.R., Nishino, Y., and El Etreby, M.F., J. Steroid Biochem., 1989, vol. 34, pp. 447–453.

    Google Scholar 

  20. Bowler, J., Lilley, T.J., Pittam, J.D., and Wakeling, A.E., Steroids, 1989, vol. 54, pp. 71–100.

    Article  PubMed  CAS  Google Scholar 

  21. Schneider, M.R., and Angerer, E., J. Med. Chem., 1982, vol. 25, p. 1070.

    PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. M. Rzheznikov.

Additional information

Original Russian Text © L.E. Golubovskaya, Z.S. Smirnova, V.N. Tolkachev, V.M. Rzheznikov, 2006, published in Bioorganicheskaya Khimiya, 2006, Vol. 32, No. 2, pp. 221–224.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Golubovskaya, L.E., Smirnova, Z.S., Tolkachev, V.N. et al. Cytotoxic steroids with antiestrogenic activity of the 11α-acyloxyestra-1,3,5(10)-triene series. Russ J Bioorg Chem 32, 201–203 (2006). https://doi.org/10.1134/S1068162006020130

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162006020130

Key words

Navigation