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Molecular structures of some 8-isoanalogues of steroid estrogens

  • Structure of Organic Compounds
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Abstract

The molecular structures of three steroids, namely, 17β-acetoxy-3-methoxy-8-isoestra-1,3,5(10)-triene (I), 17β-acetoxy-3-methoxy-7α-methyl-8-isoestra-1,3,5(10)-triene (II), and 17β-acetoxy-3-methoxy-1-methyl-8-isoestra-1,3,5(10)-triene (III), are determined by X-ray diffraction analysis. It is shown that the substituents in the A and B rings of the compounds of the 8-iso series have a slight effect on the conformation of the steroid skeleton as a whole, which manifests itself only in insignificant distortions of the B and D rings. The methyl group in the 1-position (compound III) affects the geometric parameters of the steroid nucleus less than the same substituent in the 7-position (compound II). A sharp decrease in the uterotropic activity of compounds II and III (compared to compound I) revealed in biological studies can be attributed to unfavorable steric interactions of the substituents in the A and B rings with the estradiol receptor.

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References

  1. E. von Angerer, The Estrogen Receptor as a Target for Rational Drug Design (Springer-Verlag, New York, 1996).

    Google Scholar 

  2. J. E. Compston, Clin. Endocrinol. (Oxf) 48, 389 (1998).

    Article  Google Scholar 

  3. F. B. González, G. Neef, U. Eder, et al., Steroids 40(2), 171 (1982).

    Google Scholar 

  4. I. V. Torgov, Bioorgan. Khim. 10(8), 1059 (1984).

    Google Scholar 

  5. L. G. Acselrud, Yu. N. Griun, P. Yu. Zavalii, et al., in Collected Abstracts of XII European Crystallography Meeting, Moscow, 1989 (Nauka, Moscow, 1989), Vol. 3, p. 155.

    Google Scholar 

  6. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 49, S53 (1993).

    Google Scholar 

  7. I. L. Shamovskii, G. M. Barenboim, and A. A. Ovchinnikov, Bioorgan. Khim. 9(8), 1113 (1983).

    Google Scholar 

  8. E. Palomino, M. J. Heeg, J. P. Horwitz, et al., J. Steroid Biochem. 35(2), 219 (1990).

    Article  Google Scholar 

  9. F. Kayser, D. Maes, L. Wyns, et al., Steroids 60, 713 (1995).

    Article  Google Scholar 

  10. M. Kh. Dzhafarov, M. V. Dodonov, S. N. Ananchenko, et al., Bioorgan. Khim. 12(7), 970 (1986).

    Google Scholar 

  11. H. P. Weber and E. Galantay, Helv. Chim. Acta 55(57), Fasc. 2, 544 (1972).

    Google Scholar 

  12. B. Busetta and M. Hospital, Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 43, 1206 (1972).

    Google Scholar 

  13. G. M. Anstead, K. E. Carlson, and J. A. Katzenellenbogen, Steroids 62(3), 268 (1997).

    Article  Google Scholar 

  14. M. A. Dzhafarov, M. V. Dodonov, S. N. Ananchenko, et al., Bioorgan. Khim. 12(7), 981 (1986).

    Google Scholar 

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Authors and Affiliations

  1. St. Petersburg State University (Petrodvorets Branch), Universitetskii pr. 2, Petrodvorets, 198904, Russia

    G. L. Starova, I. I. Eliseev, Sh. N. Abusalimov, S. B. Tsogoeva & A. G. Shavva

Authors
  1. G. L. Starova
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  2. I. I. Eliseev
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  3. Sh. N. Abusalimov
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  4. S. B. Tsogoeva
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  5. A. G. Shavva
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Translated from Kristallografiya, Vol. 46, No. 1, 2001, pp. 72–75.

Original Russian Text Copyright © 2001 by Starova, Eliseev, Abusalimov, Tsogoeva, Shavva.

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Starova, G.L., Eliseev, I.I., Abusalimov, S.N. et al. Molecular structures of some 8-isoanalogues of steroid estrogens. Crystallogr. Rep. 46, 65–68 (2001). https://doi.org/10.1134/1.1343129

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  • DOI: https://doi.org/10.1134/1.1343129

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