Abstract
The stereochemical structure and conformational transformations of two 6-oxa-14β-estra-1,3,5(10), 8(9)-tetraenes having an α-methyl group at position 7 were investigated. It was found that the substituent at the C-17 atom has an effect on the formation of the conformers in solution. In the analog containing a C-17 keto group in solution there are two conformers, whereas the 17α-acetoxy derivative has only one conformer.
Similar content being viewed by others
References
J. Kalvoda, Ch. Krähnbühl, P. A. Desaulles, and G. Anner, Helv. Chim. Acta, 50, 281 (1967).
P. Wieland and G. Anner, Helv. Chim. Acta, 50, 289 (1967).
R. B. Gabbard and A. Segaloff, Steroids, 41, 791 (1983).
S. I. Selivanov, G. L. Starova, Sh. N. Abusalimov, and A. G. Shavva, Zh. Org. Khim., 42, 215 (2006).
G. M. Anstead, K. E. Carlson, and J. A. Katzenellenbogen, Steroids, 62, 268 (1997).
O. Jänne, K. Kontula, R. Vihko, P. Pystynen, O. Auvinen, and K. Lauslahti, Med. Biol., 53, 214 (1975).
W. Römer, M. Oettel, P. Droescher, and S. Schwarz, Steroids, 62, 304 (1997).
O. Dann, K.-W. Hagedorn, and H. Hofmann, Chem. Ber., 104, 3313 (1971).
D. Neuhaus and M. P. Williamson, The Nuclear Overhauser Effect in Structural and Conformational Analysis, 2nd. Ed., VCH, New York (2000).
S. I. Selivanov and A. G. Shavva, Rus. J. Bioorg. Chem., 28, 194 (2002).
U. Piantini, O. W. Sorensen, and R. R. Ernst, J. Am. Chem. Soc., 104, 6800 (1982).
M. Rance, O. W. Sorensen, G. Bodenhausen, C. Wagner, and R. R. Ernst, Biochem. Biophys. Res. Commun., 117, 479 (1983).
W. P. Aue, J. Karhan, and R. R. Ernst, J. Chem. Phys., 64, 4226 (1976).
D. D. Traficante and M. D. Meadows, Concepts Magn. Reson., 9, 359 (1997).
J. Jeener, G. H. Meier, P. Bachman, and R. R. Ernst, J. Chem. Phys., 71, 4546 (1979).
N. H. Andersen, H. L. Eaton, and X. Lai, Magn. Reson. Chem., 27, 515 (1989).
M. K:ock and C. Griesinger, Angew. Chem., Int. Ed. Engl., 33, 332 (1994).
A. G. Shavva, G. L. Starova, S. I. Selivanov, and S. N. Morozkina, Khim. Geterotsikl. Soedin., 202 (2008). [Chem. Heterocycl. Comp., 44, 148 (208)].
S. I. Selivanov, A. Yu. Solovyev, S. N. Morozkina, and A. G. Shavva, in: XVIII Mendeleev Congress on General and Applied Chemistry, Moscow, September 23–28 (2007). Abstr. Book, 2105.
J. Keeler, D. Neuhaus, and M. P. Williamson, J. Magn. Res., 73, 45 (1987).
Sh. N. Abusalimov, S. K. Nikol'skaya, G. L. Starova, S. I. Selivanov, and A. G. Shavva, Zh. Org. Khim., 42, 50 (2006).
I. A. Gluzdikov, M. S. Egorov, S. I. Selivanov, G. L. Starova, and A. G. Shavva, Zh. Org. Khim., 42, 1687 (2006).
Author information
Authors and Affiliations
Corresponding author
Additional information
In memory of Prof. A. A. Potekhin.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 82–834, June, 2008.
Rights and permissions
About this article
Cite this article
Selivanov, S.I., Morozkina, S.N., Chentsova, A.S. et al. Investigation of the conformational transformations in some 7α-methyl-6-oxa-14β-analogs of steroidal estrogens by NMR spectroscopy. Chem Heterocycl Comp 44, 654–665 (2008). https://doi.org/10.1007/s10593-008-0091-8
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0091-8