Abstract
By X-ray crystallographic analysis and NMR spectroscopy it was demonstrated that the conformations of several D-homo-6-oxa-8α analogs of steroidal estrogens are similar in the crystal and in solution. The distances between the hydrogen atoms in these molecules, calculated by the ab initio and MM+ methods, correspond to the experimental data.
Similar content being viewed by others
References
G. S. Chetrite and J. R. Pasqualini, J. Steroid Biochem. Mol. Biol., 76, 95 (2001).
D. A. Holt, H.-J. Oh, M. A. Levy, and B. W. Metcalf, Steroids, 56, 4 (1991).
P.-K. Li, R. Pillai, and L. Dibbelt, Steroids, 60, 299 (1995).
A. Purohit, H. A. M. Hejaz, L. W. L. Woo, A. E. van Strien, B. V. L. Potter, and M. J. Reed, J. Steroid Biochem. Mol. Biol., 69, 227 (1999).
D. S. Fischer, G. M. Allan, C. Bubert, N. Vicker, A. Smith, H. J. Tutill, A. Purohit, L. Wood, G. Packham, M. F. Mahon, M. J. Reed, and B. V. L. Potter, J. Med. Chem., 48, 5749 (2005).
H. R. Lawrence, N. Vicker, G. M. Allan, A. Smith, M. F. Mahon, H. J. Tutill, A. Purohit, M. J. Reed, and B. V. L. Potter, J. Med. Chem., 48, 2759 (2005).
M. Numazawa, M. Ando, Y. Watari, T. Tominaga, Y. Hayata, and A. Yoshimura, J. Steroid Biochem. Mol. Biol., 96, 51 (2005).
C. Wang, M. Zhao, J. Yang, and S. Peng, Steroids, 66, 811 (2001).
C. Wang, W. Cui, M. Zhao, J. Yang, and S. Peng, Bioorg. Med. Chem. Letters, 13, 143 (2003).
C. Wang, M. Zhao, X. Qiu, and S. Peng, Bioorg. Med. Chem., 12, 4403 (2004).
S. N. Morozkina, A. G. Shavva, Screening and MedChemEurope. 20–21 February 2007, Palau De Congressor De Catalunia, Barcelona, Spain, Presentation.
A. G. Shavva, S. N. Morozkina, I. V. Ishchenko, I. I. Eliseev, S. I. Selivanov, Sh. N. Abusalimov, S. S. Selivanov, I. Yu. Kameneva, and N. D. Eshchenko, Bioorgan. Khim., 33, 310 (2007).
G. M. Anstead, K. E. Carlson, and J. A. Katzenellenbogen, Steroids, 62, 268 (1997).
S. C. Brooks and D. F. Skafar, Steroids, 69, 401 (2004).
A. K. Shiau, D. Barstad, P. M. Loria, L. Cheng, P. J. Kushner, D. A. Agard, and G. L. Green, Cell, 95, 927 (1998).
J. M. Blaney and J. S. Dixon, Perspect. Drug Discovery Design., 1, 301 (1993).
P. M. Colman, Curr. Opin. Struct. Biol, 4, 868 (1994).
I. D. Kuntz, Science, 257, 1078 (1992).
T. Lengauer and M. Rarey, Curr. Opin. Struct. Biol., 6, 402 (1996).
T. P. Lybrand, Curr. Opin. Struct. Biol., 5, 224 (1995).
F. Kayser, D. Maes, L. Wyns, J. Lisgarten, R. Palmer, D. Lisgarten, R. Willem, J. C. Martins, P. Verheyden, and M. Biesemans, Steroids, 60, 713 (1995).
B. Schönecker, C. Lange, M. Kötteritzsch, W. Günter, J. Weston, E. Anders, H. Görls, J. Org. Chem., 65, 5487 (2000).
F. Commodari, G. Sclavos, S. Ibrahimi, A. Khiat, and Y. Boulanger, Magn. Res. Chem., 43, 444 (2005).
V. N. Belov, V. Yu. Dudkin, E. A. Urusova, G. L. Starova, S. I. Selivanov, S. V. Nikolaev, N. D. Eshchenko, S. N. Morozkina, and A. G. Shavva, Biorgan. Khim., 33, 315 (2007).
G. L. Starova, S. S. Selivanov, M. S. Egorov, S. I. Selivanov, and A. G. Shavva, Kristallografiya, 49, 502 (2004).
G. L. Starova, K. V. Vlasova, Sh. N. Abusalimov, and A. G. Shavva, [in Russian], in: Abstracts RSNE-2003, Moscow (2003), p. 94.
G. M. Sheldrick, SHELXL97, Univ. of Göttingen, Germany (1997).
A. G. Shavva, K. V. Vlasova, S. B. Tsogoeva, M. S. Egorov, and P. P. Yakutseni, 28, 236 (2002).
A. M. Brzozowski, A. C. Pike, Z. Dauter, R. E. Hubbard, T. Bonn, O. Engström, L. Öhman, G. L. Green, J.-Å. Gustafsson, and M. Garlquist, Nature, 389, 753 (1997).
C. L. Deal, and M. W. Drapper, Women’s Health, 2, 199 (2006).
J. M. Faupel-Badger, S. A. Prindiville, D. Venzon, B. K. Vonderhaar, Jo A. Zujewski, and J. Eng-Wong, J. Cancer Epidemiology, Biomarkers and Prevention, 15, 1153 (2006).
Author information
Authors and Affiliations
Corresponding author
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 202–207, February, 2008.
Rights and permissions
About this article
Cite this article
Shavva, A.G., Starova, G.L., Selivanov, S.I. et al. Molecular structures of some D-homo-6-oxa-8α analogs of steroidal estrogens. Chem Heterocycl Comp 44, 148–152 (2008). https://doi.org/10.1007/s10593-008-0036-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0036-2