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New analogs of steroid estrogens

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Abstract

Aiming at the investigation of the mechanism of functioning of steroid estrogens a series of compounds with unnatural rings junction was synthesized. All investigated compounds exhibit a reduced uterotropic activity. It was established applying the NMR spectroscopy that 7α-methyl-3-methoxy-D-homo-6-oxa-8α,14β-estra-1,3,5(10)-trien-17a-one existed in solution in two conformations distinguished by the structure of the rings B, C, and D simultaneously. The reaction of 17-methylidene-3-methoxy-6-oxa-8α-estra-1,3,5(10)-triene with hydrobromic acid in acetic acid promotes a rearrangement with the migration of a methyl group into the position 17 resulting in the formation of 17,17-dimethyl-6-oxa-8α-gona-1,3,5(10),13(14)-tetraene derivatives.

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198504, Russia

    S. N. Morozkina, S. K. Nikol’skaya, G. L. Starova, S. I. Selivanov & A. G. Shavva

Authors
  1. S. N. Morozkina
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  2. S. K. Nikol’skaya
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  3. G. L. Starova
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  4. S. I. Selivanov
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  5. A. G. Shavva
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Correspondence to A. G. Shavva.

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Original Russian Text © S.N. Morozkina, S.K. Nikol’skaya, G.L. Starova, S.I. Selivanov, A.G. Shavva, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 8, pp. 1216–1221.

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Morozkina, S.N., Nikol’skaya, S.K., Starova, G.L. et al. New analogs of steroid estrogens. Russ J Org Chem 47, 1234–1239 (2011). https://doi.org/10.1134/S1070428011080203

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  • DOI: https://doi.org/10.1134/S1070428011080203

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