New analogs of steroid estrogens |
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Authors: | S N Morozkina S K Nikol’skaya G L Starova S I Selivanov A G Shavva |
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Institution: | 1.St. Petersburg State University,St. Petersburg,Russia |
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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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