Synthesis and biological activity of some 8α-analogs of steroidal estrogens

8α-Analogs of steroidal estrogens containing a methyl group on C 1 or an oxo group on C 6 were synthesized with a view to obtain compounds exhibiting selective biological activity, and their steric structure was studied. As shown with 1,3- O -dimethyl-8α-estrone as an example, such compounds in solu...

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 49; no. 4; pp. 603 - 609
Main Authors Morozkina, S. N., Abusalimov, Sh. N., Selivanov, S. I., Shavva, A. G.
Format Journal Article
LanguageEnglish
Published Dordrecht SP MAIK Nauka/Interperiodica 01.04.2013
Springer Nature
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Organic Chemistry
Physical Sciences
Science & Technology
Spectral Matrix
Sodium Dichromate
Steroidal Estrogen
Hypocholesterolemic Activity
Raney Nickel
CARCINOGENESIS
SPECTROSCOPY
HORMONE-REPLACEMENT THERAPY
RISK
IDENTIFICATION
CANCER
MILLION WOMEN
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Summary:8α-Analogs of steroidal estrogens containing a methyl group on C 1 or an oxo group on C 6 were synthesized with a view to obtain compounds exhibiting selective biological activity, and their steric structure was studied. As shown with 1,3- O -dimethyl-8α-estrone as an example, such compounds in solution can exist as two conformers, whereas the oxo group on C 6 almost does not affect conformation of the modified derivative as compared to the parent structure. Some newly synthesized compounds exhibited hypocholesterolemic activity in combination with reduced uterotropic effect, which is important for the design of drugs for the treatment of atherosclerosis. 6-Oxo-8α-analogs showed osteoprotective activity, so that introduction of an oxo group into the 6-position is promising from the viewpoint of hormone replacement therapy.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428013040180