Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids.
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ABSTRACT: In an ongoing effort to study the environmental fate of endocrine-active steroid hormones, we report the formation of phenolic rearrangement products (3 and 4) with a novel 6,5,8,5-ring system following aqueous photolysis of dienogest (1) and methyldienolone (2). The structures were established by analysis of 2D NMR and HRMS data, and that of 3 was confirmed by X-ray diffraction analysis. These photoproducts exhibit progestogenic and androgenic activity, albeit with less potency than their parent compounds.
SUBMITTER: Pflug NC
PROVIDER: S-EPMC7059344 | biostudies-literature | 2019 May
REPOSITORIES: biostudies-literature
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