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Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids.

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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Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids.

Pflug Nicholas C NC Knutson Christopher J CJ Martinović-Weigelt Dalma D Swenson Dale C DC Wammer Kristine H KH Cwiertny David M DM Gloer James B JB

Organic letters 20190425 10

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 paren ...[more]

PMID: 31021644

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