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