Title
Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids
Department/School
Chemistry
Date
5-17-2019
Document Type
Article
Keywords
Molecular structure, nandrolone analogs and derivatives, nandrolone chemistry, pharmaceutical preparations, photolysis, steriods chemistry
DOI
https://doi.org/10.1021/acs.orglett.9b00972
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.
Published in
Organic Letters
Citation/Other Information
Pflug, N.C., C.J. Knutson, D. Martinovic-Weigelt, D.C. Swenson, K.H. Wammer, D.M. Cwiertny, J.B. Gloer. 2019. "Bioactive rearrangement products from aqueous photolysis of pharmaceutical steroids." Organic Letters, 21:3658-3571. DOI: 10.1021/acs.orglett.9b00972