Journal article
Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids
Organic letters, Vol.21(10), pp.3568-3571
05/17/2019
DOI: 10.1021/acs.orglett.9b00972
PMCID: PMC7059344
PMID: 31021644
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.
Details
- Title: Subtitle
- Bioactive Rearrangement Products from Aqueous Photolysis of Pharmaceutical Steroids
- Creators
- Nicholas C PflugChristopher J KnutsonDalma Martinović-WeigeltDale C SwensonKristine H WammerDavid M CwiertnyJames B Gloer
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.21(10), pp.3568-3571
- DOI
- 10.1021/acs.orglett.9b00972
- PMID
- 31021644
- PMCID
- PMC7059344
- NLM abbreviation
- Org Lett
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Publisher
- United States
- Grant note
- P30 ES005605 / NIEHS NIH HHS
- Language
- English
- Date published
- 05/17/2019
- Academic Unit
- Center for Health Effects of Environmental Contamination; Civil and Environmental Engineering; IIHR--Hydroscience and Engineering; Public Policy Center (Archive); Chemistry; Chemical and Biochemical Engineering
- Record Identifier
- 9983985706802771
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