Journal article
Intramolecular [2 + 2] Photocycloaddition of Altrenogest: Confirmation of Product Structure, Theoretical Mechanistic Insight, and Bioactivity Assessment
Journal of organic chemistry, Vol.84(17), pp.11366-11371
09/06/2019
DOI: 10.1021/acs.joc.9b02070
PMID: 31381858
Abstract
While studying the environmental fate of potent endocrine-active steroid hormones, we observed the formation of an intramolecular [2 + 2] photocycloaddition product (2) with a novel hexacyclic ring system following the photolysis of altrenogest (1). The structure and absolute configuration were established by X-ray diffraction analysis. Theoretical computations identified a barrierless two-step cyclization mechanism for the formation of 2 upon photoexcitation. 2 exhibited progesterone, estrogen, androgen, and pregnane X receptor activity, albeit generally with reduced potency relative to 1.
Details
- Title: Subtitle
- Intramolecular [2 + 2] Photocycloaddition of Altrenogest: Confirmation of Product Structure, Theoretical Mechanistic Insight, and Bioactivity Assessment
- Creators
- Nicholas C Pflug - ETH ZurichEric V Patterson - Stony Brook UniversityDalma Martinović-Weigelt - Department of BiologyEdward P Kolodziej - University of WashingtonJames B Gloer - University of IowaKristopher McNeill - ETH ZurichDavid M Cwiertny - University of IowaKristine H Wammer - University of St. Thomas (Minnesota)
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.84(17), pp.11366-11371
- DOI
- 10.1021/acs.joc.9b02070
- PMID
- 31381858
- NLM abbreviation
- J Org Chem
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Publisher
- American Chemical Society
- Grant note
- DOI: 10.13039/501100003006, name: Eidgen?ssische Technische Hochschule Z?rich; DOI: 10.13039/100000001, name: National Science Foundation, award: CHE-1229354, CHE-1609669, CHE-1609791, CHE-1662030, CHE-1335711, CBET-1336165
- Language
- English
- Date published
- 09/06/2019
- Academic Unit
- Center for Health Effects of Environmental Contamination; Civil and Environmental Engineering; Public Policy Center (Archive); Chemistry; Chemical and Biochemical Engineering
- Record Identifier
- 9984196972802771
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