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Title: Intramolecular [2 + 2] Photocycloaddition of Altrenogest: Confirmation of Product Structure, Theoretical Mechanistic Insight, and Bioactivity Assessment.

Authors: Pflug, Nicholas C; Patterson, Eric V; Martinović-Weigelt, Dalma; Kolodziej, Edward P; Gloer, James B; McNeill, Kristopher; Cwiertny, David M; Wammer, Kristine H

Published In J Org Chem, (2019 09 06)

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.

PubMed ID: 31381858 Exiting the NIEHS site

MeSH Terms: Cycloaddition Reaction; Density Functional Theory; Humans; Photochemical Processes*; Receptors, Cytoplasmic and Nuclear/metabolism; Trenbolone Acetate/analogs & derivatives*; Trenbolone Acetate/chemical synthesis; Trenbolone Acetate/chemistry; Trenbolone Acetate/metabolism

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