ArticlePhotochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology2025
Photochemical access to flavone- and aurone-fused estrone derivatives.
Article in Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The fusion of privileged heterocyclic scaffolds with biologically relevant structures represents a powerful strategy for developing novel hybrid molecules with enhanced properties. In this work, we report the preparation of flavone- and aurone-fused estrone derivatives via a sequential photo-Fries rearrangement and intramolecular annulation approach. The photo-Fries reaction of estrone 3-phenylpropiolate ester efficiently afforded ortho-hydroxyaryl phenylethynyl ketones, which were further cyclized under basic conditions. The selective formation of flavone (6-endo-dig) or aurone (5-exo-dig) derivatives could be tuned by varying the base strength and solvent conditions. Moreover, the aurone-fused estrone compounds exhibited visible-light-responsive photoisomerization, opening new possibilities for their application as photoswitchable steroidal systems. This photochemical strategy offers a versatile and efficient method to access functionalized steroidal derivatives with potential in chemical biology and material sciences.
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