Synthesis and characterization of a fluorescent steroid dimer linked through C-19 by a 1,4-Bis(phenylethynyl)phenylene fragment

[Display omitted] •The synthesis of a fluorescent steroid dimer with androstanes cores is reported.•The cores are linked through C-19 by a 1,4 bis(phenylethynyl)benzene fragment.•The detailed NMR characterization is provided.•The UV and Fluorescence spectra were recorded.•The compound showed a quant...

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Bibliographic Details
Published in:Steroids 2022-11, Vol.187, p.109098-109098, Article 109098
Main Authors: Vazquez-Chavez, Josué, Aguilar-Granda, Andrés, Iglesias Arteaga, Martín A.
Format: Article
Language:English
Subjects:
1,4-Bis(phenylethynyl)phenylene bridge
Androstane
Fluorescent steroid dimer
NMR characterization
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Summary:[Display omitted] •The synthesis of a fluorescent steroid dimer with androstanes cores is reported.•The cores are linked through C-19 by a 1,4 bis(phenylethynyl)benzene fragment.•The detailed NMR characterization is provided.•The UV and Fluorescence spectra were recorded.•The compound showed a quantum yield of 60%. The synthesis and characterization of a dimer in which two nuclei of 3β-acetoxy-19-hydroxyandrost-5-en-17-one are linked by the fluorescent 1,4-bis(phenylethynyl)phenylene bridge attached to the oxygenated functions at positions C-19 of each steroid fragment is described. The compound was obtained in five steps and 23 % overall yield and showed a strong blue emission with a quantum yield of 0.66.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2022.109098