Model Studies on Peroxidic Glutathione Transferase (GST) Inhibitors: C5-Methylated 1,2,4-Trioxanes with C6-Acrylate Side Chains

Autor: Markus Pietsch, Axel G. Griesbeck, Maria Bräutigam, Andreas Maaßen
Rok vydání: 2015
Předmět:
Zdroj: European Journal of Organic Chemistry. 2015:4349-4352
ISSN: 1434-193X
DOI: 10.1002/ejoc.201500326
Popis: The 1,2-hydroxy hydroperoxide 7 was obtained with high threo diastereoselectivity from the ester-conjugated allylic alcohol 6 through a porphyrin-sensitized singlet oxygen ene reaction. Compound 7 was used as substrate for peroxy(trans)acetalization with aldehydes, orthoesters, and acetals, catalyzed by boron and indium Lewis acids, as well as by PPTS as a Bronsted acid catalyst (for trioxane 10). The 1,2,4-trioxane 8 was formed with high diasteroselectivity with all-equatorially positioned substitutents at C-3, C-5, and C-6. Additionally, perorthoester 9 was obtained by indium(III)-catalyzed condensation of an orthoester with the hydroperoxide 7. The new compounds 8 and 9 exhibited moderate inhibition of human placental glutathione transferase (GST), comparable to that shown by the 5-unsubstituted model trioxane 11.
Databáze: OpenAIRE
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