An alternative route for tricyclic quinazolinone-iminosugars and their glucosidase inhibitory activities.

Autor: Li J; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Huang X; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Zhou L; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China; College of Chemistry and Chemical Engineering, Xingtai University, Xingtai, Hebei, 054001, China., Xie S; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Su L; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Wei C; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Li X; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China., Chen H; Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China. Electronic address: hua-todd@163.com.
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 2023 Dec; Vol. 534, pp. 108967. Date of Electronic Publication: 2023 Oct 11.
DOI: 10.1016/j.carres.2023.108967
Abstrakt: A series of novel tricyclic quinazolinone-iminosugars 5 and their derivatives 7 were obtained from the tosylated sugars by three steps. Firstly, the reaction of the isopropylidene protected sugar tosylate 1 and o-aminobenzylamine 2 generated the precursor tricyclic quinazolin-iminosuar 3, which was then oxidized by KMnO 4 to produce the corresponding quinazolinone 4. Finally, removal of the isopropylidene group yielded the target tricyclic quinazolinone iminosugars 5. In addition, quinazolinone-iminosugars 4ac, 4bc and 4cc who contain bromine in the aromatic region underwent Suzuki reaction with phenylboronic acid, followed with the removal of the isopropylidene group to afford the derivatives 7. This strategy will help to construct such fused multicyclic quinazolinone-iminosugars efficiently. Some compounds show certain inhibition against α-glucosidase (saccharomyce cerevisiae).
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2023 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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