Design and synthesis of iso-allo-DNJ and L-isoDALDP derivatives: pursuit of potent and selective inhibitors of α-glucosidase

Lin-Feng Yang, Ming Zhang, Yuna Shimadate, Atsushi Kato, Tian-Yang Liu Hou, Yi-Xian Li, Yue-Mei Jia, George W J Fleet, Chu-Yi Yu

研究成果: ジャーナルへの寄稿学術論文査読

1 被引用数 (Scopus)

抄録

A series of iso-allo-DNJ and L-isoDALDP derivatives were synthesized from dithioacetal 16 with sequential and highly diastereoselective Ho and Henry reactions, and aziridinium intermediate-mediated ring rearrangement as key steps. Glycosidase inhibition assay found four of them as selective α-glucosidase inhibitors, and the less substituted compound 30 showed more potent α-glucosidase inhibition (IC50 = 9.3 μM) than the others. Molecular docking study revealed different docking modes of the iso-allo-DNJ and L-isoDALDP derivatives from their parent compounds, and also the similarity of compound 30 to isofagomine.

本文言語英語
ページ(範囲)3453-3464
ページ数12
ジャーナルOrganic and Biomolecular Chemistry
21
16
DOI
出版ステータス出版済み - 2023/04/26

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