A series of iso--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 (IC = 9.3 μM) than the others. Molecular docking study revealed different docking modes of the iso--DNJ and L-isoDALDP derivatives from their parent compounds, and also the similarity of compound 30 to isofagomine.
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Design and synthesis of iso--DNJ and L-isoDALDP derivatives: pursuit of potent and selective inhibitors of α-glucosidase.
Org Biomol Chem
April 2023
Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
A series of iso--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 (IC = 9.3 μM) than the others.
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