Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors

Maria Domingues (1) , Justyna Jaszczyk (1) , Maria Isabel Ismael (2) , José Albertino Figueiredo (2) , Richard Daniellou (1) , Pierre Lafite (1) , Marie Schuler (1) , Arnaud Tatibouët (1)

1 ICOA - Institut de Chimie Organique et Analytique
2 UBI - University of Beira Interior [Portugal]

The synthesis of fused bicyclic oxazolidin-2-one (OZO) iminosugars was achieved through a tandem Staudinger reduction/retro-Michael/intramolecular Michael addition from the corresponding OZO azidosugars. Those precursors, based on both aldopentofuranoses and ketofuranohexoses backbones, were obtained following alkylation and oxidation of the related oxazolidine-2-thione (OZT) azidosugars. Eight OZO based iminosugars were isolated in good yields and evaluated for their potency as glycosidases inhibitors, thus extending the family of known 1-Deoxynojirimycin (DNJ) bicyclic analogues.

Domaines: Chimie; Chimie organique

Maria Domingues, Justyna Jaszczyk, Maria Isabel Ismael, José Albertino Figueiredo, Richard Daniellou, et al.. Conformationally restricted oxazolidin‐2‐one fused bicyclic iminosugars as potential glycosidase inhibitors. European Journal of Organic Chemistry, 2020, 2020 (38), pp.6109-6126. ⟨10.1002/ejoc.202001053⟩. ⟨hal-03478285⟩