L-Isofucoselenofagomine and derivatives: dual activities as antioxidants and as glycosidase inhibitors

Abstract

The synthesis of a series of l-fuco-configured selenosugars, isosters of the potent glycosidase inhibitor isofucofagomine has been accomplished by a double nucleophilic displacement of a dimesylated derivative with selenide anion generated in situ. Se-Alkylation and oxidation of the corresponding selenane afforded a selenonium and a selenoxide, respectively. The biological activities of such compounds have been evaluated, finding a dual activity caused by the presence of the selenium atom: the selenane exerted a good glutathione peroxidase mimicry by efficiently scavenging H2O2 in the presence of thiols, whereas the stable selenoxide derivative was found to be the first example of a selenosugar acting as a good α-l-fucosidase inhibitor.