An expeditious one-pot synthesis of 1,6-dideoxy- N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-γ and IL-4

Abstract

An efficient ‘one-pot’ approach to the synthesis of 1,6-dideoxy- N-alkylated nojirimycin derivatives in good yields and with high stereoselectivity was developed. It was found that the synthetic N-alkylated iminosugars showed inhibitory effects on the release of the cytokines IFN-γ and IL-4 from the mouse splenocytes. The preliminary structure–activity relationship was deduced from the activities of N-substituted iminosugars. Apart from the cytokine inhibitory activities, a series of glycosidase inhibitory activities were also examined. The present experimental data demonstrated that synthetic iminosugars might hold potential as immunosuppressive agents.