Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

Abstract

The synthesis of new multivalent architectures based on a trihydroxypiperidine α-fucosidase inhibitor is reported herein. Tetravalent and nonavalent dendrimers were obtained by means of the click chemistry approach involving the copper azide-alkyne-catalyzed cycloaddition (CuAAC) between suitable scaffolds bearing terminal alkyne moieties and an azido-functionalized piperidine as the bioactive moiety. A preliminary biological investigation is also reported towards commercially available and human glycosidases.

Keywords

• dendrimers
• glycosidase inhibitors
• iminosugars
• multivalency
• piperidine alkaloids