Novel 2-aryl-3,4,5-trihydroxypiperidines: Synthesis and glycosidase inhibition

Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines (6–8 and their enantiomers), the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six-membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition (IC50 1080 μmol/L) against β-galactosidase from rat intestinal lactases.

Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines (6–8 and their enantiomers), the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from six-membered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection.Figure optionsDownload as PowerPoint slide