An alternative route for tricyclic quinazolinone-iminosugars and their glucosidase inhibitory activities.

A series of novel tricyclic quinazolinone-iminosugars 5 and their derivatives 7 were obtained from the tosylated sugars by three steps. Firstly, the reaction of the isopropylidene protected sugar tosylate 1 and o-aminobenzylamine 2 generated the precursor tricyclic quinazolin-iminosuar 3, which was then oxidized by KMnO4 to produce the corresponding quinazolinone 4. Finally, removal of the isopropylidene group yielded the target tricyclic quinazolinone iminosugars 5. In addition, quinazolinone-iminosugars 4ac, 4bc and 4cc who contain bromine in the aromatic region underwent Suzuki reaction with phenylboronic acid, followed with the removal of the isopropylidene group to afford the derivatives 7. This strategy will help to construct such fused multicyclic quinazolinone-iminosugars efficiently. Some compounds show certain inhibition against α-glucosidase (saccharomyce cerevisiae).