Polyhydroxylated pyrrolidine and 2-oxapyrrolizidine as glycosidase inhibitors
Journal
MedChemComm
Journal Volume
4
Journal Issue
5
Pages
783-791
Date Issued
2013
Author(s)
Abstract
Using D-serine as a chiral precursor, a polyhydroxylated pyrrolidine (1), its derivatives bearing carboxylate, phosphate and phosphonate groups (2-4) and an oxapyrrolizidine (5) were synthesized. The pyrrolidine ring was formed by intramolecular amino-mercuration. The bicyclic scaffold of oxapyrrolizidine was further constructed by an intramolecular attack of the carbamate group on the iodomethyl group. Compounds 1 and 5 were found to inhibit β-glucosidase and α-galactosidase, respectively, in a competitive manner, whereas compounds 2, 3 and 4 did not produce significant inhibition against glycosidases. © The Royal Society of Chemistry 2013.
SDGs
Type
journal article