New α-galactosidase-inhibiting aminohydroxycyclopentanes??

RSC Advances Pub Date: 2021-04-29 DOI: 10.1039/D1RA02507D

Abstract

A set of cyclopentanoid α-galactosidase ligands was prepared from a partially protected ω-eno-aldose via a reliable (2 + 3)-cycloaddition protocol with slightly modified conditions. The obtained N-benzylisoxazolidine ring was selectively opened and the configuration of the hydroxymethylgroup was inverted. Consecutive deprotection provided an aminocyclopentane, which was N-alkylated to furnish a set of potential α-galactosidase inhibitors. Their glycosidase inhibitory activities were screened with a panel of standard glycosidases of biological significance.

Graphical abstract: New α-galactosidase-inhibiting aminohydroxycyclopentanes
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