Flexible synthesis and biological evaluation of novel 5-deoxyadenophorine analogues

Adenophorine and its 5-deoxy analogue have been identified as natural iminosugars with efficient glycosidase inhibitory effects. The syntheses and biological evaluation of two new series of 5-deoxyadenophorine analogues in their racemic form are reported. The compounds 12e and 13d bearing a C11 and C7 alkyl chain, respectively, were found to be potent inhibitors of the β-glucosidase from almond with Ki near to 60 μM. The compounds 13a,d which possess a 3,4-cis stereochemistry were efficient on glucosidases but also on the β-galactosidase, what was not observed with the 3,4-trans series 12.

Graphical abstractTwo series of novel analogues of 5-deoxyadenophorine with lipophilic side-chains (C2–C11) are prepared and tested on a range of glycosidases.Figure optionsDownload full-size imageDownload as PowerPoint slide