Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

• Davide Bini,
• Francesca Cardona,
• Matilde Forcella,
• Camilla Parmeggiani,
• Paolo Parenti,
• Francesco Nicotra and
• Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

• 10.3762/bjoc.8.58 Abstract A small set of nojirimycin- and pyrrolidine-based iminosugar derivatives has been synthesized and evaluated as potential inhibitors of porcine and insect trehalases. Compounds 12, 13 and 20 proved to be active against both insect and porcine trehalases with selectivity towards

• scarcely characterised. Keywords: glycosidases inhibitors; iminosugars; nojirimycins; pyrrolidines; trehalases; Introduction Trehalase (EC3.2.1.28) is a glycosidase that catalyses trehalose (α-D-glucopyranosyl-α-D-glucopyranoside 1, Figure 1) [1][2][3] hydrolysis. It was found initially at the end of the

• amounts of the benzyl urea that could not be fully hydrolysed, even after prolonged reaction times. In order to figure out whether the benzyl urea moiety might have any effect on the activity and specificity against trehalases, derivative 13 was also synthesized by direct hydrogenolysis of starting