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

• Main Authors: Davide Bini, Francesca Cardona, Matilde Forcella, Camilla Parmeggiani, Paolo Parenti, Francesco Nicotra, Laura Cipolla
• Format: Article
• Language: English
• Published: Beilstein-Institut 2012-04-01
• Series: Beilstein Journal of Organic Chemistry
• Subjects: glycosidases inhibitors; iminosugars; nojirimycins; pyrrolidines; trehalases
• Online Access: https://doi.org/10.3762/bjoc.8.58
• ISSN: 1860-5397

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 the insect glycosidase, while compounds 10, 14 and 16 behaved as inhibitors only of insect trehalase. Despite the fact that the activity was found in the micromolar range, these findings may help in elucidating the structural features of this class of enzymes of different origin, which are still scarcely characterised.