Probing the Influence of Linker Length and Flexibility in the Design and Synthesis of New Trehalase Inhibitors.

ABSTRACT: This work aims to synthesize new trehalase inhibitors selective towards the insect trehalase versus the porcine trehalase, in view of their application as potentially non-toxic insecticides and fungicides. The synthesis of a new pseudodisaccharide mimetic 8, by means of a stereoselective α-glucosylation of the key pyrrolizidine intermediate 13, was accomplished. The activity of compound 8 as trehalase inhibitor towards C.riparius trehalase was evaluated and the results showed that 8 was active in the μM range and showed a good selectivity towards the insect trehalase. To reduce the overall number of synthetic steps, simpler and more flexible disaccharide mimetics 9-11 bearing a pyrrolidine nucleus instead of the pyrrolizidine core were synthesized. The biological data showed the key role o

SUBMITTER: D'Adamio G 

PROVIDER: S-EPMC6017881 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature