The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

Five analogues (7a-e) of the metabolite tiruchanduramine 1 were prepared. Compounds 7d and 7e were specific inhibitors of yeast α-glucosidase, whilst 7e specifically inhibited Bacillus α-glucosidase. Compounds 7b and 7c were the best inhibitors of β-glucosidase. All 5 compounds inhibited β-galactosidase, but once again 7e was the best inhibitor. It was apparent that different chain lengths in the compounds 7a-e affect the degree of inhibition. Some of the synthetic analogues show significantly improved inhibition of α-glucosidases when compared to tiruchanduramine 1 and also improved specificity.