The synthesis and glycosidase inhibitory activity of analogues of tiruchanduramine

Zackary J.R. Ashworth, Barbara Bartholomew, Daniel M. Evans, Josephine Forde-Thomas, Karl F. Hoffmann, Reece Murdoch, Robert J. Nash, Hazel Sharp, Helen Whiteland, Patrick J. Murphy*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (SciVal)

Abstract

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.

Original languageEnglish
Pages (from-to)609-621
Number of pages13
JournalHeterocycles
Volume100
Issue number4
DOIs
Publication statusPublished - 19 Mar 2020

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