Jump to main content
Jump to site search

Issue 34, 2018
Previous Article Next Article

Divergent synthesis of new α-glucosidase inhibitors obtained through a vinyl Grignard-mediated carbocyclisation

Author affiliations

Abstract

Four new α-glucosidase inhibitors have been synthesised through 5–8 synthetic steps from a common synthetic intermediate obtained through a recently developed carbocyclisation. The compounds were designed as hybrids of the known glucosidase inhibitors valienamine, voglibose and miglitol. All four compounds showed activity against rat intestinal sucrase with the most potent inhibitor acting at low micromolar concentration. The newly synthesised compounds were not as potent as miglitol against sucrase but showed greater selectivity towards the tested glycosidases. The most potent inhibitors were docked into a homology model built for this study of rat intestinal sucrase explaining the difference in potency between two diastereoisomers with varying orientation of a secondary amine.

Graphical abstract: Divergent synthesis of new α-glucosidase inhibitors obtained through a vinyl Grignard-mediated carbocyclisation

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Jun 2018, accepted on 06 Aug 2018 and first published on 07 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01433G
Citation: Org. Biomol. Chem., 2018,16, 6250-6261
  •   Request permissions

    Divergent synthesis of new α-glucosidase inhibitors obtained through a vinyl Grignard-mediated carbocyclisation

    I. M. B. Knudsen, C. Hedberg, L. K. Ladefoged, D. Ide, A. Brinkø, E. Z. Eikeland, A. Kato and H. H. Jensen, Org. Biomol. Chem., 2018, 16, 6250
    DOI: 10.1039/C8OB01433G

Search articles by author

Spotlight

Advertisements