A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies |
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Authors: | Pandey Ganesh Kapur Manmohan Khan M Islam Gaikwad Sushama M |
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Affiliation: | Division of Organic Chemistry (Synthesis), National Chemical Laboratory Pune-411008, India. pandey@ems.ncl.res.in |
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Abstract: | A new synthetic strategy has been devised to access a variety of polyhydroxylated piperidines belonging to the azasugar class of glycosidase inhibitors. The key precursor (3aR, 7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro[1,3]dioxo[4,5-c]pyridine is obtained by photoinduced electron transfer (PET) cyclization of the corresponding alpha-trimethylsilylmethylamine radical cation to the tethered acetylene functionality. The new molecules have been evaluated for inhibitory properties for certain beta-glycosidases and have been found to be moderate to weak inhibitors of the enzymes under study. |
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