A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies.
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.
Division of Organic Chemistry (Synthesis), National Chemical Laboratory Pune-411008, India. pandey@ems.ncl.res.in
Ganesh
G
Pandey
Manmohan
M
Kapur
M Islam
MI
Khan
Sushama M
SM
Gaikwad
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D006900:Hydroxylation; D050112:Imino Pyranoses; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D001372:Aza Compounds; D050112:Imino Pyranoses; D010880:Piperidines; C098432:isofagomine; D006026:Glycoside Hydrolases