Synthesis of substituted chiral piperazones resembling aza-sugars.
(6R)-6-(Hydroxymethyl)piperazin-2-one (1), (6S)-6-(hydroxymethyl)piperazin-2-one (2) and (6S)-6-[(1R, 2S, 3R)-1,2,3,4-tetrahydroxybutyl]piperazin-2-one (3) have been prepared in optically pure forms starting from D-glucosamine hydrochloride (4). The compounds (1-3) were tested for glycosidase inhibition.
Lohse
A
A
Department of Chemistry, Aarhus University, Denmark.
Ernholt
B V
BV
Bols
M
M
D001372:Aza Compounds / Q000737:chemistry* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050112:Imino Pyranoses; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry* / Q000494:pharmacology; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010880:Piperidines / Q000494:pharmacology; D011485:Protein Binding; D001617:beta-Glucosidase / Q000378:metabolism
D001372:Aza Compounds; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D009005:Monosaccharides; D010879:Piperazines; D010880:Piperidines; C098432:isofagomine; D006026:Glycoside Hydrolases; D001617:beta-Glucosidase