Stereoselective synthesis and glycosidase inhibitory activity of 3,4-dihydroxy-pyrrolidin-2-one, 3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one.
3,4-Dihydroxy-pyrrolidin-2-one, 3,4-dihydroxy-piperidin-2-one and 1,2-dihydroxy-pyrrolizidin-3-one have been synthesized, using a simple strategy based on the asymmetric dihydroxylation of vinylogous aminoesters and subsequent mild intramolecular cyclization. All these compounds show a partial inhibition of alpha-glucosidase, but were inactive towards other glycosidases.
Coutrot
Philippe
P
Laboratoire de Chimie Organique Biomoléculaire, UMR 7565, Université Henri Poincaré, Nancy 1, BP 239, 54506 Vandoeuvre-lès-Nancy, France.
Claudel
Stéphanie
S
Didierjean
Claude
C
Grison
Claude
C
D018360:Crystallography, X-Ray; D003500:Cyclization; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011760:Pyrrolidinones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C508207:1,2-dihydroxypyrrolizidin-3-one; C508206:3,4-dihydroxypiperidin-2-one; C508205:3,4-dihydroxypyrrolidin-2-one; D004791:Enzyme Inhibitors; D010880:Piperidines; D011758:Pyrroles; D011760:Pyrrolidinones; D006026:Glycoside Hydrolases