title: Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: Synthesis and glycosidase inhibition study.
abstract: The Johnson-Claisen rearrangement of D-gluco and L-ido-derived allylic orthoesters afforded gamma,delta-unsaturated ester that on ester reduction, epoxidation, regioselective oxirane opening by sodium azide and hydrogenation led to sugar amino alcohols--immediate precursors for 1-deoxy-homonojirimycin 3a,b, and polyhydroxylated homoazepanes 4a,b. Our synthetic approach and glycosidase inhibitory activity is reported.
authors.affiliation: Garware Research Centre, Department of Chemistry, University of Pune, Pune, 411 007, India.
authors.forename: Shankar D
authors.initials: SD
authors.lastname: Markad
authors.forename: Narayan S
authors.initials: NS
authors.lastname: Karanjule
authors.forename: Tarun
authors.initials: T
authors.lastname: Sharma
authors.forename: Sushma G
authors.initials: SG
authors.lastname: Sabharwal
authors.forename: Dilip D
authors.initials: DD
authors.lastname: Dhavale
mesh_terms: D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002417:Cattle; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006900:Hydroxylation / Q000187:drug effects; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D010944:Plants / Q000201:enzymology; D015003:Yeasts / Q000201:enzymology
chemical_list: D001381:Azepines; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases