Polyhydroxylated homoazepanes and 1-deoxy-homonojirimycin analogues: Synthesis and glycosidase inhibition study.
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.
Markad
Shankar D
SD
Garware Research Centre, Department of Chemistry, University of Pune, Pune, 411 007, India.
Karanjule
Narayan S
NS
Sharma
Tarun
T
Sabharwal
Sushma G
SG
Dhavale
Dilip D
DD
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
D001381:Azepines; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases