697288-29-2Relevant academic research and scientific papers
Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases
Garcia-Moreno, M. Isabel,Rodriguez-Lucena, David,Ortiz Mellet, Carmen,Garcia Fernandez, Jose M.
, p. 3578 - 3581 (2007/10/03)
Coupling reaction of (2R,3R,4R,5R)-2,5-hydroxy-methyl-3,4-dihydroxypyrrolidine (DMDP) with isothiocyanates afforded the corresponding thiourea adducts, which were transformed into isourea-type bicyclic oxapyrrolizidine glycomimetics by mercury(II) oxide-assisted intramolecular sulfur displacement. Cyclic carbamate and thiocarbamate analogues were also prepared by direct carbonylation or thiocarbonylation of DMDP. Evaluation of the glycosidase inhibitory properties demonstrated that remarkable specificities in enzyme inhibition can be achieved upon modifications on the pseudoaglyconic side chain and on the nature of the sp2-hybridized endocyclic ring nitrogen.
