383369-30-0Relevant academic research and scientific papers
Synthesis and evaluation of calystegine B2 analogues as glycosidase inhibitors
Garcia-Moreno,Benito,Mellet,Fernandez
, p. 7604 - 7614 (2001)
A practical synthesis of polyhydroxylated 6-oxa-nor-tropanes incorporating the essential structural features of calystegine B2 from 5-deoxy-5-thioureido and 5-ureido-L-idofuranose precursors is presented. The methodology relies on the ability of pseudoamide-type nitrogen atoms (thiourea, urea, and carbamate) to undergo nucleophilic addition to the masked aldehyde group of the monosaccharide. The generated hemiaminal functionality may further undergo in situ intramolecular glycosidation to give the bicyclic aminoacetal compounds, the whole process being favored by the anomeric effect. A series of derivatives bearing different substituents at nitrogen has been prepared and screened against several glycosidases in comparison with xylonojirimycin-type piperidine analogues. Interestingly, strong and highly specific inhibition of bovine liver β-glucosidase was observed for 6-oxacalystegine B2 analogues incorporating aromatic pseudoaglyconic groups. On the basis of these data, a 1-azasugar inhibition mode is proposed for this family of glycomimetics.
Synthesis and biological evaluation of guanidine-type iminosugars
Aguilar, Matilde,Diaz-Perez, Paula,Garcia-Moreno, M. Isabel,Mellet, Carmen Ortiz,Garcia Fernandez, Jose M.
, p. 1995 - 1998 (2008/09/18)
(Chemical Equation Presented) The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose → piperidine rearrangement of 5-deoxy-5-guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.
