260790-70-3Relevant academic research and scientific papers
Generalized Anomeric Effect in Action: Synthesis and Evaluation of Stable Reducing Indolizidine Glycomimetics as Glycosidase Inhibitors
Diaz Perez, Victor M.,Moreno, M. Isabel Garcia,Mellet, Carmen Ortiz,Fuentes, Jose,Diaz Arribas, Juan C.,Canada, F. Javier,Garcia Fernandez, Jose M.
, p. 136 - 143 (2000)
A series of aminoketalic castanospermine analogues incorporating a stereoelectronically anchored axial hydroxy group at the pseudoanomeric stereocenter (C-5) have been synthesized to satisfy the need for glucosidase inhibitors that are highly selective for α-glucosidases. The polyhydroxylated bicyclic system was built from readily available hexofuranose derivatives through a synthetic scheme that involved (i) the construction of a five-membered cyclic (thio)carbamate or (thio)urea moiety at the nonreducing end and (ii) the intramolecular nucleophilic addition of the heterocyclic thiocarbamic nitrogen atom to the masked aldehyde group of the monosaccharide. A biological screening of the resulting reducing 2-oxa- and 2-azaindolizidines against several glycosidase enzymes is reported.
