Combined Chemical, Biological and Theoretical DFT-QTAIM Study of Potent Glycosidase Inhibitors Based on Quaternary Indolizinium Salts (pages 5498–5514)
Peter Šafář, Jozefína Žúžiová, Štefan Marchalín, Nadežda Prónayová, Ľubomír Švorc, Viktor Vrábel, Sergej Šesták, Dubravko Rendić, Vincent Tognetti, Laurent Joubert and Adam Daïch
Article first published online: 15 AUG 2012 | DOI: 10.1002/ejoc.201200431
Six novel enantiopure indolizidinediols have been synthesized with regioselective THF ring opening as a key step. These substrates and others were then quaternized. The stereochemistry of these reactions was elucidated by NMR, X-ray diffraction, and a combined DFT-QTAIM study. Inhibitory assays were performed with six indolizidines and two derivatives exhibited pH-dependent inhibition of dGMIIb.