Pyrrolidine iminosugars, sugar analogs (furanoside form) with the endocyclic oxygen
replaced by a nitrogen atom, are known as potent inhibitors of glycosidases and of other
glycoprocessing enzymes. Therefore their potential for a variety of medical applications (drugs
for metabolic disorders, antiviral and anticancer agents) makes them interesting as new
therapeutic leads.
Preparation of pyrrolidine iminosugars is challenging, involving low yield multistep
procedures and this is the reason why there are no systematic studies on the effect of
stereochemistry change at the chiral centers in the iminosugar ring. So, improved methods are
required for fast access to a series of these valuable biologically active compounds with
systematic structural or stereochemical changes in order to determine a structure – activity
relationship.
The synthesis of a series of pyrrolidines with varying stereochemistry using a protectivegroup
free approach involving the use of microwave/ultrasound activation and their
characterisation will be presented.
The in-house designed QSAR software PRECLAV (Property Evaluation by Class
Variables) estimated the main structural features important for the biological activity based on
the activity of a set of molecules (calibration set) reported in literature.