PROTIC IONIC LIQUIDS IN THE SYNTHESIS OF ANALOGS OF IMMUNOSTIMULANT PLERIXAFOR

Abstract

To date, a variety of plerixafor structural analogs containing a p-xylylenediamine fragment are known. Some of them exhibit biological activitysimilar to that of the original drug. We have synthesized new structural analogs of plerixafor, in which both cyclam fragments are replaced by other nitrogen-containing moieties, such as cyclic or acyclic amines and amides. The syntheticprocedure included a double donor–acceptor cyclopropane ring-opening with nitrogen-containing nucleophiles (azide, thiocyanate, etc.) in protic ionic liquid media acting as both a solvent and an acidic catalyst followed by post-modifications.