Revisiting Purine Nucleoside Cholinesterase Inhibitors - An Experimental Glycon Structure/Activity Relationship Study.

N-glycosylation reaction was stereoselective for the β-anomers while regioselectivity was achieved for the N isomers when glycon positions 2 and 3 were methylated. Cholinesterase inhibition was found when the 2,3-di-O-benzyl-4-O-methyl pattern is present in the sugar moiety. Amongst the new compounds, the two most promising ones showed micromolar inhibition (mixed inhibition), being one of them selective for butyrylcholinesterase inhibition.