Click chemistry: In vitro evaluation of glycosyl hybrid phosphorylated/thiophosphorylated 1,2,3-triazole derivatives as irreversible acetyl cholinesterase (AChE) inhibitors

Abstract

A novel series of phosphorylated/ thiophosphorylated glucosyl-1,2,3-triazole derivatives have been synthesized in three step process. The synthetic approach was progressed from the reaction of propargyl alcohol with dialkoxychlorophosphate/thiophosphate derivatives to give propargylphosphate/thiophosphate derivatives. Then, the reaction of above synthesized compounds with acetylated glucosyl azides through azide-alkyne [2 + 3]-cycloaddition reaction (click reaction) led to the formation of the title phosphorylated/thiophosphorylated glucosyl-1,2,3-triazole derivatives in good yields. The synthesized compounds are subjected to biological evaluation as acetyl cholinesterase (AChE) inhibitors and the results are compared with reported compounds.

Keywords

• Glucosides
• 1,2,3-Triazole
• Click chemistry
• Organophosphorous
• Cycloaddition