Design, synthesis and cytotoxicity of a new series of isoxazolidines derived from substituted chalcones

A new series of isomeric isoxazolidin-3-yl-3-phosphonates were synthesised from N-methyl-C-diethoxyphosphorylnitrone and substituted chalcones. The respective isoxazolidin-3-yl-3-phosphonic acids were obtained from phosphonates via dealkylation procedure using trimethylsilyl bromide. Selected phosphonates and their respective phosphonic acids were screened for their cytotoxic activity to HeLa and K562 cells with IC50 in the 0.1–0.3 mM range.

Graphical abstractCytotoxic activity against HeLa and K562 cells line of several chalcone-like isoxazolidine-3-yl-3-phosphonates was evaluated with IC50 values reaching the 0.1–0.3 mM range.Figure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Chalcone framework incorporated into isoxazolidine-3-yl-3-phosphonate skeleton. ► 1,3-Dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and chalcones lacks regioselectivity. ► Cytotoxic substituted isoxazolidine-3-yl-3-phosphonates.