Design, synthesis, molecular properties and in vitro antioxidant and antibacterial potential of novel enantiopure isoxazolidine derivatives

Abstract

A novel series of enantiopure isoxazolidines have been synthesized in good yields and with high stereoselectivity by 1,3-dipolar cycloaddition between a (–)-menthone-derived nitrone as a glycine equivalent and various terminal alkenes. The structures and the stereochemistry of the obtained cycloadducts have been determined by spectroscopic methods. Almost all the compounds were predicted to exhibit various degrees of antioxidant and antibacterial potentiality. Finally, the drug likeness and bioactivity were calculated using Molinspiration software. The results indicated that all compounds are in accordance with Lipinski’s rule of five showing good drug likeness and bioactivity score for drug targets with no violations. Keywords: (−)-Menthone, Chiral nitrone, Antioxidant capacity, Antibacterial potential, Molecular properties prediction, Drug likeness and bioactivity