SnCl2-catalyzed Kabachnik-Fields of alfa-aminophosphonates with potent antioxidant activity

Abstract

A novel and efficient method for synthesizing a-aminophosphonates was developed through a Kabachnik–Fields multicomponent reaction using 6-aminocoumarin or 6-aminobenzodioxane, benzaldehyde, triethylphosphite, and a catalytic amount of SnCl2 in ethanol. The resulting 25 compounds 1a–l (71–92%) and 6a–m (45–96%) were obtained in moderate to excellent yields. Antioxidant activity, assessed via the FRAP andCUPRAC assays, the results demonstrated that several of these compounds exhibit comparable or evensuperior reducing power to ascorbic acid, particularly at low concentrations. These findings underscorethe potential of these a-aminophosphonates as promising antioxidant agents for future applications.ADME analysis predicts good oral bioavailability, limited brain and skin penetration, and potential CYP450inhibition.