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Article Dans Une Revue Journal of Molecular Structure Année : 2022

New promising generation of phosphates α-aminophosphonates : Design, synthesis, in-vitro biological evaluation and computational study

Résumé

A novel category of phosphate-phosphonate compounds is synthesized by a sequence multicomponent reactions strategy of Kabachnik-Fields and Atherton-Todd reactions. All the designed products are obtained with good chemical yields in short reaction times, and confirmed by spectroscopy analyses. The diethyl [(4-diethylphosphate phenyl) (4-trifluoromethyl phenylamino) methyl] phosphonate 6g is characterized by single-crystal X-ray analysis. These compounds exhibited a strong antifungal effect, a low inhibition of AChE, and no inhibitory activity on BChE, with interesting antioxidant capacity. Results make them promising candidates as original organophosphorus pesticides. The DFT calculations concerning relative stability of various conformers, besides the comparison of the measured and calculated NMR spectra of selected compounds; suggest that conformational interconversion can quite easily occur in this type of molecules, so that many structures of the same compound can coexist in solution.

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hal-03815145 , version 1 (21-10-2022)

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Rim Aissa, Samia Guezane-Lakoud, Lynda Gali, Martial Toffano, Anna Ignaczak, et al.. New promising generation of phosphates α-aminophosphonates : Design, synthesis, in-vitro biological evaluation and computational study. Journal of Molecular Structure, 2022, 1247, pp.131336. ⟨10.1016/j.molstruc.2021.131336⟩. ⟨hal-03815145⟩
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