Efficient synthesis, crystallography study, antibacterial/antifungal activities, DFT/ADMET studies and molecular docking of novel α-aminophosphonates

Rania Bahadi (1) , Malika Berredjem (1) , Chahrazed Benzaid (1) , Fouzia Bouchareb (1) , Ali Dekir (1) , Manel Lina Djendi (1) , Malika Ibrahim-Ouali (2, 3) , Meriem Boussaker (1) , Sofiane Bouacida (1) , Ajmal Rashid Bhat (1) , Sumeer Ahmed (1) , Khaldoun Bachari (1) , Rayenne Redjemia (1)

1 UBMA - Université Badji Mokhtar [Annaba]
2 AMU - Aix Marseille Université
3 ISM2 - Institut des Sciences Moléculaires de Marseille

An efficient method for the synthesis of a new series of α-aminophosphonates has been developed in a one-pot Kabachnik-Fields reaction of 4-methylaminophenol with various aldehydes and triethylphosphite under microwave irradiation and neat conditions using ZnO nanoparticles as a reusable and heterogeneous catalyst, with 82-93% yield at 250 Hz within 2-5 min. A single crystal of the studied compound 3e was selected for X-ray diffraction analysis, it crystallizes in the monoclinic crystal system with P 21/n space group. All the compounds were evaluated for their antimicrobial against a panel of Gram-negative pathogenic bacteria such as Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Serratia marcescens, Morganella morganii, Pseudomonas aeruginosa and Gram-positive :Staphylococcus aureus and against fungi : Candida albicans, Candida krusei, Candida kefyr, Candida lusitaniae, and Candida tropicalis. Further in silico target hunting reveals the antibacterial activity of the designed compounds by inhibiting Dihydropteroate synthase and all the designed compounds have shown significant drug-like characteristics.

Mots clés: А-aminophosphonates; RX study; Antibacterial activity; Antifungal activity; Molecular docking; Dft; ADMET

Domaines: Chimie

Rania Bahadi, Malika Berredjem, Chahrazed Benzaid, Fouzia Bouchareb, Ali Dekir, et al.. Efficient synthesis, crystallography study, antibacterial/antifungal activities, DFT/ADMET studies and molecular docking of novel α-aminophosphonates. Journal of Molecular Structure, 2023, 1289, pp.135849. ⟨10.1016/j.molstruc.2023.135849⟩. ⟨hal-04116317⟩