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    Eco-friendly synthesis of α-aminophosphonates using ultrasound irradiation: In vitro pharmacological studies and molecular docking approach
    (Elsevier, 2026) Badaoui, Kawther; Sehout, Imene; Sekerci, Guldeniz; Keskin, Tuba; Tekin, Suat; Hamlaoui, Ikram; Kucukbay, Hasan
    A series of novel alpha-aminophosphonates 4a-m have been successfully synthesized via Kabachnik-Fields reaction under ultrasound irradiation and in the presence of acetylsalicylic acid as catalyst with yields ranging 69-87 %. All compounds were characterized by 1H, 13C, 31P, FTIR and elemental analysis. Anticancer activity was evaluated using three cancer cell lines (MCF-7, A2780, Caco-2). Compounds 4k, 4h and 4e exhibited good cytotoxic activity against MCF-7. The in vitro antioxidant activity of the synthesized molecules was evaluated by four complementary methods (DPPH, ABTS, FRAP and Phenanthroline). Compound 4c and 4f showed high antioxidant capacity at ABTS scavenging assay, while compounds 4a, 4b, 4c, 4d, 4e and 4f showed high antioxidant capacity at Phenanthroline assay. The target molecules showed moderate antifungal activity against the phytopathogenic strain Fusarium oxysporum f.sp. lycopersici (FOL). Compounds 4e, 4h, and 4k, that showed the best the highest activity against breast cancer (MCF-7), were further analyzed through molecular docking to investigate their modes of interaction with two enzymes implicated in this cancer.
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    Ultrasound-promoted one-pot synthesis of α-aminophosphonates: X-ray crystallographic study and biological screening
    (Taylor & Francis Ltd, 2026) Sehout, Imene; Badaoui, Kawther; Kucukbay, Hasan; Nemouchi, Sara; Bendjeddou, Lamia; Bensouici, Chawki; Debbi, Ali
    A green and efficient approach was developed for the synthesis of twenty-three alpha-aminophosphonate derivatives (4a-4v) via the Kabachnik-Fields reaction, using acetylsalicylic acid as a novel eco-friendly Br & oslash;nsted acid catalyst under ultrasound irradiation and solvent-free conditions. The target compounds were obtained in moderate to excellent yields (43 - 91%) and were structurally characterized by FTIR, 1H NMR, 13C NMR, and single-crystal X-ray diffraction analysis. Notably, the crystal structure of compound 4c was elucidated by X-ray diffraction, providing detailed molecular and supramolecular insights. The antioxidant activity of the synthesized compounds was evaluated through four in vitro assays (DPPH, ABTS, FRAP, and phenanthroline), with compounds 4a, 4c, 4d, and 4k demonstrating significant potency. Additionally, antifungal activity was assessed against Fusarium oxysporum f. sp. lycopersici, with compound 4t exhibiting the highest inhibitory effect.