Eco-friendly synthesis of α-aminophosphonates using ultrasound irradiation: In vitro pharmacological studies and molecular docking approach

Badaoui K., Sehout I., Şekerci G., Keskin T., TEKİN S., Hamlaoui I., ...Daha Fazla

Journal of Molecular Structure, cilt.1352, 2026 (SCI-Expanded, Scopus) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1352
  • Basım Tarihi: 2026
  • Doi Numarası: 10.1016/j.molstruc.2025.144479
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: Acetylsalicylic acid, Anticancer activity, Antifungal activity, Antioxidant activity, Molecular docking, Ultrasound irradiation, α-aminophosphonates
  • İnönü Üniversitesi Adresli: Evet

Özet

A series of novel α-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.