Ultrasound-assisted synthesis, antimicrobial activity, DFT analysis, molecular docking, MD simulations, and pharmacokinetic profiling of 3-tosylbenzodoxazol-2(3H)-one

In this study, a series of N‑tosylated benzoxazolone derivatives (M1-M4) based on the 2(3H)-benzoxazolone scaffold were efficiently synthesized using a novel ultrasound‑assisted method, affording up to 93% yield in 5–20 min. This green, energy-efficient approach significantly outperformed conventional thermal synthesis in terms of reaction speed and selectivity. The structures of the products were confirmed by FT-IR, 1H NMR, 13C NMR spectroscopy, and GC-MS analyses. Biological evaluation of the derivatives identified the new compound M2 as the most active, showing strong antibacterial and antifungal effects. These results are consistent with its favorable electronic properties from DFT calculations and are further supported by molecular docking and MD simulations, which indicated stable binding to bacterial DNA gyrase. In silico ADMET analysis predicted that all compounds likely exhibit good drug‑likeness and acceptable pharmacokinetic properties, with M2 highlighted as a promising lead for further antimicrobial development.