<p>Derivatives of prepared nitrogen-based heterocycles hydroxyquinolone underwent an antioxidant activity evaluation through in vitro DPPH and ABTS assays. Several compounds were able to exhibit potent radical scavenging with compounds 6a and 6e presenting the most encouraging results with promising IC₅₀ values in both assays. The exploring of the antioxidant activity of hydroxyquinolone derivatives was broaden by performing a docking study in which their binding mode within the cavity of an antioxidant drug target; xanthine oxidase (XO) enzyme was predicted. Results were promising for the studied derivatives especially compounds 6c and 6e that exhibited significant stability highlighted by good docking scores. The stability of the compounds inside the active pocket of XO was enhanced by the formation of different interactions comprising H-bonds with key residues such as Lys771. The ligands presenting the best molecular docking results (6c and 6e) in complex with XO were subjected to molecular dynamics simulation using Desmond. During the simulation, the two studied complexes demonstrated substantial stability after the initial first nanoseconds. Furthermore, Hirshfeld surface analysis helped quantifying the interaction perceived in two derivatives of hydroxyquinolones. Additionally, ADME-related parameters were predicted and ensured the oral bioavailability of most compounds as well as their ability to cross biological membranes giving them improved pharmacokinetic properties.</p> Graphical Abstract <p></p>