Design, synthesis and molecular docking study of novel bis-oxazolone derivatives as potent antioxidant and antibacterial agents

Abstract

In response to the challenge of antibiotic-resistant microorganisms, oxazolone analogs are frequently used for bacterial, antiviral, and anti-inflammatory treatments. However, few studies have shown bis-oxazolone analogs possess antibacterial activities. In this study, we modified bis-oxazolone molecules with various aromatic amines to create new bis-benzamide and bis-imidazolone derivatives. These derivatives were analyzed using FT-IR, ¹H-NMR, and ¹³C-NMR spectroscopy. Molecular docking revealed favorable interactions with DNA gyrase, with compounds 3, 4a, and 5e showing higher binding affinities than penicillin G and ampicillin. These findings suggest their potential as future antimicrobial agents. The tested compounds demonstrated efficacy against bacterial strains, particularly E. coli and S. aureus, with significant activity observed in compounds 4a, 4e, 5d, and 5e. Antioxidant activity, assessed using the DPPH method, showed bis-compounds with excellent results comparable to ascorbic acid. This encourages further studies to explore their potential. Overall, the synthesized bis-oxazolone derivatives demonstrated increased medicinal activity and high potential as future antimicrobial and antioxidant agents. KEY WORDS: Bis-oxazolone, Bis-benzamide, Bis-imidazolone, Docking study, Antibacterial, Antioxidant Bull. Chem. Soc. Ethiop. 2024, 38(5), 1393-1404.                                                            DOI: https://dx.doi.org/10.4314/bcse.v38i5.15