Synthesis and Antioxidant Properties of New Oxazole-5(4 H )-one Derivatives

[摘要] Objectives: To synthesize and characterize 4-(substituted benzylidene)-2-(substituted phenyl)oxazol-5(4H)-one derivatives (E1-E10), and evaluate them for antioxidant activity. Materials and Methods: Required oxazole-5(4H)-one derivatives were synthesized in two steps to obtain novel hippuric acid derivatives (7-13); glycine and acylated appropriate benzoic acid derivatives were used and then, final compounds were obtained with condensation of 7-13 with appropriate benzaldehydes (E1-E10). These products were purified by column chromatography using ethyl acetate/n-hexane as eluent. All the compounds were unequivocally characterized using the combination of 1 H and 13C-nuclear magnetic resonance, mass spectrometry (ESI-MS), and elemental analysis. The inhibition of lipid peroxidation and its effects on hepatic cytochrome P450-dependent ethoxyresorufin-O-deethylase (EROD) enzyme were determined in rats in vitro. Results: The most active analogue on the microsomal EROD activity was E3 which inhibited the microsomal EROD activity (89%) and was similarly better than that of the specific inhibitor caffeine (85%) at 10-3 M concentration. Conclusion: The findings of this study indicate that the synthesized compounds, such as E3, display significant antioxidant activity.

[关键词] Oxazolidinones;synthesis;antioxidant activity;lipid peroxidation;EROD activity