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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis and Antioxidant Properties of New Oxazole-5(4H)-one Derivatives
Canan Kuş1, Ezgi Uğurlu1, Elçin D Özdamar2
1Ankara University, Faculty Of Pharmacy, Department Of Pharmaceutical Chemistry, Ankara, Turkey.
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 1H 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.
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