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新型恶唑-5(4)-酮衍生物的合成及其抗氧化性能

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

作者信息

Kuş Canan, Uğurlu Ezgi, Özdamar Elçin D, Can-Eke Benay

机构信息

Ankara University, Faculty Of Pharmacy, Department Of Pharmaceutical Chemistry, Ankara, Turkey.

Ankara University, Faculty Of Pharmacy, Department Of Pharmaceutical Toxicology, Ankara, Turkey.

出版信息

Turk J Pharm Sci. 2017 Aug;14(2):174-178. doi: 10.4274/tjps.70299. Epub 2017 Aug 15.

Abstract

OBJECTIVES

To synthesize and characterize 4-(substituted benzylidene)-2-(substituted phenyl)oxazol-5(4H)-one derivatives , and evaluate them for antioxidant activity.

MATERIALS AND METHODS

Required oxazole-5(4)-one derivatives were synthesized in two steps to obtain novel hippuric acid derivatives ; glycine and acylated appropriate benzoic acid derivatives were used and then, final compounds were obtained with condensation of with appropriate benzaldehydes . These products were purified by column chromatography using ethyl acetate/n-hexane as eluent. All the compounds were unequivocally characterized using the combination of H and C-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 .

RESULTS

The most active analogue on the microsomal EROD activity was which inhibited the microsomal EROD activity (89%) and was similarly better than that of the specific inhibitor caffeine (85%) at concentration.

CONCLUSION

The findings of this study indicate that the synthesized compounds, such as , display significant antioxidant activity.

摘要

目的

合成并表征4-(取代亚苄基)-2-(取代苯基)恶唑-5(4H)-酮衍生物,并评估其抗氧化活性。

材料与方法

通过两步合成所需的恶唑-5(4)-酮衍生物以获得新型马尿酸衍生物;使用甘氨酸和酰化的适当苯甲酸衍生物,然后通过与适当的苯甲醛缩合得到最终化合物。这些产物用乙酸乙酯/正己烷作为洗脱剂通过柱色谱法纯化。使用氢和碳核磁共振、质谱(ESI-MS)和元素分析相结合的方法对所有化合物进行了明确表征。在大鼠中测定脂质过氧化的抑制作用及其对肝细胞色素P450依赖性乙氧基异吩恶唑酮-O-脱乙基酶(EROD)的影响。

结果

对微粒体EROD活性最具活性的类似物是 ,其抑制微粒体EROD活性(89%),在 浓度下同样优于特异性抑制剂咖啡因(85%)。

结论

本研究结果表明,合成的化合物,如 ,具有显著的抗氧化活性。

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