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目的合成具有新型结构的系列卤酚类化合物,测定其体外抗氧化活性并初步探讨其构效关系。方法以取代苯甲酸或苯甲酰氯为原料,经多步反应制得卤酚类化合物,并通过DPPH(二苯代苦味肼基)自由基清除实验测定其抗氧化活性。结果与结论合成了9个新化合物,其结构经ESI-MS、1H-NMR、13C-NMR确证,总收率70%～91%。体外活性实验表明,抗氧化活性与羟基和卤原子的数目与位置有关;化合物5c,5c′,8b,8c的抗氧化活性优于常用抗氧化剂BHT(二丁基羟基甲苯)。
OBJECTIVE: To synthesize a series of halogenated phenolic compounds with novel structure and to determine their in vitro antioxidant activities and to explore their structure-activity relationship. Methods The substituted benzoic acid or benzoyl chloride was used as the raw material to obtain the halo-phenol compounds by multi-step reaction. The antioxidant activity of the compounds was determined by DPPH radical scavenging. RESULTS AND CONCLUSION Nine new compounds were synthesized and their structures were confirmed by ESI-MS, 1H-NMR and 13C-NMR. The overall yield was 70% ~ 91%. In vitro activity tests showed that the antioxidant activity was related to the number of hydroxyl groups and halogen atoms. The anti-oxidative activity of 5c, 5c ’, 8b, 8c was better than BHT (dibutylhydroxytoluene).