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咪唑并[1,2-a]吡啶化合物的无溶剂合成及其抗氧化性能
引用本文:席高磊,陈芝飞,杨金初,蔡莉莉,马波波,杨静,张晓平.咪唑并[1,2-a]吡啶化合物的无溶剂合成及其抗氧化性能[J].合成化学,2020,28(3):194-201.
作者姓名:席高磊  陈芝飞  杨金初  蔡莉莉  马波波  杨静  张晓平
作者单位:1. 河南中烟工业有限责任公司 技术中心,河南 郑州 450000; 2. 河南农业大学 烟草学院,河南 郑州 450002
基金项目:国家自然科学基金;河南农业大学基金资助项目
摘    要:无溶剂条件下,2-氨基吡啶、芳香醛和异氰基乙酸乙酯发生Groebke-Blackburn-Bienaymé三组分反应,高效合成了6个咪唑并1,2-a]吡啶化合物,产率89%~97%,其结构经1H NMR, 13C NMR和HR-MS(ESI)确证。并通过抑制HO·和还原型谷胱甘肽自由基(GS·)引发的DNA氧化反应体系,对化合物的抗氧化活性进行了检测。结果表明:在抑制HO·引发的DNA氧化反应体系中,6个化合物相对空白硫代巴比妥酸活性物质吸光度百分数(TBARS百分数)可达32.2%~72.1%;在抑制GS·引发的DNA氧化反应体系中,6个化合物的TBARS百分数可达34.8%~81.3%。

关 键 词:无溶剂合成  Groebke-Blackburn-Bienaymé反应  咪唑  抗氧化  自由基  TBARS百分数  
收稿时间:2019-09-25

Solvent Free Synthesis and Antioxidant Properties of Imidazo[1,2-a] pyridine Compounds
XI Gao-lei,CHEN Zhi-fei,YANG Jin-chu,CAI Li-li,MA Bo-bo,YANG Jing,ZHANG Xiao-ping.Solvent Free Synthesis and Antioxidant Properties of Imidazo[1,2-a] pyridine Compounds[J].Chinese Journal of Synthetic Chemistry,2020,28(3):194-201.
Authors:XI Gao-lei  CHEN Zhi-fei  YANG Jin-chu  CAI Li-li  MA Bo-bo  YANG Jing  ZHANG Xiao-ping
Institution:1. Technology Center, China Tobacco Henan Industrial Co.,Ltd., Zhengzhou 450000, China; 2. College of Tobacco Science, Henan Agricultural University, Zhengzhou 450002, China
Abstract:With 2-aminopyridine, the substituted aromatic aldehydes, and ethyl 2-isocyanoacetate as reactants, six imidazo1,2-a]pyridine compounds were synthesized via Groebke-Blackburn-Bienaymé three-component-reaction in the absence of solvents, and the yield were 89%~97%. The structures were confirmed by 1HNMR, 13CNMR, and HR-MS(ESI). Antioxidant abilities of the obtained compounds were evaluated by inhibiting Cu2+/glutathione(GSH)-and HO·-induced oxidation of DNA. The results showed that the TBARS percentages of six compounds were 32.2%~72.1% in inhibiting HO·-induced oxidation of DNA. The TBARS percentages of six compounds were 34.8%~81.3% in inhibiting GS·-induced oxidation of DNA.
Keywords:solvent free method  Groebke-Blackburn-Bienaymé reaction  imidazo  antioxidant  free radical  TBARS percentage
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