双酰胺类化合物抗氧化性能的研究

发布时间：2019-03-07 16:46

【摘要】：多组分反应在原子经济性、底物组合多样性,以及产物分子结构复杂性等方面均表现出无可比拟的优势。另一方面,作为生命科学领域中的重要课题之一,如何有效地抑制和清除人体内的有害自由基,吸引了人们的研究兴趣。采用生物抗氧化剂抑制及清除有害自由基,成为既具有理论研究意义,又具有潜在实用价值的课题。本论文采用Ugi四组分反应(Ugi 4CR)合成了11个双酰胺类化合物,此间将葡萄糖胺制成异腈,引入到分子结构中,既提高了双酰胺化合物的水溶性,又有利于加强双酰胺分子与生物基质的作用强度。与此同时,采用环己基异氰、金刚烷胺异氰和色胺异氰作为对比,以便从结构相似性角度确认葡萄糖基团对双酰胺类化合物抗氧化活性的影响。本论文采用3种方法表征了双酰胺类化合物的抗氧化活性:1.抑制过氧自由基引发的DNA氧化反应的能力;2.抑制Cu~(2+)/谷胱甘肽(GSH)引发的DNA氧化反应的能力;3.抑制·OH引发的DNA氧化反应的能力。在上述3个体系内的表征结果表明,不含酚羟基的双酰胺分子即便引入葡萄糖基团亦不能产生抑制DNA氧化反应的活性,将葡萄糖异腈与没食子酸、阿魏酸、咖啡酸,以及对-羟基苯甲酸等抗氧化活性羧酸,发生Ugi 4CR生成双酰胺,便显现出良好的抗氧化活性,并且双酰胺的抗氧化活性高于原来的羧酸。由此说明,一方面酚羟基仍为双酰胺类化合物的抗氧化官能团,另一方面引入葡萄糖基团提高了双酰胺类化合物的抗氧化活性。因此,充分利用葡萄糖基团潜在的与生物基质之间的相互作用,为构建生物抗氧化分子提供一条新的研究思路。
[Abstract]:Multi-component reactions show unparalleled advantages in atomic economy, substrate combination diversity, and the complexity of the molecular structure of the products. On the other hand, as one of the important topics in the field of life science, how to effectively suppress and eliminate harmful free radicals in human body has attracted people's interest in research. The use of biological antioxidants to inhibit and eliminate harmful free radicals has both theoretical significance and potential practical value. In this paper, 11 biamides were synthesized by UGI four-component reaction (Ugi 4CR), in which glucosamine was used to form isonitrile, which was introduced into the molecular structure to improve the water solubility of biamides. It is also beneficial to strengthen the interaction strength between biamide molecule and bio-matrix. At the same time, Cyclohexyl isocyanide, amantadine isocyanide and tryptamine isocyanide were used as comparison to confirm the effect of glucose groups on the antioxidation activity of biamides from the point of view of structural similarity. In this paper, the antioxidant activity of biamides was characterized by three methods: 1. The ability to inhibit the oxidation of DNA induced by peroxy radical; 2. Ability to inhibit the oxidation of DNA initiated by Cu~ (2) / glutathione (GSH); 3. The ability to inhibit the oxidation of DNA initiated by OH. The characterization results in the above three systems showed that even the introduction of glucose group into the biamide molecule without phenol hydroxyl group could not produce the activity to inhibit the oxidation of DNA. The isonitrile of glucose, Gallic acid, ferulic acid, caffeic acid, and so on, could not inhibit the oxidation reaction of Glucoisonitrile, ferulic acid and caffeic acid. And p-hydroxybenzoic acid and other anti-oxidation active carboxylic acids, the formation of Ugi 4CR produced biamides, showed a good antioxidant activity, and the antioxidation activity of biamides is higher than the original carboxylic acids. Therefore, on the one hand, phenolic hydroxyl group is still the antioxidant functional group of biamides, on the other hand, the introduction of glucose group improves the antioxidant activity of biamides. Therefore, making full use of the potential interaction between glucose group and biological matrix provides a new research idea for the construction of biological antioxidant molecules.
【学位授予单位】：吉林大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O623.626

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