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目的:为增强异甘草素(Isoliquiritigenin,ILG,Ⅲ)的抗癌潜能,以它为先导化合物进行羟基化结构修饰,合成其衍生物3-羟基异甘草素(3-OH-ILG,Butein,Ⅴ)和3-甲氧基异甘草素(3-MO-ILG,Ⅶ),并进行结构表征。方法:利用羟醛缩合反应制备了3种目标化合物,并利用四大光谱法进行结构鉴定。各化合物的制备时,以2,4-二羟基苯乙酮(Ⅰ)为基准物,分别与对羟基苯甲醛(Ⅱ)、3,4-二羟基苯甲醛(Ⅳ)或香兰醛(Ⅵ)缩合而制得;此外,就各反应物的摩尔比、反应时间和温度对产率的影响进行简单的单因素考察。结果:化合物Ⅲ,Ⅴ和Ⅶ产率分别为45%,31%和36%;对化合物的理化性质和光谱特征进行系统描述;羟醛缩合反应最佳条件是:羟基苯乙酮与取代芳醛的摩尔比为1∶(2.5~3),120℃/6 h。结论:羟醛缩合反应是制备异甘草素衍生物的可行途径。反应物摩尔比、反应温度和时间是影响产率的主要因素;取代芳醛上羟基数目增多时,副反应发生率提高,产率下降。异甘草素衍生物的制备对生物活性研究和新型抗癌化合物的筛选奠定一定基础。
OBJECTIVE: To enhance the anti-cancer potential of isoliquiritigenin (ILG) and its precursor compound, hydroxylation of its derivatives 3-OH-ILG (Butein, V ) And 3-methoxy isoliquiritigenin (3-MO-ILG, Ⅶ) were synthesized and characterized. Methods: Three kinds of target compounds were prepared by aldol condensation reaction, and their structures were identified by four spectral methods. In the preparation of each compound, 2,4-dihydroxyacetophenone (Ⅰ) was used as the standard compound to react with p-hydroxybenzaldehyde (Ⅱ), 3,4-dihydroxybenzaldehyde (Ⅳ) ); In addition, simple single-factor investigation on the influence of the mole ratio of each reactant, reaction time and temperature on the yield was carried out. Results: The yields of compounds Ⅲ, Ⅴ and Ⅶ were 45%, 31% and 36% respectively. The physical and chemical properties and spectral characteristics of the compounds were systematically described. The optimum conditions for the aldol condensation reaction were as follows: Molar ratio of 1: (2.5 ~ 3), 120 ℃ / 6 h. Conclusion: Aldol condensation reaction is a viable route for the preparation of isoliquiritigenin derivatives. The molar ratio of reactants, reaction temperature and time are the main factors affecting the yield. When the number of substituted aromatic aldehydes increases, the incidence of side reactions increases and the yield decreases. The preparation of isoliquiritigenin derivatives has laid a foundation for the study of biological activity and screening of novel anticancer compounds.