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依据生物活性叠加原理,以邻羟苯基和苯基吡唑为分子核心,构建了6种未见报道的N-[(1-芳基-3-苯基-吡唑-4-基)次甲基]-2-羟基苯甲酰肼衍生物.以芳胺为原料,经重氮化、还原、与苯乙酮缩合及Vilsmeier-Haack反应制得1-芳基-3-苯基-4-甲酰基吡唑,再与水杨酰肼反应制得目标化合物,其结构经IR,1HNMR和元素分析等验证.探讨了制备中间体(3a～3f)的反应机理,结果表明,1位芳环上取代基对关环反应有显著影响,供电基有利于关环反应的进行,吸电基则恰恰相反.抗菌活性测试表明,质量分数为0.01%的化合物对大肠杆菌和白色念珠菌的抑菌率高达100%,有极强的抑菌活性,对金黄色葡萄球菌的抑菌率达70%以上,有一定的抑菌活性,是一类极具潜力的抗真菌和抗革兰氏阴性菌的化合物.构效分析结果表明,1位芳基中引入Cl和Br等卤原子,能显著增强化合物的抑菌活性,而引入NO2和CH3基团,则会降低其抑菌活性.
According to the principle of superposition of biological activities, six newly reported N - [(1-aryl-3-phenyl-pyrazol-4-yl) Methyl] -2-hydroxybenzohydrazide.Aromatic amines as raw materials, diazotization, reduction, condensation with acetophenone and Vilsmeier-Haack reaction 1-aryl-3-phenyl-4 - formylpyrazole, and then reacted with salicyloyl hydrazide to obtain the target compound, its structure was confirmed by IR, 1HNMR and elemental analysis. The reaction mechanism of the preparation of intermediates (3a ~ 3f) was discussed. The results showed that the Substituents have a significant effect on the ring closure reaction, while the electricity supply is conducive to the ring closure reaction, while the electricity-absorbing group is the opposite .Antibiotic activity test showed that the antibacterial activity of the compound with 0.01% of mass fraction against E.coli and Candida albicans Up to 100%, has a strong antibacterial activity, the antibacterial rate of Staphylococcus aureus up to 70%, has some antibacterial activity, is a very potential anti-fungal and Gram-negative bacteria The results of structure-activity analysis showed that the introduction of halogen atoms such as Cl and Br in the aryl group of 1 can significantly enhance the antibacterial activity of the compounds, while the introduction of NO2 and CH3 groups will reduce Its antibacterial activity.