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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (08): 1201-1211. 上一篇    下一篇

研究论文

1-(2-羟基苯甲酰基)-3-甲基-4-取代苯腙基-吡唑啉酮及其中间体的合成、表征及抑菌活性

邹敏1，卢俊瑞*,1，辛春伟1，鲍秀荣1，杨波2，朱姗姗1，刘倩1，李迎辉1，陶继强1   

  1. (1天津理工大学化学化工学院 天津300384)
    (2河南省医药科学研究院河南省肝病药理重点实验室 郑州450052)
  • 收稿日期:2009-12-11 修回日期:2010-01-20 发布日期:2010-03-31
  • 通讯作者: 卢俊瑞 E-mail:lujunrui@tjut.edu.cn
  • 基金资助:

    国家自然科学基金;国家自然科学基金;天津市高校科技发展基金

Synthesis, Characterization and Antibacterial Activities of 1-(2-Hydroxybenzoyl)-3-methyl-4-substituted phenylhydra-zono-pyrazolones and Their Intermediates

Zou Min1 Lu Junrui*,1 Xin Chunwei1 Bao Xiurong1 Yang Bo2 Zhu Shanshan1 Liu Qian1 Li Yinghui1 Tao Jiqiang1   

  1. (1 School of Chemistry and Chemical Engineering, Tianjin University of Technology, Tianjin 300384)
    (2 Henan Key Laboratory of Pharmacology of Liver Diseases, Henan Academy of Medical and Pharmaceutical Sciences, Zhengzhou 450052)
  • Received:2009-12-11 Revised:2010-01-20 Published:2010-03-31
  • Contact: Jun-Rui LU E-mail:lujunrui@tjut.edu.cn

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依据生物活性叠加原理, 将邻羟苯基、吡唑啉酮、苯腙基团进行合理组合, 构建并合成了2-取代苯腙基-3-(2-羟基苯甲酰腙基)-丁酸乙酯(3a～3f)和1-(2-羟基苯甲酰基)-3-甲基-4-取代苯腙基-吡唑啉酮(4a～4f)两类、共计12种化合物, 其中8种化合物未见报道, 12种化合物的抑菌活性均未见报道. 以芳胺为原料, 经重氮化、与乙酰乙酸乙酯反应, 与水杨酰肼缩合制得3a～3f, 3a～3f经分子内关环制得4a～4f, 化合物的结构经IR, 1H NMR, 元素分析等证实. 生物活性测试表明, 质量浓度为0.01%时, 化合物3b, 3c对大肠杆菌的抑菌率高达100%, 具有很强的抑菌活性; 化合物3a～3f对白色念珠菌、金黄色葡萄球菌的抑菌率均达70%以上, 具有较强的抑菌活性; 化合物4a～4f对白色念珠菌、大肠杆菌的抑菌率均接近或达到100%, 具有很强的抑菌活性, 对金黄色葡萄球菌的抑菌率均达78%以上, 具有较强抑菌活性; 与3a～3f相比, 形成吡唑啉酮环后的化合物4a～4f的抗菌活性更高.

关键词: 2-取代苯腙基-3-邻羟基苯甲酰腙基-丁酸乙酯, 1-邻羟基苯甲酰基-4-取代苯腙基-吡唑啉酮, 合成, 表征, 抑菌活性

A series of 1-(2-hydroxybenzoyl)-3-methyl-4-substituted phenylhydrazono-pyrazolones (4a～4f) and their intermediates 3a～3f were designed and synthesized by combining o-hydroxyl pheny, pyrazoleone and phenylhydrazone groups, according to the superposition principle of biological activities. Eight compounds and antibacterial-activity of all compounds have not been reported so far. Substituted anilines were diazotized and subsequently reacted with ethylacetoacetate, then condensed with salicylic hydrazide to obtain 3a～3f. The title compounds were acquired by intramolecular cyclization reaction of 3a～3f. The structures of all compounds were confirmed by IR, 1H NMR spectra and elemental analysis. The results of preliminary bioassay showed that the inhibitory rates against Escherichia coli of compounds 3b, 3c were high to 100% at 0.01% mass concentration, which displayed excellent antibacterial activities; and the inhibitory rates against Monilia albican and Staphlococcus aureus were over 70%, which exhibited a certain extent antibacterial activities. The inhibitory rates against Moniliaalbican and Escherichia coli of the compounds 4a～4f reached to 100% at 0.01% mass concentration, which displayed excellent antibacterial activities. The inhibitory rates against Staphlococcus aureus were over 78%, which exhibited a certain extent antibacterial activities. Comparing with those of 3a～3f, the inhibitory rates of the compounds 4a～4f were enhanced.

Key words: 2-phenylhydrazono-3-(o-hydroxybenzoylhydrazono)-ethyl butanoate, 1-(o-hydroxybenzoyl)-4- substituted phenylhydrazono-pyrazolone, synthesis, characterization, anti-bacterial-activity