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有机化学
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有机化学 ›› 2018, Vol. 38 ›› Issue (11): 3016-3025.DOI: 10.6023/cjoc201805038 上一篇    下一篇

研究论文

苯并[h]喹啉腙类化合物的合成及生物活性研究

时蕾, 徐晶晶, 毕晶晶, 张志国, 刘统信, 杨晓岚, 张贵生   

  1. 河南省有机功能分子和药物创新重点实验室 河南师范大学化学化工学院 新乡 453007
  • 收稿日期:2018-05-17 修回日期:2018-06-05 发布日期:2018-07-16
  • 通讯作者: 张贵生 E-mail:zgs@htu.cn
  • 基金资助:

    国家自然科学基金（Nos.21605039，21702051）、河南省高等学校重点科学研究计划（Nos.18A150009，17A350006）和河南师范大学青年科学基金（No.2016QK10）资助项目.

Synthesis and Biological Activity of Benzo[h]quinolinium Hydrazine Compounds

Shi Lei, Xu Jingjing, Bi Jingjing, Zhang Zhiguo, Liu Tongxin, Yang Xiaolan, Zhang Guisheng   

  1. Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007
  • Received:2018-05-17 Revised:2018-06-05 Published:2018-07-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21605039, 21702051), the Key Scientific Research Project of Henan Provinc (Nos. 18A150009, 17A350006), the Henan Normal University Science Foundation for Young Scholars (No. 2016QK10)

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补充材料

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喹啉类衍生物、芳腙以及酰腙类化合物都具有显著的生物活性，以1-萘胺、取代苯甲醛和丙酮酸甲酯为起始原料经Doebner-Miller反应生成苯并[h]喹啉甲酸甲酯，酯还原后再氧化得到相应的醛.取代苯并[h]喹啉甲醛分别与肼盐和酰肼反应合成苯并[h]喹啉腙及酰腙类化合物.初步活性数据表明大部分化合物对细胞周期分裂蛋白25B（CDC 25B）和蛋白酪氨酸磷酸酶PTP 1B表现出较显著的抑制活性.

关键词: 苯并[h]喹啉衍生物, 腙, 酰腙, CDC 25B, PTP 1B, 抑制活性

Quinoline derivatives, aryl hydrazines and hydrazide compounds have significant biological activities. Benzo[h] quinoline derivatives were synthesized from 1-naphthylamine, substituted benzaldehyde and methyl pyruvate by Doebner-Miller reaction. After the ester was reduced, the corresponding aldehyde was obtained by oxidation. Benzo[h] quinolinium and quinoline hydrazide compounds were synthesized by reacting benzo[h] quinoline formaldehyde with hydrazine salts and hydrazides, respectively. The preliminary activity data showed that most of the compounds exhibited significant inhibitory activities against cycle protein 25B (CDC 25B) and protein tyrosine phosphatase PTP 1B.

Key words: Benzo[h]quinoline derivatives, hydrazone, hydrazide, CDC 25B, PTP 1B, inhibitory activity