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2019 , Vol. 39 >Issue 10: 2851 - 2859

DOI: https://doi.org/10.6023/cjoc201904049

研究论文

含二苯醚结构的联苯胺类衍生物的合成及活性研究

  • 汪万强 ,
  • 程兰 ,
  • 彭宏英 ,
  • 姚维忠 ,
  • 张锐 ,
  • 陈宬 ,
  • 程华
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  • a 湖北文理学院化学化工与食品科学学院 襄阳 441053
    b 武汉理工大学材料复合新技术国家重点实验室 武汉 430070

收稿日期: 2019-04-19

  修回日期: 2019-05-23

  网络出版日期: 2019-06-06

基金资助

国家自然科学基金(21502062);湖北文理学院教师科研能力培育基金(2018kypy001);湖北文理学院学科开放基金资助项目(XK2019039)

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Synthesis and Biological Activities of New 4-PhenylanilinesContaining the Diphenyl Ether Moiety

  • Wanqiang Wang ,
  • Lan Cheng ,
  • Hongying Peng ,
  • Weizhong Yao ,
  • Rui Zhang ,
  • Cheng Chen ,
  • Hua Cheng
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  • a Department of Chemical Engineering and Food Science, Hubei University of Arts and Science, Xiangyang 441053
    b State Key Laboratory of Advanced Technology for Materials Synthesis and Processing,Wuhan University of Technology, Wuhan 430070

Received date: 2019-04-19

  Revised date: 2019-05-23

  Online published: 2019-06-06

Supported by

Project supported by the National Natural Science Foundation of China(21502062);The Teachers' Scientific Research Ability Cultivation Fund of Hubei University of Arts and Science(2018kypy001);The Open Foundation of Discipline of Hubei University of Arts and Science(XK2019039)

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摘要

采用活性亚结构拼接的方法将二苯醚活性结构单元引入到联苯胺的结构中, 设计并合成了一系列未见文献报道的新型含二苯醚结构的联苯胺类衍生物. 此外, 所得目标化合物的结构经 1H NMR、 13C NMR、高分辨质谱(HRMS)及熔点(m.p.)确认. 测试了该类化合物对猪心来源琥珀酸-细胞色素c氧化还原酶(SCR)的抑制活性, 活性结果表明: N-{4-[2-氯-4-(三氟甲基)苯氧基]-3-氟苯基}-[1,1'-联苯]-4-胺(3o)的抑制活性较好, 抑制率达到了46.44%.

关键词： 联苯胺; 二苯醚; 合成; 生物活性

本文引用格式

汪万强 , 程兰 , 彭宏英 , 姚维忠 , 张锐 , 陈宬 , 程华 . 含二苯醚结构的联苯胺类衍生物的合成及活性研究[J]. 有机化学, 2019 , 39(10) : 2851 -2859 . DOI: 10.6023/cjoc201904049

Abstract

According to the principle of "splicing-up" bioactive substructures, a new series of target compounds were designed and synthesized by incorporating a diphenyl ether moiety into 4-phenylanilines. Moreover, the structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, HRMS and melting points measurements. The inhibitory activities of these compounds were evaluated against succinate-cytochrome reductase (SCR). Based on the bioassay results, target compound N-(4-(2-chloro-4-(trifluoromethyl)phenoxy)-3-fluorophenyl)-[1,1'-biphenyl]-4-amine (3o) exhibited an inhibition rate of 46.44% at a concentration of 10 μmol?L –1, which demonstrated potential values for further investigations.

Key words： 4-phenylanilines; diphenyl ether; synthesis; biological activities

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