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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 9: 2581 - 2588

DOI: https://doi.org/10.6023/cjoc201903004

ARTICLE

Design, Synthesis and Biological Activity Screening of Novel Amide Derivatives Containing Aromatic Thioether Group

  • Hua Xuewen ,
  • Liu Nannan ,
  • Fan Zhijin ,
  • Zong Guangning ,
  • Ma Yi ,
  • Lei Kang ,
  • Yin Hao ,
  • Wang Guiqing
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  • a College of Agriculture, Liaocheng University, Liaocheng 252000;
    b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071;
    c College of Pharmacy, Liaocheng University, Liaocheng 252000

Received date: 2019-03-03

  Revised date: 2019-03-31

  Online published: 2019-04-19

Supported by

Project supported by the Natural Science Foundation of Shandong Province (No. ZR2017BC053), the Doctoral Research Startup Foundation of Liaocheng University (No. 318051625), and the Innovation and Entrepreneurship Training Program for College Students of Liaocheng University (No. CXCY2018181).

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Abstract

A series of amide derivatives containing aromatic sulfide and sulfone groups synthesized in our previous work displayed excellent nematocidal activity at 200 μg/mL. In order to explore the effect of structural modification of the amide bridge on biological activity in a more delicate way, two series of novel target compounds were designed and synthesized by adopting amide group flipping and introducing N-sulfonyl substituted amide bonds. The bioassays indicated that the structural modification of the amide bridge had important effects on their nematocidal and fungicidal activities, which the introduction of the N-sulfonyl substituent on the amide group was favorable to improving the nematocidal activity in comparison with compounds I. The molecular docking revealed that directly attaching the carbonyl or sulfonyl groups in the amide bridge to the aromatic rings was advantageous to the nematocidal activity.

Key words： synthesis; thioether; amide; nematocidal activity; molecular docking

Cite this article

Hua Xuewen , Liu Nannan , Fan Zhijin , Zong Guangning , Ma Yi , Lei Kang , Yin Hao , Wang Guiqing . Design, Synthesis and Biological Activity Screening of Novel Amide Derivatives Containing Aromatic Thioether Group[J]. Chinese Journal of Organic Chemistry, 2019 , 39(9) : 2581 -2588 . DOI: 10.6023/cjoc201903004

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