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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 6: 1447 - 1453

DOI: https://doi.org/10.6023/cjoc201712030

Articles

Synthesis and Antibacterial Activity of 2-Morpholino-1-propyl-1H-indole-3-substituted Acylhydrazone Derivatives

  • Wu Shouqun ,
  • Li Xiaoqin ,
  • Meng Jiao ,
  • Gan Yiyuan ,
  • Tian Kun ,
  • Wang Zhenchao ,
  • Ouyang Guiping
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  • a State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for Research of Fine Chemicals, Guizhou University, Guiyang 550025;
    b College of Pharmacy, Guizhou University, Guiyang 550025;
    c Drug Synthetic Engineering Laboratory of Guizhou Province, Guizhou University, Guiyang 550025

Received date: 2017-12-22

  Revised date: 2018-02-06

  Online published: 2018-02-28

Supported by

Project supported by the Guizhou Provincal Science Technology Program (No. 20161055), the Student Innovation and Entrepreneurship Project of Guizhou University (No. 201610657052), and the State Key Laboratory of Functions and Applications of Medicinal Plants (No. 201707).

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Abstract

A series of 2-morpholino-1-propyl-1H-indole-3-substituted acylhydrazone derivatives were designed and synthesized from oxindole. All the compounds were characterized by 1H NMR, 13C NMR and HRMS spectra, and their antibacterial activities were evaluated via turbidimeter test in vitro. The preliminary bioassay results indicated that all of the title compounds exhibited certain antibacterial activities in vitro against Xanthomonas axonopodis pv. Citri (X. citri), Ralstonia.solanacearum (R. solanacearum) and Xanthomonas oryzae pv. Oryzae (X. oryzae). These title compounds 2-cyano-N'-((2-morpholino-1-propyl-1H-indol-3-yl)methylene)acetohydrazide (12a), 4-chloro-N'-((2-morpholino-1-propyl-1H-indol-3-ylmethylene)ben-zohydrazide (12c), 4-fluoro-N'-((2-morpholino-1-propyl-1H-indol-3-yl)methylene)benzohydrazide (12f), N'-((2-morpholino-1-propyl-1H-indol-3-yl)methylene)-4-nitrobenzohydrazide (12k) and N'-((2-morpholino-1-propyl-1H-indol-3-yl)methylene) isonicotinohydrazide (12m) displayed good antibacterial activities. The concentration of 50% inhibition rate (EC50) of 12a, 12c, 12f, 12k and 12m against X. oryzae were 73.79, 61.94, 59.70, 36.72 and 82.79 μg/mL respectively, which was significantly superior to the control bismerthiazol and thiodiazole-copper (92.46 μg/mL and 120.22 μg/mL).

Key words： indole derivatives; acylhydrazone; acylhydrazine; antibacterial activity

Cite this article

Wu Shouqun , Li Xiaoqin , Meng Jiao , Gan Yiyuan , Tian Kun , Wang Zhenchao , Ouyang Guiping . Synthesis and Antibacterial Activity of 2-Morpholino-1-propyl-1H-indole-3-substituted Acylhydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(6) : 1447 -1453 . DOI: 10.6023/cjoc201712030

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