Citation: 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 shu

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

Wu Shouqun ^a ,
Li Xiaoqin ^a ,
Meng Jiao ^b ,
Gan Yiyuan ^b ,
Tian Kun ^a ,
Wang Zhenchao ^b,c,, ,
Ouyang Guiping ^a,b,c,,

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

Corresponding author: Wang Zhenchao, oygp710@163.com Ouyang Guiping, wzc.4884@163.com
Received Date: 22 December 2017
Revised Date: 6 February 2018
Available Online: 28 June 2018
Fund Project: the State Key Laboratory of Functions and Applications of Medicinal Plants 201707the Guizhou Provincal Science Technology Program 20161055the Student Innovation and Entrepreneurship Project of Guizhou University 201610657052Project 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)

Figures(4)

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).
- indole derivatives,
- acylhydrazone,
- acylhydrazine,
- antibacterial activity
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