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

doi:10.6023/cjoc201712030

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (6): 1447-1453.DOI: 10.6023/cjoc201712030 Previous Articles Next Articles

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2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物的合成及抑菌活性

巫受群^a, 李小琴^a, 孟娇^b, 甘宜远^b, 田坤^a, 王贞超^b,c, 欧阳贵平^a,b,c

a 绿色农药与农业生物工程国家重点实验室培育基地教育部绿色农药与生物工程重点实验室贵州大学精细化工研究开发中心贵阳 550025;
b 贵州大学药学院贵阳 550025;
c 贵州省合成药物工程实验室贵阳 550025

收稿日期:2017-12-22 修回日期:2018-02-06 发布日期:2018-02-28
通讯作者: 王贞超,E-mail:oygp710@163.com;欧阳贵平,E-mail:wzc.4884@163.com E-mail:oygp710@163.com;wzc.4884@163.com
基金资助:
贵州省科技计划（No.20161055）、贵州省大学生创新创业（No.201610657052）和药用植物功效与利用国家重点实验室（No.201707）资助项目.

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

Received:2017-12-22 Revised:2018-02-06 Published:2018-02-28
Contact: 10.6023/cjoc201712030 E-mail:oygp710@163.com;wzc.4884@163.com
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).

1. Synthesis and Antibacterial Activity of 2-Morpholino-1-propyl-1H-indole-3-substituted Acylhydrazone Derivatives.PDF(1708KB)

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

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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]. Chin. J. Org. Chem., 2018, 38(6): 1447-1453.

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2-吗啉基-1-丙基-1H-吲哚-3-取代酰腙类化合物的合成及抑菌活性

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

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