高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (8): 1683-1690.doi: 10.7503/cjcu20180081

• 有机化学 • 上一篇    下一篇

含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物的合成及抗细菌活性

万金林1, 巫受群1, 甘宜远2, 孟娇2, 王贞超2(), 欧阳贵平2()   

  1. 1.绿色农药与农业生物工程国家重点实验室培育基地, 绿色农药与农药生物工程教育部重点实验室,贵州大学精细化工研究开发中心, 2. 药学院, 贵阳 550025
  • 收稿日期:2018-01-25 出版日期:2018-08-10 发布日期:2018-05-27
  • 作者简介:联系人简介: 欧阳贵平, 男, 博士, 教授, 博士生导师, 主要从事新农药和新医药创制方面的研究. E-mail: oygp710@163.com; 王贞超, 女, 博士, 副教授, 主要从事新农药和新医药创制方面的研究. E-mail: wzc.4884@163.com
  • 基金资助:
    贵州省科技计划项目(批准号: 20161055)、 贵州省教育厅青年科技人才成长项目(批准号: 黔教合KY字[2017]115)和药用植物功效与利用国家重点实验室资助项目(批准号: 201707)资助.

Synthesis and Antibacterial Activities Evaluation of Chalconesemicarbazone Derivatives Bearing 1,3,4-Thiadiazole Moiety

WAN Jinlin1, WU Shouqun1, GAN Yiyuan2, MENG Jiao2, WANG Zhenchao2*(), OUYANG Guiping2*()   

  1. 1. 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,2. College of Pharmacy, Guizhou University, Guiyang 550025, China
  • Received:2018-01-25 Online:2018-08-10 Published:2018-05-27
  • Supported by:
    † Supported by the Guizhou Provincial Science and Technology Program of China(No. 20161055), the Young Talents Scientific Research Foundation of Guizhou Education Department of China(No. KY[2017]115) and the Project of State Key Laboratory of Functions and Applications of Medicinal Plants of China(No. 201707).

摘要:

以苯甲醛和1,3,4-噻二唑为起始原料, 设计合成了一系列新颖的含1,3,4-噻二唑结构的查尔酮缩氨基脲类化合物. 利用核磁共振波谱(NMR)和高分辨质谱(HRMS)对其结构进行了确证. 初步抑菌活性测试结果表明, 该类化合物对水稻白叶枯病菌(X. oryzae)、 烟草青枯病菌(R. solanacearum)和柑橘溃疡病菌(X. citri)均表现出一定的抑制活性, 其中化合物7h和7i在浓度为100 μg/mL时, 对以上3种植物病菌的抑制率均达到100%, EC50值分别为15.13, 30.90, 24.49和21.33, 24.54, 14.79 μg/mL, 均超过对照药叶枯唑(EC50值分别为92.23, 58.88和123.02 μg/mL).

关键词: 1,3,4-噻二唑, 查尔酮缩氨基脲, 抑菌活性

Abstract:

A series of chalconesemicarbazone derivatives bearing a 1,3,4-thiadiazole moiety was designed and synthesized from benzaldehyde and 1,3,4-thiadiazole. All the target compounds were characterized by means of nuclear magnetic resonance and high resolution mass spectrometer. The preliminary bioassay results indicated that all the title compounds exhibited a certain antibacterial activities in vitro against Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum and Xanthomonas axonopodis pv. citri. Especially, compounds 7j and 7k displayed excellent antibacterial activities(100%) against the above three plant pathogenic bacteria at a concentration of 100 μg/mL. And the corresponding EC50 (50% effective concentration) values were 15.13, 30.90, 24.49 and 21.33, 24.54, 14.79 μg/mL, respectively, which were superior to the commercial antibacterial agent bismerthiazol(92.23, 58.88 and 123.02 μg/mL).

Key words: 1,3,4-Thiadiazole, Chalconesemicarbazone, Antibacterial activity