高等学校化学学报 ›› 2018, Vol. 39 ›› Issue (7): 1455.doi: 10.7503/cjcu20170785

• 有机化学 • 上一篇    下一篇

含苯并三嗪酮的1,4-戊二烯-3-酮衍生物的合成及抑菌活性

张菊平, 李普, 王一会, 张橙, 陈丽娟, 汤旭, 贺鸣, 薛伟()   

  1. 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
  • 收稿日期:2017-12-01 出版日期:2018-07-10 发布日期:2018-04-17
  • 作者简介:联系人简介: 薛 伟, 男, 博士, 教授, 博士生导师, 主要从事新农药和医药的创制研究. E-mail: wxue@gzu.edu.cn
  • 基金资助:
    国家重点研发计划项目(批准号: 2017YFD0200506)、 国家自然科学基金(批准号: 21462012)、 贵州省优秀青年科技人才培养对象专项(批准号: 黔科合人字(2015)35号)和贵州大学研究生创新基金项目(批准号: 2017060)资助.

Synthesis and Antibacterial Activities of Penta-1,4-dien-3-one Derivatives Containing a Benzotriazin-4(3H)-one Moiety

ZHANG Juping, LI Pu, WANG Yihui, ZHANG Cheng, CHEN Lijuan, TANG Xu, HE Ming, XUE Wei*()   

  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 and Development of Fine Chemicals, Guizhou University, Guiyang 550025, China
  • Received:2017-12-01 Online:2018-07-10 Published:2018-04-17
  • Contact: XUE Wei E-mail:wxue@gzu.edu.cn
  • Supported by:
    † Supported by the National Key Research and Development Program of China(No. 2017YFD0200506), the National Natural Science Foundation of China(No. 21462012), the Special Fund for Outstanding Scientific and Technological Candidates of Guizhou Province, China(No.201535) and the Innovation Fund for Graduate Student of Guizhou University, China(No.2017060).

摘要:

为了得到生物活性较好的姜黄素衍生物, 通过1-苯基-5-取代基-1,4-戊二烯-3-酮和3-氯甲基苯并三嗪酮反应, 合成了14个含苯并三嗪酮的1,4-戊二烯-3-酮衍生物; 采用核磁共振波谱(NMR)和高分辨质谱(HRMS)对化合物的结构进行了表征. 初步的生物活性测试结果表明, 部分化合物显示出较好的抑菌活性, 在100 μg/mL剂量下, 化合物6b, 6j和6l对柑橘溃疡病菌(Xac)的抑制率分别为68.8%, 71.0%和100%; 化合物6a, 6d, 6h和6i对烟草青枯病菌(R. solanacearum)的抑制率分别为51.8%, 53.0%, 50.7%和76.9%. 此外, 化合物6l和6i对柑橘溃疡病菌和烟草青枯病菌的半最大效应浓度(EC50)值分别为27.44和48.77 μg/mL, 优于对照药剂噻菌铜(51.35和87.26 μg/mL), 有望成为柑橘溃疡病菌和烟草青枯病菌的抑制剂.

关键词: 1, 4-戊二烯-3-酮, 苯并三嗪酮, 抑菌

Abstract:

To find novel curcumin derivatives with potent biological activities, fourteen new penta-1,4-dien-3-one derivatives containing benzotriazin-4(3H)-one moiety were synthesized by multistep synthetic procedures with two key intermediates penta-1,4-dien-3-one and 3-(chloromethyl)benzo[1,2,3]triazin-4(3H)-one. The structures of target compounds 6 were confirmed by means of nuclear magnetic resonance(NMR), and high resolution mass spectrometer(HRMS). The bioassay data showed that some compounds exhibited good antibacterial activities at the dosage of 100 μg/mL and 50 μg/mL against Xanthomonas axonopodis pv. Citri(Xac) and Ralstonia solanacearum(R. solanacearum). Moreover, compounds 6b, 6j and 6l had 68.8%, 71.0% and 100% antibacterial activity against Xac at 100 μg/mL. Compounds 6a, 6d, 6h and 6i showed 51.8%, 53.0%, 50.7 and 76.9% antibacterial activity against R. solanacearum at 100 μg/mL. Meanwhile, all target compounds displayed excellent antibacterial activity against R. solanacearum at 50 μg/mL, which were superior to that of thiodiazole copper. In addition, compounds 6l and 6i showed wonderful inhibitory activities against Xac and R. solanacearum with the EC50 values of 27.44 and 48.77 μg/mL, respectively. which were better than those of thiodiazole copper(51.35 μg/mL and 87.26 μg/mL, respectively). Those two penta-1,4-dien-3-one derivatives could be considered as useful templates for future development to obtain more potent antibacterial agents.

Key words: Penta-1, 4-dien-3-one, Benzotriazin-4(3H)-one, Antibacterial

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