N-乙酰基苯并噁唑啉酮及金属配合物的合成、生物活性和分子对接研究

doi:10.19640/j.cnki.jtau.2019.01.016

天津农学院学报 ›› 2019, Vol. 26 ›› Issue (1): 69-73.doi: 10.19640/j.cnki.jtau.2019.01.016

N-乙酰基苯并噁唑啉酮及金属配合物的合成、生物活性和分子对接研究

杨丹, 罗富璀, 杨颖婷, 刘闯, 朱华玲^通信作者, 吕丽娟

天津农学院基础科学学院,天津 300384

收稿日期:2018-05-07 出版日期:2019-03-20 发布日期:2019-10-09
通讯作者: 刘黎瑶（1988-）,女,讲师,博士,主要从事药物制剂方面的研究。E-mail:llymeilin@163.com。
作者简介:刘彤（1996-）,女,本科在读,主要从事药物制剂方面的研究。E-mail: 1250222636@qq.com。
基金资助:
天津市教委科研计划项目（2017KJ181）; 天津市水产产业技术体系创新团队项目（ITTFRS2017004）; 国家自然科学基金面上项目（31170442）

Synthesis, biological activity and molecular docking of N-acetyl benzoxazolinone and its metal complexes

YANG Dan, LUO Fu-cui, YANG Ying-ting, LIU Chuang, ZHU Hua-ling^{Corresponding Author}, LÜ Li-juan

College of Basic Science, Tianjin Agricultural University, Tianjin 300384, China

Received:2018-05-07 Online:2019-03-20 Published:2019-10-09

摘要/Abstract

摘要： 苯并噁唑啉酮类化合物具有杀虫、杀菌、除草、植物生长调节、异株克生以及消炎等广泛生物活性,在植物自我防御中起着重要作用。为寻找新型活性化合物,合成了乙酰基苯并噁唑酮及其铜、镍和锌配合物,对合成的配合物进行了红外、紫外等结构表征,除草、抑菌活性测试和分子对接研究。试验结果表明,乙酰基苯并噁唑啉酮的铜配合物具有明显的抑制大肠杆菌和枯草芽孢杆菌的能力,有望开发成广谱抗菌药。3种配合物对小麦、油菜和稗草都有明显的抑制能力,特别是对油菜根的抑制能力尤为突出,接近100%,有开发成除草剂的潜在优势。分子对接的结果表明,3种配合物与原卟啉原氧化酶的对接能较低,抑制常数较小,3种配合物可能是通过抑制原卟啉原氧化酶的活性而表现出除草活性的。

关键词: 苯并噁唑酮, 配合物, 生物活性, 分子对接

Abstract: Benzoxazolinone derivatives have an important role in the self defense of plants, such as insecticidal, bactericidal, weed killing, plant growth regulation, hetero bioactivity and anti-inflammatory activity. In order to find new active compounds, Acetyl-benzoxazolinone and its copper, nickel and zinc complexes were synthesized. The IR and UV characterization, herbicidal, anti-bacterial activities and molecular docking of the synthetic complexes were carried out. The experimental results show that the copper complex of acetyl benzoxazolinone has the ability to inhibit Escherichia coli and Bacillus Subtilis, and is expected to be developed to be a broad-spectrum antimicrobial agent. The three complexes have obvious inhibition ability to wheat, rape and barnyard grass, especially the inhibition rate to rape root, close to 100%, which suggest that they have the potential advantage of developing herbicide. The results of molecular docking show that the docking energy of the three complexes with protoporphyrinogen oxidase is low and the inhibition constant is small. The three complexes show herbicidal activity probably by inhibiting the activity of protoporphyrinogen oxidase.

Key words: benzoxazolinone, complexes, biological activity, molecular docking

中图分类号:

O621.1

杨丹, 罗富璀, 杨颖婷, 刘闯, 朱华玲, 吕丽娟. N-乙酰基苯并噁唑啉酮及金属配合物的合成、生物活性和分子对接研究[J]. 天津农学院学报, 2019, 26(1): 69-73.

YANG Dan, LUO Fu-cui, YANG Ying-ting, LIU Chuang, ZHU Hua-ling, LÜ Li-juan. Synthesis, biological activity and molecular docking of N-acetyl benzoxazolinone and its metal complexes[J]. Journal of Tianjin Agricultural University, 2019, 26(1): 69-73.

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http://xuebao.tjau.edu.cn/CN/Y2019/V26/I1/69

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N-乙酰基苯并噁唑啉酮及金属配合物的合成、生物活性和分子对接研究

Synthesis, biological activity and molecular docking of N-acetyl benzoxazolinone and its metal complexes

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