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2021 , Vol. 41 >Issue 9: 3539 - 3549

DOI: https://doi.org/10.6023/cjoc202101029

研究论文

作为杀菌和杀虫先导的1,2,4-噁二嗪衍生物的设计与合成研究

  • 章乐天 ,
  • 苏嘉媛 ,
  • 徐晓勇
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  • 华东理工大学药学院 上海市化学生物学(芳香杂环)重点实验室 上海 200237

收稿日期: 2021-01-18

  修回日期: 2021-03-26

  网络出版日期: 2021-06-07

基金资助

国家自然科学基金(21672061); 国家重点研发计划(2017YFD0200505); 上海市教委创新计划(201701070002E00037)

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Design and Synthesis of 1,2,4-Oxadiazine Derivatives as Promising Fungicide and Insecticide Lead Compound

  • Letian Zhang ,
  • Jiayuan Su ,
  • Xiaoyong Xu
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  • Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237
* Corresponding author. E-mail:

Received date: 2021-01-18

  Revised date: 2021-03-26

  Online published: 2021-06-07

Supported by

National Natural Science Foundation of China(21672061); National Key Research Program of China(2017YFD0200505); Innovation Program of Shanghai Municipal Education Commission(201701070002E00037)

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摘要

噁二嗪片段常用于小分子的修饰和构象限制, 同时噁二嗪也是一种理想的酰胺电子等排体. 基于商品化琥珀酸脱氢酶抑制剂杀菌剂的结构框架, 通过生物电子等排手段, 以噁二嗪替换酰胺结构, 设计并合成了24个1,2,4-噁二嗪类化合物. 生物活性测试结果表明, 在400 mg/L浓度下, 大部分化合物对黄瓜霜霉病表现出较好的活性. 此外, 在600 mg/L的浓度下, 这些化合物对粘虫的致死率达到100%, 说明噁二嗪的结构值得作为先导继续研究, 进而发现活性优异的新化合物.

关键词： 噁二嗪; 合成; 生物电子等排; 生物活性

本文引用格式

章乐天 , 苏嘉媛 , 徐晓勇 . 作为杀菌和杀虫先导的1,2,4-噁二嗪衍生物的设计与合成研究[J]. 有机化学, 2021 , 41(9) : 3539 -3549 . DOI: 10.6023/cjoc202101029

Abstract

Oxadiazine is an active fragment and usually is used for modification and conformation restriction of small molecules, meanwhile, it can be considered as an ideal and completely competent surrogate for the amide group. Based on the general framework of marketed succinate dehydrogenase inhibitors, twenty-four 1,2,4-oxadiazine compounds were designed and synthesized. The bioactivity test results showed that most of compounds exhibited good activities against Pseudoperonospora cubensis at 400 mg/L. In addition, the oxadiazine compounds have a 100% mortality against armyworms at 600 mg/L, which illustrates that oxadiazine structure is worth to be a lead compound and further modification to discover novel active with practical potentials.

Key words： oxadiazine; synthesis; bioisosterism; biological activities

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