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2024 , Vol. 44 >Issue 9: 2777 - 2784

DOI: https://doi.org/10.6023/cjoc202404021

研究论文

利用碱促进环外1,3-二羰化合物的解构反应合成腙化的1,n-二羰化合物及其生物活性检测

  • 李平 ,
  • 张寅 ,
  • 杨子琪 ,
  • 郝文娟 ,
  • 姜波
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  • a 河南医学高等专科学校医学系 郑州 451191
    b 江苏师范大学化学与材料科学学院 江苏徐州 221116
†共同第一作者.

收稿日期: 2024-04-15

  修回日期: 2024-05-26

  网络出版日期: 2024-06-24

基金资助

国家自然科学基金(21971090); 河南省重点研发与推广专项(科技攻关)(212102310797); 河南省软科学研究计划(242400410409)

收起

Base-Promoted Deconstructive Reaction of Exocyclic 1,3-Dicarbonyls for Accessing Hydrazonylated 1,n-Dicarbonyls and Its Biological Evaluation

  • Ping Li ,
  • Yin Zhang ,
  • Zi-Qi Yang ,
  • Wen-Juan Hao ,
  • Bo Jiang
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  • a Medical Department, Henan Medical College, Zhengzhou 451191
    b School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
†These authors contributed equally to this work.
*E-mail: (Li, P.);
(Jiang, B.)

Received date: 2024-04-15

  Revised date: 2024-05-26

  Online published: 2024-06-24

Supported by

National Natural Science Foundation of China(21971090); Research Project on the Key R & D and Promotion Special Project (Science and Technology Research) of Henan Province(212102310797); Henan Soft Science Research Plan Project(242400410409)

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摘要

报道一类温和碱促进的环外1,3-二羰化合物、芳基重氮四氟硼酸盐和醇的三组分解构官能化反应, 使无张力环体系能直接开环, 以良好收率合成了六种不同骨架的腙化1,n-二酯衍生物(如1,6-、1,7-、1,8-和1,9-二酯)和1,n-酮酯(如1,6-和1,7-酮酯). 其中, 在形成1,n-酮酯的转化中, 该反应展现出优异(E)-选择性. 在整个有机合成过程中, 该方法具有广泛使用的潜力, 因使用了易于获得的具有不同取代形式的底物, 如环外1,3-二羰化合物和芳基重氮四氟硼酸盐, 以及温和反应条件. 对部分化合物的生物活性, 即对人肺癌细胞株MSTO-211H的抑制作用, 进行了初步检测. 结果显示化合物3c和3u展现出较为显著的抑制作用.

关键词： 解构反应; 1,n-二酯衍生物; 1,n-酮酯衍生物; 立体选择性

本文引用格式

李平 , 张寅 , 杨子琪 , 郝文娟 , 姜波 . 利用碱促进环外1,3-二羰化合物的解构反应合成腙化的1,n-二羰化合物及其生物活性检测[J]. 有机化学, 2024 , 44(9) : 2777 -2784 . DOI: 10.6023/cjoc202404021

Abstract

A mild base-promoted three-component deconstructive functionalization of exocyclic 1,3-dicarbonyls with aryl diazonium tetrafluoroborates in the presence of alcohols is reported, enabling direct ring-opening of unstrained cyclic ring systems to produce six types of skeletally diverse hydrazonylated 1,n-diesters (e.g., 1,6-, 1,7- 1,8-, and 1,9-diesters) and 1,n-ketoesters (e.g., 1,6- and 1,7-ketoesters) with good yields, and the latter demonstrated complete (E)-selectivity. The methodology has the potential to be widely used throughout organic synthesis due to the use of easily accessible substrates with different substitution patterns, such as exocyclic 1,3-carbonyls and aryl diazonium tetrafluoroborates, and mild reaction conditions. Preliminary biological evaluation of some compounds, namely their inhibitory effect on human lung cancer cell MSTO-211H, was conducted. The results showed that compounds 3c and 3w exhibited significant inhibitory effects.

Key words： deconstructive reaction; 1,n-diesters; 1,n-ketoesters; stereoselectivity

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