有机化学 ›› 2021, Vol. 41 ›› Issue (9): 3675-3681.DOI: 10.6023/cjoc202105014 上一篇    下一篇

研究论文

环庚三烯酮衍生物的合成和抑制胃癌细胞增殖的活性研究

邵继炎a, 李志杰a, 王迓君b, 熊裕焱b,*(), 胡向东a,*()   

  1. a 西北大学化学与材料科学学院 合成与天然功能分子教育部重点实验室 西安 710127
    b 西北大学医学院 西部资源生物与现代生物技术教育部重点实验室 西安 710069
  • 收稿日期:2021-05-10 修回日期:2021-05-31 发布日期:2021-06-17
  • 通讯作者: 熊裕焱, 胡向东
  • 作者简介:
    † 共同第一作者.
  • 基金资助:
    国家自然科学基金(21772153); 国家自然科学基金(22071192); 陕西省科技厅基金(2019JM-151); 陕西省科技创新团队(2017KCT-37); 陕西省自然科学基金(2020JQ-611); 陕西省教育厅2020年突发公共卫生安全专项科学研究计划(20JG034); 陕西省高层次人才资助项目.

Synthesis and Bioactivity of Tropone Derivatives as Potential Compounds against Human Gastric Cancer Cells Growth

Jiyan Shaoa, Zhijie Lia, Yajun Wangb, Yuyan Xiongb(), Xiangdong Hua()   

  1. a Key Laboratory of Synthetic and National Functional Molecule Chemistry of Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127
    b Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, School of Medicine, Northwest University, Xi'an 710069
  • Received:2021-05-10 Revised:2021-05-31 Published:2021-06-17
  • Contact: Yuyan Xiong, Xiangdong Hu
  • About author:
    † (These authors contributed equally to this work).
  • Supported by:
    National Science Foundation of China(21772153); National Science Foundation of China(22071192); Science and Technology Department of Shaanxi Province(2019JM-151); Key Science and Technology Innovation Team of Shaanxi Province(2017KCT-37); Natural Science Foundation of Shaanxi Province(2020JQ-611); Special Scientific Research Plan for Emergency Public Health Safety 2020 of Shaanxi Provincial Department of Education(20JG034); High-level Talent Programs of Shaanxi Province.

基于已知的金催化氧化六元环扩环策略, 实现了一系列环庚三烯酮衍生物的合成. 发现环庚三烯酮衍生物2-羟基-3,6-二甲基-5-氧代-1,3,6-环庚三烯-1-羧酸乙酯(3)、3,6-二甲基-7-氧代-4-((三氟甲基)磺酰基)氧基)-1,3,5-环庚三烯-1-羧酸乙酯(9)、3,6-二甲基-7-氧代-4-乙烯基-1,3,5-环庚三烯-1-羧酸乙酯(10)人胃癌细胞MGC-27表现出抗增殖活性, 而活性相对较好的化合物9的抗增殖活性与胃癌细胞MGC-27凋亡没有关联.

关键词: 环庚三烯酮衍生物, 七元芳环, 胃癌, 生物活性

Based on the strategy of Au-catalyzed oxidative ring expansion of six-membered rings, the synthesis of a series of tropone derivatives was achieved. It was disclosed that tropone derivatives ethyl 2-hydroxy-3,6-dimethyl-5-oxocyclohepta- 1,3,6-triene-1-carboxylate (3), ethyl 3,6-dimethyl-7-oxo-4-(((trifluoromethyl)sulfonyl)oxy)cyclohepta-1,3,5-triene-1-carboxylate (9), and ethyl 3,6-dimethyl-7-oxo-4-vinylcyclohepta-1,3,5-triene-1-carboxylate (10) displayed antiproliferative activity against human gastric cancer cells MGC-27. Compound 9, which possesses relatively better activity, didn't show relationship between its antiproliferative activity and the apoptosis of gastric cancer cells MGC-27.

Key words: tropone, seven-membered aromatic ring, gastric cancer, bioactivity