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

doi:10.6023/cjoc202105014

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3675-3681.DOI: 10.6023/cjoc202105014 Previous Articles Next Articles

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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^,^*()

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 Shao^a, Zhijie Li^a, Yajun Wang^b, Yuyan Xiong^b(), Xiangdong Hu^a()

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.

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

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Jiyan Shao, Zhijie Li, Yajun Wang, Yuyan Xiong, Xiangdong Hu. Synthesis and Bioactivity of Tropone Derivatives as Potential Compounds against Human Gastric Cancer Cells Growth[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3675-3681.

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Fig. & Tab. 7

Figure 1. Tropone and representative natural products with tropone moiety

Scheme 1. Synthesis of tropones derivatives.

Figure 2. Crystal structure of tropones derivatives 6 and 13

Scheme 2. Synthesis of tropone derivatives 9~13

Figure 3. Effects of tropone derivatives 3, 5~13 on the cell viability of human gastric cancer cells MGC-27 (DMSO was used as negative control)

Figure 4. Growth inhibition curve of tropone derivative 9 in human gastric cancer cells MGC-27

Figure 5. Effects of compound 9 on the apoptosis of human gastric cancer cells MGC-27

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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

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

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