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2024 , Vol. 44 >Issue 9: 2854 - 2861

DOI: https://doi.org/10.6023/cjoc202401006

研究论文

含苯并杂环芳基硫醚的合成及其抗肿瘤活性研究

  • 杨媛 ,
  • 牛丽君 ,
  • 闫泽宇 ,
  • 叶姗姗 ,
  • 张变香
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  • 山西大学化学化工学院 太原 030006

收稿日期: 2024-01-07

  修回日期: 2024-04-26

  网络出版日期: 2024-05-17

基金资助

山西省重点研发计划(202202040201009); 中央引导地方科技发展基金(YDZJSX2021C001)

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Synthesis and Antitumor Activity of Benzoheterocyclic Aryl Sulfide

  • Yuan Yang ,
  • Lijun Niu ,
  • Zeyu Yan ,
  • Shanshan Ye ,
  • Bianxiang Zhang
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  • School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006
*E-mail:

Received date: 2024-01-07

  Revised date: 2024-04-26

  Online published: 2024-05-17

Supported by

Key Research and Development Plan of Shanxi Province(202202040201009); Central Government Guides Local Science and Technology Development Fund Projects(YDZJSX2021C001)

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摘要

以2-巯基苯并唑类化合物和环状二芳基碘鎓盐为原料, 在CuI的催化下成功合成了含苯并杂环的芳硫醚类化合物. 采用1H NMR、13C NMR、紫外可见光谱等技术对目标产物进行了表征. 探究了反应的最佳条件, 生成物最高产率达到了95%. 同时, 对产物进行了抗肿瘤等生理活性测试, 产物表现出良好的抗肿瘤活性. 与线性的二芳基碘鎓盐相比, 反应中生成的碘苯副产物被有效地固定在生成物中, 提高了反应的原子经济性. 此外, 分子结构中的C—I键为后续反应或者应用提供了明确的反应位点.

关键词： 2-巯基苯并唑类; 环状二芳基碘鎓盐; 芳基硫醚; 苯并杂环

本文引用格式

杨媛 , 牛丽君 , 闫泽宇 , 叶姗姗 , 张变香 . 含苯并杂环芳基硫醚的合成及其抗肿瘤活性研究[J]. 有机化学, 2024 , 44(9) : 2854 -2861 . DOI: 10.6023/cjoc202401006

Abstract

Aryl thioethers containing benzene heterocycles were synthesized from reaction of 2-mercaptobenzazoles with cyclic diaryl iodonium salts by CuI catalyst. The target products were characterized by 1H NMR, 13C NMR and UV-Vis spectroscopies. The optimum reaction conditions were discussed, and the highest yield of the target product reached 95%. The optical properties and physiological activities of the products were also tested and analyzed. At the same time, anti-tumor activity tests were conducted on the products, and some products showed good anti-tumor activity. Compared with linear diaryliodonium salts, the iodobenzene by-product generated in the reaction is immobilized in the product, which improves the atom economy, and the C—I bond in the molecular structure provides a reaction site for subsequent reactions or applications.

Key words： 2-mercaptobenzazoles; cyclic diaryl iodonium salts; arylsulfide; benzohybrid ring

参考文献

[1]
Abedinifar, F.; Bahadorikhalili, S.; Larijani, B. Appl. Organomet. Chem. 2022, 36, 6482.
[2]
Chen, L.; Noory Fajer, A.; Yessimbekov, Z.; Kazemi, M.; Mohammadi, M. J. Sulphur. Chem. 2019, 40, 468.
[3]
Isshiki, R.; Kurosawa, M. B.; Muto, K.; Yamaguchi, J. J. Am. Chem. Soc. 2021, 143, 10333.
[4]
Vessally, E.; Didehban, K.; Mohammadi, R.; Hosseinian, A.; Babazadeh, M. J. Sulphur. Chem. 2018, 39, 332.
[5]
Liu, G.; Huth, J. R.; Olejniczak, E. T.; Mendoza, R.; DeVries, P.; Leitza, S.; Reilly, E. B.; Okasinski, G. F.; Fesik, S. W.; von Geldern, T. W. J. Med. Chem. 2001, 44, 1202.
[6]
Liu, L.; Stelmach, J. E.; Natarajan, S. R.; Chen, M.-H.; Singh, S. B.; Schwartz, C. D.; Fitzgerald, C. E.; O'Keefe, S. J.; Zaller, D. M.; Schmatz, D. M. Bioorg. Med. Chem. Lett. 2003, 13, 3979.
[7]
Li, W.; Wang, H.; Liu, S.; Feng, H.; Benassi, E.; Qian, B. Adv. Synth. Catal. 2020, 362, 2666.
[8]
Yang, S.; Li, L.; Zhao, J. Adv. Synth. Catal. 2022, 364, 4166.
[9]
Li, Z.-H.; Liu, X.-Q.; Zhao, T.-Q.; Geng, P.-F.; Liu, Y.; Zhao, B.; Guo, W.-G.; Yu, B.; Liu, H.-M. Bioorg. Med. Chem. Lett. 2017, 27, 4377.
[10]
Yan, L.; Liang, J.; Yao, C.; Wu, P.; Zeng, X.; Cheng, K.; Yin, H. ChemMedChem 2016, 11, 822.
[11]
Ye, J.; Liu, Y.; Luo, J. Org. Lett. 2023, 25, 8451.
[12]
Liu, J.; Wan, J. P.; Liu, Y. Org. Chem. Front. 2024, 11, 597.
[13]
Wu, Z. H.; Luo, J. W. Chin. J. Org. Chem. 2022, 42, 3721 (in Chinese)
[13]
(吴豪志, 罗姜万, 有机化学, 2022, 42, 3721.)
[14]
Kang, M. S.; Xin, J. Y.; Jia, Z. Green Synth. Catal. 2022, 3, 309.
[15]
Kesavan, A.; Sahu, A. K.; Anbarasan, P. Org. Lett. 2023, 25, 4765.
[16]
Kanchana, U.; Diana, E. J.; Mathew, T. V. Asian J. Org. Chem. 2022, 11, e202200038.
[17]
Qin, Y.; Sun, R.; Gianoulis, N. P.; Nocera, D. G. J. Am. Chem. Soc. 2021, 143, 2005.
[18]
Sundaravelu, N.; Sangeetha, S.; Sekar, G. Chem. Commun. 2021, 19, 1459.
[19]
Uchikura, T.; Hara, Y.; Tsubono, K.; Akiyama, T. ACS Org. Inorg. Au 2021, 1, 23.
[20]
Kumar, Y.; Ila, H. Org. Lett. 2021, 23, 1698.
[21]
Sangeetha, S.; Sekar, G. Chem. Commun. 2020, 56, 10906.
[22]
Singla, D.; Luxami, V.; Paul, K. Org. Chem. Front. 2023, 10, 237.
[23]
Postnikov, P. S.; Guselnikova, O. A.; Yusubov, M. S.; Yoshimura, A.; Nemykin, V. N.; Zhdankin, V. V. J. Org. Chem. 2015, 80, 5783.
[24]
Zhu, D.; Liu, Q.; Luo, B.; Chen, M.; Pi, R.; Huang, P.; Wen, S. Adv. Synth. Catal. 2013, 355, 2172.
[25]
Liu, L.; Qiang, J.; Bai, S.; Li, Y.; Li, J. Appl. Organomet. Chem. 2017, 31, e3810.
[26]
Hou, M.; Deng, R.; Gu, Z. Org. Lett. 2018, 20, 5779.
[27]
Zhang, B. X.; Wu, Q.; Chao, J. B.; Guo, Y. L. Chin. J. Synth. Chem. 2013, 21, 86 (in Chinese).
[27]
(张变香, 吴群, 钞建宾, 郭一力, 合成化学, 2013, 21, 86.)
[28]
Shimizu, M.; Ogawa, M.; Tamagawa, T.; Shigitani, R.; Nakatani, M.; Nakano, Y. Eur. J. Org. Chem. 2016, 2016, 2785.
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