Citation: Liu Zhengfen, Zhang Chaobo, Duan Shengzu, Liu Yang, Chen Wen, Li Yan, Zhang Hongbin, Yang Xiaodong. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1506-1515. doi: 10.6023/cjoc201610043 shu

Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Indolo[b]tetrahydrofuran and Imidazolium Salts

Liu Zhengfen ^a ,
Zhang Chaobo ^a ,
Duan Shengzu ^a ,
Liu Yang ^a ,
Chen Wen ^a ,
Li Yan ^b ,
Zhang Hongbin ^a,*,, ,
Yang Xiaodong ^a,*,,

a.
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 65009
b.
State Key Laboratory for Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650204

Corresponding author: Zhang Hongbin, zhanghb@ynu.edu.cn Yang Xiaodong, xdyang@ynu.edu.cn
Received Date: 28 October 2016
Revised Date: 12 January 2017

Fund Project: the National Natural Science Foundation of China 21662043the National Natural Science Foundation of China 21332007the Program for Changjiang Scholars and Innovative Research Team in University IRT13095the Natural Science Foundation of Yunnan Province 2013FA028the National Natural Science Foundation of China 21462049the National Natural Science Foundation of China U1402227

Figures(5)

A series of novel hybrid compounds between indolo[b]tetrahydrofuran and imidazolium salts were prepared from tryptophol by four steps of Sharpless epoxidation, amidation, coupling and salt formation. Their structures were confirmed by ¹H NMR, ¹³C NMR, HRMS and X-ray crystallographic analysis. These compounds were evaluated in vitro against a panel of human tumor cell lines. The results showed that 1-((3aR, 8aS)-3, 3a-dihydro-3a-hydroxy-2H-furo[2, 3-b]indol-8(8aH)-yl)etha-none-3-(2-(naphthalen-2-yl)-2-oxoethyl)-5, 6-dimethyl-1H-benzo[d]-imidazol-3-ium bromide (20) and 1-((3aR, 8aS)-3, 3a-di-hydro-3a-hydroxy-2H-furo[2, 3-b]indol-8(8aH)-yl)ethanone-3-(2-naphthylmethyl)-5, 6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (22) exhibited higher inhibitory activity selectively against SMMC-7721, MCF-7 and SW480 cell lines compared with DDP. In particular, 1-((3aR, 8aS)-3, 3a-dihydro-3a-hydroxy-2H-furo[2, 3-b]indol-8(8aH)-yl)ethanone-3-(2-bromobenzyl)-5, 6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (24) was more selective to SW-480 cell lines with IC₅₀ values 2.0-fold lower than DDP.
- indolo[b]tetrahydrofuran,
- imidazolium salts,
- hybrid compound,
- cytotoxic activity
1. [1]
  Pan, C. X.; Guan, Y. F.; Zhang, H. B. Chin. J. Org. Chem. 2012, 32, 1116 (in Chinese).
2. [2]
  Wang, X. Q.; Li, Y.; Yang, X. D.; Zhang, H. B. Chin. J. Org. Chem. 2015, 35, 1276 (in Chinese).
3. [3]
  (a) Suzuki, T.; Choi, J. H.; Kawaguchi, T.; Yamashita, K.; Morita, A.; Hirai, H.; Nagai, K.; Hirose, T.; Omura, S.; Sunazuka, T.; Kawagishi, H. Bioorg. Med. Chem. Lett. 2012, 22, 4246.
  (b) Chaudhaery, S. S.; Roy, K. K.; Shakya, N.; Saxena, G.; Sammi, S. R.; Nazir, A.; Nath, C.; Saxena, A. K. J. Med. Chem. 2010, 53, 6490.
  (c) Luo, W.; Yu, Q. S.; Kulkarni, S. S.; Parrish, D. A.; Holloway, H. W.; Tweedie, D.; Shafferman, A.; Lahiri, D. K.; Brossi, A.; Greig, N. H. J. Med. Chem. 2006, 49, 2174.
  (d) Gavuzzo, E.; Pomponi, M. J. Biochem. Mol. Toxicol. 2002, 16, 64.
4. [4]
  (a) Hayashi, M.; Kim, Y.-P.; Takamatsu, S.; Enomoto, A.: Shinose, M.; Takahashi, Y.; Tanaka, H.; Komiyama, K.; Ohmura, S. J. Antibiot. 1996, 49, 1091.
  (b) Takamatsu, S.; Kim, Y.-P.; Enomoto, A.; Hayashi, M.; Tanaka, H.; Komiyama, K.; Ohmura, S. J. Antibiot. 1997, 50, 1069.
5. [5]
  Hayashi, M.; Rho, M.-C.; Enomoto, A.; Fukami, A.; Kim, Y.-P.; Kikuchi, Y.; Sunazuka, T.; Hirose, T.; Komiyama, K.; Ohmura, S. Proc. Natl. Acad. Sci. 2002, 99, 14728. doi: 10.1073/pnas.232562799
6. [6]
  (a) Strassmann, G.; Masui, Y.; Chizzonite, R.; Fong, M. J. Immunol. 1993, 150, 2341.
  (b) Zhang, X. G.; Bataille, R.; Jourdan, M.; Saeland, S.; Banchereau, J.; Mannoni, P.; Klein, B. Blood 1990, 76, 2599.
7. [7]
  Wan, L.; Tius, M. A. Org. Lett. 2007, 9, 647. doi: 10.1021/ol062919e
8. [8]
  (a) Vlahakis, J. Z.; Lazar, C.; Crandall, I. E.; Szarek, W. A. Bioorg. Med. Chem. 2010, 18, 6184.
  (b) Dominianni, S. J.; Yen, T. T. J. Med. Chem. 1989, 32, 2301.
  (c) Pardin, C.; Schmitzer, A. R.; Leclercq, L. Chem. Eur. J. 2010, 16, 4686.
9. [9]
  (a) Fortuna, C. G.; Barresi, V.; Berellini, G..; Musumarra, G. Bioorg. Med. Chem. 2008, 16, 4150.
  (b) Saberi, M. R.; Vinh, T. K.; Yee, S. W.; Griffiths, B. J. N.; Evan, P. J.; Simsons, C. J. Med. Chem. 2006, 49, 1016.
10. [10]
  Cui, B.; Zheng, B. L.; He, K.; Zheng, Q. Y. J. Nat. Prod. 2003, 66, 1101. doi: 10.1021/np030031i
11. [11]
  (a) Zeng, X. H.; Yang, X. D.; Zhang, Y. L.; Qing, C.; Zhang, H. B. Bioorg. Med. Chem. Lett. 2010, 20, 1844.
  (b) Yang, X. D.; Zeng, X. H.; Zhang, Y. L.; Qing, C.; Song, W. J.; Li, L.; Zhang, H. B. Bioorg. Med. Chem. Lett. 2009, 19, 1892.
12. [12]
  D'hooghe, M.; Mollet, K.; De Vreese, R.; Jonckers, T. H. M.; Dams, G.; De Kimpe, N. J. Med. Chem. 2012, 55(11), 5637.
13. [13]
  Viegas-Junior, C.; Danuello, A.; Bolzani, V. S.; Barreiro, E. J.; Fraga, C. A. M. Curr. Med. Chem. 2007, 14(17), 1829.
14. [14]
15. [15]
  (a) Zhou, B.; Liu, Z. F.; Deng, G. G.; Chen, W.; Li, M. Y.; Yang, L. J.; Li, Y.; Yang, X. D., Zhang, H. B. Org. Biomol. Chem. 2016, 14, 9423.
  (b) Zhou, Y. J.; Duan, K. Y.; Zhu, L.; Liu, Z. F.; Zhang, C. G.; Yang, L. J.; Li, M. Y.; Zhang, H. B., Yang, X. D. Bioorg. Med. Chem. Lett. 2016, 26, 460.
  (c) Liu, L. X.; Wang, X. Q.; Zhou, B.; Yang, L. J.; Li, Y.; Zhang, H. B.; Yang, X. D. Sci. Rep. 2015, 5, 13101.
  (d) Xu, X. L.; Yu, C. L.; Chen, W.; Li, Y. C.; Yang, L. J.; Li, Y.; Zhang, H. B.; Yang, X. D. Org. Biomol. Chem. 2015, 13, 1550.
  (e) Xu, X. L.; Wang, J.; Yu, C. L.; Chen, W.; Li, Y. C.; Li, Y.; Zhang, H. B.; Yang, X. D. Bioorg. Med. Chem. Lett. 2014, 24, 4926.
  (f) Sun, C. J.; Chen, W.; Li, Y.; Liu, L. X.; Wang, X. Q.; Li, L. J.; Zhang, H. B.; Yang, X. D. RSC Adv., 2014, 4, 16312.
  (g) Liu, L. X.; Wang, X. Q.; Yan, J. M.; Li, Y.; Sun, C. J.; Chen, W.; Zhou, B.; Zhang, H. B.; Yang, X. D. Eur. J. Med. Chem. 2013, 66, 423.
  (h) Wang, X. Q.; Liu, L. X.; Li, Y.; Sun, C. J.; Chen, W.; Li, L.; Zhang, H. B.; Yang, X. D. Eur. J. Med. Chem. 2013, 62, 111.
16. [16]
  Tomoyasu, H.; Toshiaki, S.; Daisuke, Y.; Naoto, K.; Tatsuya, S.; Yoshihiro, H.; Isao, K.; Satoshi, O. Tetrahedron 2005, 61, 6015. doi: 10.1016/j.tet.2005.04.056
17. [17]
  CCDC 1509927 and 1509928 contain the supplementary crystallographic data for compounds 11 and 18. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
1. [1]
  Ruihu Wang , Aidang Lu . 新型铬(VI)检测试纸的制备及应用——介绍一个应用化学综合实验. University Chemistry, 2025, 40(8): 284-290. doi: 10.12461/PKU.DXHX202410102
2. [2]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
3. [3]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
4. [4]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
5. [5]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057
6. [6]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
7. [7]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
8. [8]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
9. [9]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
10. [10]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
11. [11]
  Pengli GUAN , Renhu BAI , Xiuling SUN , Bin LIU . Trianiline-derived aggregation-induced emission luminogen probe for lipase detection and cell imaging. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1817-1826. doi: 10.11862/CJIC.20250058
12. [12]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
13. [13]
  Xiao Liu , Guangzhong Cao , Mingli Gao , Hong Wu , Hongyan Feng , Chenxiao Jiang , Tongwen Xu . Seawater Salinity Gradient Energy’s Job Application in the Field of Membranes. University Chemistry, 2024, 39(9): 279-282. doi: 10.3866/PKU.DXHX202306043
14. [14]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
15. [15]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
16. [16]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
17. [17]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
18. [18]
  Yongzhi LI , Han ZHANG , Gangding WANG , Yanwei SUI , Lei HOU , Yaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307
19. [19]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
20. [20]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

Get Citation

PDF

XML

Metrics

PDF Downloads(13)
Abstract views(1559)
HTML views(272)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142