Citation: Liu Zhengfen, Zi Yujin, Zhang Linlin, Fang Yongsheng, Shen Yanzhen, Li Yan, Yang Xiaodong, Zhang Hongbin. Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Piperonyl and Imidazolium Salts[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 669-678. doi: 10.6023/cjoc201909042 shu

Synthesis and Cytotoxic Activity of Novel Hybrid Compounds between Piperonyl and Imidazolium Salts

a.
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091
b.
State Key Laboratory for Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650204

Corresponding author: Yang Xiaodong, xdyang@ynu.edu.cn Zhang Hongbin, zhanghb@ynu.edu.cn
Received Date: 30 September 2019
Revised Date: 31 October 2019
Available Online: 13 November 2019
Fund Project: the Program for Changjiang Scholars and Innovative Research Team in University IRT17R94the National Natural Science Foundation of China 21572197the National Natural Science Foundation of China 21662043Project supported by the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT17R94), the National Natural Science Foundation of China (Nos. 21662043, 21572197, U1402227), and the Innovative Research Team (in Science and Technology) in University of Yunnan Provincethe National Natural Science Foundation of China U1402227

Figures(7)

A series of novel hybrid compounds between piperonyl and imidazolium salts were prepared from tryptophol by four steps of reduction, mesylation, 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-((benzo[d] [1, 3]dioxol-5-ylmethyl)-3-(2-naphthylmethyl))-5, 6-dimethyl-1H-benzo[d]imidazol-3-ium bromide (30) exhibited remarkable inhibitory activity selectively against HL-60, SMMC-7721, A-549, MCF-7 and SW480 cell lines compared with DDP. In particular, the compound was more selective to HL-60 cell lines with IC₅₀ values 7.2-fold lower than DDP. Further studies showed that compound 30 has the effect of inducing SMMC-7721 cell line arrest and cell apoptosis in cell cycle G0/G1.
- piperonyl,
- imidazolium salts,
- molecular hybridization,
- structure-activity relationship,
- cytotoxic activity
1. [1]
  (a) Jemal, A.; Bray, F.; Center, M. M.; Ferlay, J.; Ward, E.; Forman, D. CA Cancer J. Clin. 2011, 61, 69.
  (b) Bray, F.; Jemal, A.; Grey, N.; Ferlay, J.; Forman, D. Lancet Oncol. 2012, 13, 790.
  (c) Bray, F.; Ren, J. S.; Masuyer, E.; Ferlay, J. Int. J. Cancer 2013, 132, 1133.
2. [2]
  Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2016, 79, 629. doi: 10.1021/acs.jnatprod.5b01055
3. [3]
4. [4]
  (a) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
  (b) Soor, H. S.; Appavoo, S. D.; Yudin, A. K. Bioorg. Med. Chem. 2018, 26, 2774.
  (c) Liu, Z. F.; Li, M. Y.; Wang, B. J.; Deng, G. G.; Chen, W.; Kim, B. S.; Zhang, H. B.; Yang, X. D.; Walsh, P. J. Org. Chem. Front. 2018, 5, 1870.
  (d) Duan, S. Z.; Li, M. Y.; Ma, X. Q.; Chen, W.; Li, L.; Zhang, H. B.; Yang, X. D.; Walsh, P. J. Adv. Synth. Catal. 2018, 360, 4837.
  (e) Deng, G. G.; Li, M. Y.; Yu, K. L.; Liu, C. X.; Liu, Z. F.; Duan, S. Z.; Chen, W.; Yang, X. D.; Zhang H. B.; Walsh, P. J. Angew. Chem., Int. Ed. 2019, 58, 2826.
  (f) Yu, K. L.; Li, M. Y.; Deng, G. G.; Liu, C. X.; Wang, J.; Liu, Z. F.; Zhang, H. B.; Yang, X. D.; Walsh, P. J. Adv. Synth. Catal. 2019, 361, 4354.
5. [5]
  Gerrard, A. W. Pharm. J. 1877, 8, 214.
6. [6]
  (a) Kornienko, A.; Evidente, A. Chem. Rev. 2008, 108, 1982.
  (b) Cao, Z. F.; Yang, P.; Zhou, Q. S. Sci. China Chem. 2013, 56, 1382.
  (c) Nair, J. J.; van Staden, J.; Bastida, J. Curr. Med. Chem. 2016, 23, 161.
7. [7]
  (a) Hande, K. R. Eur. J. Cancer 1998, 34, 1514.
  (b) Damayanthi, Y.; Lown, J. W. Curr. Med. Chem. 1998, 5, 205.
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]
  Zeng, X. H.; Yang, X. D.; Zhang, Y. L.; Qing, C.; Zhang, H. B. Bioorg. Med. Chem. Lett. 2010, 20, 1844. doi: 10.1016/j.bmcl.2010.01.163
12. [12]
  Viegas, Jnr, C.; Danuello, A.; Bolzani, V. S.; Barreiro, E. J.; Fraga, C. A. M. Curr. Med. Chem. 2007, 14, 1829. doi: 10.2174/092986707781058805
13. [13]
  D^, hooghe, M.; Mollet, K.; De Vreese, R.; Jonckers, T. H. M.; Dams, G.; De Kimpe, N. J. Med. Chem. 2012, 55, 5637. doi: 10.1021/jm300383k
14. [14]
  (a) Jnr, C. V.; Danuello, A.; Bolzani, V. S.; Barreiro, E. J.; Fraga, C. A. M. Curr. Med. Chem. 2007, 14, 1829.
  (b) Walsh, J. J.; Bell, A. Curr. Pharm. Des. 2009, 15, 2970.
  (c) Sun, Y.; Sun, J.; Yan, C. G. J. Org. Chem. 2013, 9, 8.
15. [15]
16. [16]
  CCDC 1955188 contains the supplementary crystallographic data for compound 8. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/data_request/cif.
17. [17]
  Nadim, S. S.; Kathrin, J.; Matthias, B. Org. Lett. 2007, 9, 5429. doi: 10.1021/ol7021802
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