Citation: Wei Guangpu, Zhang Xi, Lei Qiang, Xu Miao, Zhang Mingqian, Long Yue. Synthesis and Biological Activities of Novel 1, 2, 4-Triazole Triazene Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2137-2142. doi: 10.6023/cjoc201802013 shu

Synthesis and Biological Activities of Novel 1, 2, 4-Triazole Triazene Derivatives

College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001

Corresponding author: Long Yue, longyue@zzu.edu.cn
Received Date: 7 February 2018
Revised Date: 31 March 2018
Available Online: 17 August 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. J1210060), the Science and Technology Planning Project of Henan Province (No. 0624420031) and the Basic Research Development Program of Henan Province (No. 022463001)the Science and Technology Planning Project of Henan Province 0624420031the National Natural Science Foundation of China J1210060the Basic Research Development Program of Henan Province 022463001

Figures(1)

Sixteen novel 1, 2, 4-triazole triazene derivatives were synthesized in multiple steps from the p-aminobenzoic acid. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. All the target compounds were evaluated for their anticancer activity. Among them, 2-[4-(3, 3-dimethyltriazol-1-yl)phenyl]-3-amino-4-S-(4-chlorobenzyl)-1, 2, 4-triazole (6g), 2-[4-(3, 3-dimethyltriazol-1-yl)phenyl]-3-amino-4-S-(2, 4-dichlorobenzyl)-1, 2, 4-triazole (6h), 2-[4-(3, 3-methylbenzyltriazen-1-yl)-phenyl]-3-amino-4-S-benzyl-1, 2, 4-trioxazole (6i), 2-[4-(3, 3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(4-methylbenzyl)-1, 2, 4-triazole (6j), 2-[4-(3, 3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(4-methoxybenzyl)-1, 2, 4-triazole (6l), 2-[4-(3, 3-methylbenzyltriazen-1-yl)phenyl]-3-amino-4-S-(2, 4-di-chlorobenzyl)-1, 2, 4-triazole (6p) exhibited good anti-cancer activity against J82 cells with the IC₅₀ values of 23.883, 5.512, 8.731, 8.077, 5.590 and 12.195 μmol/L, respectively. And compounds 6h, 6i, 6j, 6l exhibited good anti-cancer activity against DU145 cells with the IC₅₀ values of 13.690, 21.908, 10.772 and 4.827 μmol/L, respectively.
- triazene,
- 1, 2, 4-triazole,
- synthesis,
- antitumor
1. [1]
  Kumar, D.; Narayanam, M. K.; Chang, K. H.; Shah, K. Chem. Biol. Drug Des. 2011, 77, 182. doi: 10.1111/jpp.2011.77.issue-3
2. [2]
  Sumangala, V.; Poojary, B.; Chidananda, N.; Arulmoli, T.; Shenoy, S. Eur. J. Med. Chem. 2012, 54, 59. doi: 10.1016/j.ejmech.2012.04.024
3. [3]
  Al-Omar, M. A.; Al-Abdullah, E. S.; Shehata, I. A.; Habib, E. E.; Ibrahim, T. M.; El-Emam, A. A. Molecules 2010, 15, 2526. doi: 10.3390/molecules15042526
4. [4]
  Abdel-Wahab, B. F.; Abdel-Latif, E.; Mohamed, H. A.; Awad, G. E. A. Eur. J. Med. Chem. 2012, 52, 263. doi: 10.1016/j.ejmech.2012.03.023
5. [5]
  Li, Y. C.; Cheng, J. R.; Zheng, J. Y. Chin. J. Pestic. 1993, 32, 11 (in Chinese).
6. [6]
  Li, Y. C. Chin. J. Pestic. 1993, 32, 20 (in Chinese).
7. [7]
  Haria, M.; Bryson, H. M.; Goa, K. L. Drugs 1996, 50, 658.
8. [8]
  Casali, A.; Sega, F. M.; Casali, M.; Giuntini, T.; Cappellini, G. C.; Terzoli, E. J. Exp. Clin. Cancer Res. 2000, 19, 17.
9. [9]
  Goa, K. L.; Barradell, L. B. Drugs 1996, 51, 585. doi: 10.2165/00003495-199651040-00006
10. [10]
  Stefan, B.; Stefan, D.; Frank, L.; Nicholas, E. L.; Emma, L. S. Bioorg. Med. Chem. Lett. 2002, 12, 1849.
11. [11]
  Koji, T.; Mohammad, A. A.; Naoyuki, H.; Johan, W.; Hiroshi, S.; Yoshitsugu, S.; Hayato, F.; Satoshi, S.; Mitsuhiro, A. J. Org. Chem. 2014, 79, 6366. doi: 10.1021/jo5009838
12. [12]
  Zhang, X. H.; Chen, W. B. Asian J. Chem. 2013, 25, 9805.
13. [13]
  Chu, J.; Xie, X.-H.; Yang, S. R.; Zhan, S. Z. Inorg. Chim. Acta 2014, 410, 191. doi: 10.1016/j.ica.2013.10.026
14. [14]
  Zhu, C. S.; Chen, W. B. Asian J. Chem. 2013, 25, 7409.
15. [15]
  Sun, H.; Wang, C. M.; Yang, Y. F.; Chen. P.; Wu, Y. D.; Zhang, X. H.; Huang, Y. J. Org. Chem. 2014, 79, 11863. doi: 10.1021/jo500807d
16. [16]
  Monteiro, A. S.; Almeida, J.; Cabral, G.; Severino, P.; Videira, P. A.; Sousa, A.; Nunes, R.; Pereira, J. D.; Francisco, A. P.; Perry, M. J.; Mendes, E. Eur. J. Med. Chem. 2013, 70, 1. doi: 10.1016/j.ejmech.2013.09.040
17. [17]
  Cappoen, D.; Vajs, J.; Uythethofken, C.; Kosmrlj, J. Eur. J. Med. Chem. 2014, 77, 193. doi: 10.1016/j.ejmech.2014.02.065
18. [18]
  Rodenko, B.; Wanner, M. J.; Alkhaldi, A. A. M.; Ebiloma, G. U.; Barnes, R. L.; Kaiser, M.; Brun, R.; Mccculloch, R.; Koomen, G. J.; Koning, H. P. Antimicrob. Agents Chemother. 2015, 59, 708.
19. [19]
  Lei, Q.; Zhang, S. Y.; Liu, M. L.; Li, J.; Zhang, X.; Long, Y. Mol. Diversity 2017, 21, 957. doi: 10.1007/s11030-017-9768-1
20. [20]
  Lei, Q.; Qin, S. S.; Feng, C. N.; Li, P. P.; Zhang, X.; Long, Y. Chin. J. Org. Chem. 2016, 36, 406 (in Chinese).
21. [21]
  Yang, S. H. Chem. Intermed. 2008, (4), 20 (in Chinese). doi: 10.3969/j.issn.1672-8114.2008.04.006
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