Citation: Zhang Mingqian, Liu Binkai, Lei Qiang, Yan Jingdong, Zhao Zhongyu, Long Yue. Synthesis and Biological Activities of 1, 3, 4-Thiadiazole Triazene Compound[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1064-1069. doi: 10.6023/cjoc201809003 shu

Synthesis and Biological Activities of 1, 3, 4-Thiadiazole Triazene Compound

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

Corresponding author: Long Yue, longyue@zzu.edu.cn
Received Date: 3 September 2018
Revised Date: 27 October 2018
Available Online: 21 April 2018
Fund Project: the Basic Research Development Program of Henan Province 022463001the Science and Technology Planning Project of Henan Province 0624420031Project 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 National Natural Science Foundation of China J1210060

Figures(3)

Using the splicing principle of combining the pharmacological group triazene with 1, 3, 4-thiadiazole, 15 unreported 1, 3, 4-thiadiazole triazene derivatives were synthesized. The structures of the compounds were determined by nucleated magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and high-resolution mass spectrometry (HRMS). By using the typical triazene drug dacarbazine (DTIC) and drug 5-fluorouracil (5-FU) as a reference, the activity detections of human esop-hageal cancer cells (EC109), human gastric cancer cells (MGC803), and human prostate cancer cells (PC-3) were carried out. The results showed that some compounds inhibited human gastric cancer cells (MGC803) more strongly than dacarbazine (DTIC), and the IC50 values of compounds 2-(3-methyanilino)-5-[4-(3, 3-dimethyltriazol-1-yl) phenyl]-1, 3, 4-thiadiazole (8c), 2-(2-methoxyanilino)-5-[4-(3, 3-dimethyltriazol-1-yl) phenyl]-1, 3, 4-thiadiazole (8f), and 2-(3, 4-dichloroanilino)-5-[4-(3, 3-di-methyltriazol-1-yl) phenyl]-1, 3, 4-thiadiazole (8l) were lower than those of 5-fluorouracil with 5.3, 6.5 and 6.3 μmol/L, respec-tively. Some compounds inhibited human prostate cancer cells (PC-3) more strongly than dacarbazine (DTIC), and the IC50 value of 8l is lower than that of 5-fluorouracil with 13.5 μmol/L.
- triazene,
- 1, 3, 4-thiadiazole,
- human esophageal cancer cells,
- human gastric cancer cells,
- human prostate cancer cells
1. [1]
  Nan, G. M.; Zhou, J. Chin. J. Org. Chem. 2012, 32, 1695 (in Chinese).
2. [2]
  Qiu, R. B.; Zhang, R. P.; He, L. F. Phys. Test. Chem. Anal., Part B 2015, 51, 541 (in Chinese).
3. [3]
  Li, H. F.; Lin, Q.; Kong, Y.; Li, L.; Dai, J.; Yu, W. W.; Guo, J. Tumor 2010, 30, 661 (in Chinese).
4. [4]
  Lei, Q.; Qin, S. S.; Feng, C. N.; Li, P. P.; Zhang, X.; Long, Y. Chin. J. Org. Chem. 2016, 36, 406 (in Chinese).
5. [5]
  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
6. [6]
  Carvalho, E.; Francisco, A. P.; Iley, J.; Rosa, E. Bioorg. Med. Chem. 2000, 8, 1719. doi: 10.1016/S0968-0896(00)00100-0
7. [7]
  Liu, T. T.; Wan, Y. C.; Fang, H. Chin. J. Org. Chem. 2016, 36, 417 (in Chinese).
8. [8]
  Megally Abdo, N. Y.; Kamel, M. M. Chem. Pharm. Bull. (Tokyo) 2015, 63, 369. doi: 10.1248/cpb.c15-00059
9. [9]
  Gomha, S. M.; Kheder, N. A.; Abdelaziz, M. R.; Mabkhot, Y. N.; Alhajoj, A. M. Chem. Cent. J. 2017, 11, 25. doi: 10.1186/s13065-017-0255-7
10. [10]
  Flefel, E. M.; El-Sayed, W. A.; Mohamed, A. M.; El-Sofany, W. I.; Awad, H. M. Molecules 2017, 22, 170. doi: 10.3390/molecules22010170
11. [11]
  Li, Y. J.; Yu, Y.; Jin, K.; Gao, L. X.; Luo, T. C.; Sheng, L.; Shao, X.; Li, J. Chin. J. Org. Chem. 2015, 35, 129 (in Chinese).
12. [12]
  Li, S.; Jing, F.; Fu, X. Y.; Zhao, J. J.; Wang, X. F.; Li, B. L.; Liu, Y. M.; Chen, B. Q. Chin. J. Org. Chem. 2015, 35, 2624 (in Chinese).
13. [13]
  Juszczak, M.; Matysiak, J.; Szeliga, M.; Pozarowski, P.; Niewiadomy, A.; Albrecht, J.; Rzeski, W. Bioorg. Med. Chem. Lett. 2012, 22, 5466. doi: 10.1016/j.bmcl.2012.07.036
14. [14]
  Aryanasab, F.; Halimehjani, A. Z.; Saidi, M. R. Tetrahedron Lett. 2010, 51, 790. doi: 10.1016/j.tetlet.2009.11.100
15. [15]
  Wei, G. P.; Zhang, X.; Lei, Q.; Xu, M.; Zhang, M. Q.; Long, Y. Chin. J. Org. Chem. 2018, 38, 2137 (in Chinese).
16. [16]
  Yang, H. J.; Li, Y.; Jiang, M.; Wang, J. M.; Fu, H. Chem. Eur. J. 2011, 17, 5652. doi: 10.1002/chem.v17.20
17. [17]
  Farquhar, D.; Benvenuto, J. J. Med. Chem. 1984, 27, 1723. doi: 10.1021/jm00378a033
18. [18]
  Giraldi, T.; Nisi, C. J. Med. Chem. 1977, 20, 850. doi: 10.1021/jm00216a025
19. [19]
  Feng, Y.; Zou, M. M.; Song, R. J.; Shao, X. S.; Li, Z.; Qian, X. H. J. Org. Chem. 2016, 81, 10321. doi: 10.1021/acs.joc.6b01307
20. [20]
  Yao, H. Z.; Lin, F. Y.; Chen, J. L.; Li, Y.; Cui, J. H.; Qiao, C. H. Bioorg. Med. Chem. Lett. 2016, 26, 1386. doi: 10.1016/j.bmcl.2016.01.075
21. [21]
  Rohde, J. U.; Kelley, M. R.; Lee, W. T. Inorg. Chem. 2008, 47, 11461. doi: 10.1021/ic801867r
22. [22]
  Kumavat, P. P.; Jangale, A. D.; Patil, D. R.; Dalal, K. S.; Meshram, J. S.; Dalal, D. S. Environ. Chem. Lett. 2013, 11, 177. doi: 10.1007/s10311-012-0394-y
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