Citation: He Mei, He Chaofan, Liu Ling, Ye Jiao, Hu Aixi, Chen Yun, Xu Lujie, Liu Ailin. Synthesis, Crystal Structure and Neuraminidase Inhibitory Activity of 1, 2, 4-Triazole-3-sulfide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2402-2410. doi: 10.6023/cjoc202003009 shu

Synthesis, Crystal Structure and Neuraminidase Inhibitory Activity of 1, 2, 4-Triazole-3-sulfide Derivatives

He Mei ^a ,
He Chaofan ^a ,
Liu Ling ^a ,
Ye Jiao ^a,, ,
Hu Aixi ^a,, ,
Chen Yun ^a ,
Xu Lujie ^b ,
Liu Ailin ^b

a.
College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082
b.
Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050

Corresponding author: Ye Jiao, yejiao@hnu.edu.cn Hu Aixi, axhu@hnu.edu.cn
Received Date: 5 March 2020
Revised Date: 21 May 2020
Available Online: 27 May 2020
Fund Project: Natural Science Foundation of Hunan Province 2019JJ40030Project supported by the Natural Science Foundation of Hunan Province (No. 2019JJ40030)

Figures(7)

A series of 1, 2, 4-triazole-3-sulfide derivatives were designed and synthesized. Their chemical structures were confirmed by ¹H NMR, ¹³C NMR, MS and elemental analysis. The crystal structure of (E)-4-(4-hydroxy-3-methoxyphenyl-methyleneamino)-5-ethyl-4H-1, 2, 4-triazole-3-propylsulfide (1c) was determined by X-ray diffraction analysis. The preliminary assay of neuraminidase (NA, H1N1) inhibitory activity in vitro showed that most of compound 1 has more potent NA inhibitory activity. Among them, compounds (E)-4-(4-hydroxy-3-methoxyphenyl-methyleneamino)-5-ethyl-4H-1, 2, 4-triazole-3-ethylsulfide (1b) and 1c showed the best inhibitory activity with IC₅₀ values of (6.86±2.08) and (9.1±1.56) μg/mL, respectively.
- 1, 2, 4-triazole-3-sulfide derivative,
- synthesis,
- crystal structure,
- neuraminidase inhibitory activity
1. [1]
  Williams, S.; Fitzner, J.; Merianos, A. Bull. W. H. O. 2014, 92, 60. doi: 10.2471/BLT.12.116723
2. [2]
  Kobasa, D.; Jones, S. M.; Shinya, K. Nature 2016, 445, 319.
3. [3]
  Wang, P. C; Fang, J. M.; Tsai, K. C. J. Med. Chem. 2016, 59, 5297. doi: 10.1021/acs.jmedchem.6b00029
4. [4]
  Kakuta, M.; Kubo, S.; Tanaka, M. Antiviral Res. 2013, 100, 190. doi: 10.1016/j.antiviral.2013.08.004
5. [5]
  Leang, S. K.; Kwok, S.; Sullivan, S. G. Influenza Other Respir. Viruses 2014, 8, 135. doi: 10.1111/irv.12187
6. [6]
  Harrington, P. J.; Brown, J. D.; Foderaro, T. Org. Process Res. Dev. 2003, 8, 86.
7. [7]
  Zhao, X.; Jie, Y.; Rosenberg, M. Antiviral Res. 2012, 96, 91. doi: 10.1016/j.antiviral.2012.09.001
8. [8]
  LackenAy, A.; Aesselaar, T. G.; Daniels, R. S. Antiviral Res. 2018, 157, 38. doi: 10.1016/j.antiviral.2018.07.001
9. [9]
  Air, G. M. Influenza Other Respir. Viruses 2012, 6, 245. doi: 10.1111/j.1750-2659.2011.00304.x
10. [10]
  Tong, S.; Li, Y.; Rivailler, P.; Conrardy, C.; Alvarez Castillo, D. A.; Chen, L. M.; Recuenco, S.; Ellison, J. A.; Davis, C. T.; York, I. A.; Turmelle, A. S.; Moran, D.; Rogers, S.; Shi, M.; Tao, Y.; Weil, M. R.; Tang, K.; Rowe, L. A.; Sammons, S.; Xu, X.; Frace, M.; Lindblade, K. A.; Cox, N. J.; Anderson, L. J.; Rupprecht, C. E.; Donis, R. O. Proc. Natl. Acad. Sci. U. S. A. 2012, 109, 4269. doi: 10.1073/pnas.1116200109
11. [11]
  Wang, K.; Fei, Y.; Wang, L. Eur. J. Med. Chem. 2017, 141, 648. doi: 10.1016/j.ejmech.2017.10.004
12. [12]
  Pires, C. D. M.; Drusano, G. L.; Adams, J. R. Eur. J. Pharm. Sci. 2018, 111, 443. doi: 10.1016/j.ejps.2017.10.027
13. [13]
  Dai, X. Q.; Zhu, Y. B.; Wang, Z. Y.; Weng, J. Q. Chin. J. Org. Chem. 2017, 37, 1924(in Chinese).
14. [14]
  Shen, Z. H.; Sun, Z. H.; Becnel, J. J.; Estep, A.; Wedge, D. E.; Tan, C. X.; Weng, J. Q.; Han, L.; Liu, X. H. Lett. Drug Des. Discovery 2018, 15, 951. doi: 10.2174/1570180815666180102141640
15. [15]
  Chen, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng. W. L.; Liu, X. H. J. Heterocycl. Chem. 2018, 55, 946. doi: 10.1002/jhet.3123
16. [16]
  Zhai, Z. W.; Wang, Q.; Shen, Z. H.; Tan, C. X.; Weng, J. Q.; Liu, X. H. Chin. J. Org. Chem. 2017, 37, 232(in Chinese).
17. [17]
  Liu, X. H.; Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L. Eur. J. Med. Chem. 2017, 125, 881. doi: 10.1016/j.ejmech.2016.10.017
18. [18]
  Li, Q. M.; Pang, K. S.; Zhao, J. P.; Liu, X. H.; Weng, J. Q. Chin. J. Org. Chem. 2017, 37, 1009(in Chinese).
19. [19]
  Shi, J. J.; Ren, G. H.; Dai, Z. M.; Wu, N, J.; Weng, J. Q.; Xu, T. M.; Liu, X. H.; Tan, C. X. Lett. Drug Des. Discovery 2018, 15, 15. doi: 10.2174/1570180814666170505123102
20. [20]
  Wang, Y. R.; Zheng, D. D.; Wang, Y.; Ye, H.; Yao, W.; Ding, Y. Chin. J. Org. Chem. 2019, 39, 2053(in Chinese).
21. [21]
  Ezabadia, I. R.; Camoutsisa, C.; Zoumpoulakisb, P.; Geronikakic, A.; Sokovićd, M.; Glamočilijad, J.; Ćirićd, A. Bioorg. Med. Chem. 2008, 16, 1150. doi: 10.1016/j.bmc.2007.10.082
22. [22]
  Pardeshi, S.; Bobade, V. D. Bioorg. Med. Chem. Lett. 2011, 21, 6559. doi: 10.1016/j.bmcl.2011.08.049
23. [23]
  Upmanyu, N.; Gupta, J. K.; Shah, K. J. Pharm. BioAllied Sci. 2011.
24. [24]
  Liu, X. H.; Pan, L.; Weng, J. Q. Mol. Diversity 2012, 16, 251. doi: 10.1007/s11030-011-9352-z
25. [25]
  Abou-Seri, S. M. Eur. J. Med. Chem. 2010, 45, 4113. doi: 10.1016/j.ejmech.2010.05.072
26. [26]
  Sharma, V.; Mehta, D. K.; Das, R.; Kaur, P. K. Int. J. Pharm. Pharm. Sci. 2016, 8, 28.
27. [27]
  Liu, X.; Clercq, E. D.; Aalzarini, J. Lett. Drug Des. Discovery 2013, 10, 27. doi: 10.2174/157018013804142429
28. [28]
  Kamel, M. M.; Megally, N. Y. Eur. J. Med. Chem. 2014, 86, 75. doi: 10.1016/j.ejmech.2014.08.047
29. [29]
  El-Husseiny, W. M.; El-Sayed, M. A.-A.; Abdel-Aziz, N. I.; El-Azab, A. S.; Asirig, Y. A. Eur. J. Med. Chem. 2018, 158, 134. doi: 10.1016/j.ejmech.2018.09.007
30. [30]
  Liu, L.; Ye, J.; Xiao, M. W.; Yuan, K. Y; He, M.; Hu, A. X. J. Heterocycl. Chem. 2019, 56, 2192. doi: 10.1002/jhet.3612
31. [31]
  Yang, Q. C.; Sun, X. H.; Liu, Y. F. Chin. J. Struct. Chem. 2015, 34, 197.
32. [32]
  Sheldrick, G. M. SADABS, Program for Empirical Absorption Correction of Area Detector Data, University of Gotingen, Germany, 1996.
33. [33]
  Sheldrick, G. M. SHELXTL V5.1, Software Reference Manual, Brucker AXS, Inc., Madision, Wisconsin, USA, 1997.
34. [34]
  Wang, X. F. M.S. Thesis, Nankai University, Tianjin, 2014 (in Chinese).
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