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
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