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

doi:10.6023/cjoc202003009

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2402-2410.DOI: 10.6023/cjoc202003009 Previous Articles Next Articles

1,2,4-三唑-3-硫醚衍生物的合成、晶体结构与神经氨酸酶抑制活性

何梅^a, 贺超凡^a, 刘玲^a, 叶姣^a, 胡艾希^a, 陈云^a, 许律捷^b, 刘艾林^b

a 湖南大学化学化工学院长沙 410082;
b 中国医学科学院北京协和医学院药物研究所北京 100050

收稿日期:2020-03-05 修回日期:2020-05-21 发布日期:2020-05-29
通讯作者: 叶姣, 胡艾希 E-mail:yejiao@hnu.edu.cn;axhu@hnu.edu.cn
基金资助:
湖南省自然科学基金（No.2019JJ40030）资助项目.

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

Received:2020-03-05 Revised:2020-05-21 Published:2020-05-29
Supported by:
Project supported by the Natural Science Foundation of Hunan Province (No. 2019JJ40030).

1. cjoc202003009.pdf(1787KB)

Abstract

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.

Key words: 1,2,4-triazole-3-sulfide derivative, synthesis, crystal structure, neuraminidase inhibitory activity

Cite this article

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.

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1,2,4-三唑-3-硫醚衍生物的合成、晶体结构与神经氨酸酶抑制活性

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

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