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   

  1. 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 出版日期:2020-08-25 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 Meia, He Chaofana, Liu Linga, Ye Jiaoa, Hu Aixia, Chen Yuna, Xu Lujieb, Liu Ailinb   

  1. 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 Online:2020-08-25 Published:2020-05-29
  • Supported by:
    Project supported by the Natural Science Foundation of Hunan Province (No. 2019JJ40030).

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