4-(4-(dimethylamino)phenyl)-4H-1,2,4-triazole-3-thiol | 642462-59-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-(dimethylamino)phenyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-[4-(Dimethylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione；4-[4-(dimethylamino)phenyl]-1H-1,2,4-triazole-5-thione
• CAS: 642462-59-7
• 化学式: C₁₀H₁₂N₄S
• 分子量: 220.298
• InChiKey: GFVDUPMVOCZPFO-UHFFFAOYSA-N

物化性质

• 沸点：
  348.0±44.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1-(2,3-二氢-1,4-苯并二氧)乙酮 、 4-(4-(dimethylamino)phenyl)-4H-1,2,4-triazole-3-thiol 以 乙醇 为溶剂， 以65%的产率得到1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-(4-(dimethylamino)phenyl)-4H-1,2,4-triazol-3-yl)thio)ethan-1-one
  参考文献：
  名称：

  Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

  摘要：

  Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo [b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 mu M-13.6 mu M. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112218
• 作为产物：
  描述：

  4-二甲氨基苯基硫代异氰酸酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-(4-(dimethylamino)phenyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Structure-activity relationships of triazole-benzodioxine inhibitors of cathepsin X

  摘要：

  Cathepsin X is a cysteine carboxypeptidase that is involved in various physiological and pathological processes. In particular, highly elevated expression and activity of cathepsin X has been observed in cancers and neurodegenerative diseases. Previously, we identified compound Z9 (1-(2,3-dihydrobenzo [b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-one) as a potent and specific reversible cathepsin X inhibitor. Here, we have explored the effects of chemical variations to Z9 of either benzodioxine or triazol moieties, and the importance of the central ketomethylenethio linker. The ketomethylenethio linker was crucial for cathepsin X inhibition, whereas changes of the triazole heterocycle did not alter the inhibitory potencies to a greater extent. Replacement of benzodioxine moiety with substituted benzenes reduced cathepsin X inhibition. Overall, several synthesized compounds showed similar or improved inhibitory potencies against cathepsin X compared to Z9, with IC50 values of 7.1 mu M-13.6 mu M. Additionally, 25 inhibited prostate cancer cell migration by 21%, which is under the control of cathepsin X. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112218