4-isopropyl-4H-1,2,4-triazole-3-thiol | 38942-52-8

• 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-isopropyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-isoprophyl-4H-1,2,4-triazole-3-thiol；4-propan-2-yl-1H-1,2,4-triazole-5-thione
• CAS: 38942-52-8
• 化学式: C₅H₉N₃S
• mdl: MFCD06654981
• 分子量: 143.213
• InChiKey: QRJRIWMZIAJIDG-UHFFFAOYSA-N

物化性质

• 沸点：
  172.3±23.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-isopropyl-4H-1,2,4-triazole-3-thiol 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-isopropyl-4H-1,2,4-triazol-3-yl)thio)ethan-1-ol
  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：

  N-(propan-2-ylcarbamothioylamino)formamide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到4-isopropyl-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