1-(Cyclohexylthiocarbamoyl)-1,2,4-triazol | 63976-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(Cyclohexylthiocarbamoyl)-1,2,4-triazol
• 英文别名: [1,2,4]triazole-1-carbothioic acid cyclohexylamide；N-cyclohexyl-1,2,4-triazole-1-carbothioamide
• CAS: 63976-78-3
• 化学式: C₉H₁₄N₄S
• 分子量: 210.303
• InChiKey: QLEZOOJSWPRITJ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  355.5±25.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-1,2,4-三唑 、 环己基异硫氰酸脂 反应 30.0h， 以3.7%的产率得到1-(Cyclohexylthiocarbamoyl)-1,2,4-triazol
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993

文献信息

• LARSEN C.; STELION K.; HARPP D., J. ORG. CHEM., 1978, 43, NO 2, 337-339
  作者：LARSEN C.、 STELION K.、 HARPP D.

  DOI：——

  日期：——