5-(2,4-dichlorophenyl)-4H-1,2,4-triazol-3-amine | 168893-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,4-dichlorophenyl)-4H-1,2,4-triazol-3-amine
• 英文别名: 5-(2,4-dichlorophenyl)-1H-1,2,4-triazol-3-amine
• CAS: 168893-49-0
• 化学式: C₈H₆Cl₂N₄
• mdl: MFCD00501904
• 分子量: 229.068
• InChiKey: QJMITVPZPBGSTE-UHFFFAOYSA-N

物化性质

• 沸点：
  464.7±55.0 °C(Predicted)
• 密度：
  1.572±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  异硫氰酸甲酯 、 5-(2,4-dichlorophenyl)-4H-1,2,4-triazol-3-amine 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以35%的产率得到5-amino-3-(2,4-dichlorophenyl)-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole
  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
• 作为产物：
  描述：

  2,4-二氯苯酰肼 在 对甲苯磺酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 5-(2,4-dichlorophenyl)-4H-1,2,4-triazol-3-amine
  参考文献：
  名称：

  Design, synthesis and pharmacological evaluation of tricyclic derivatives as selective RXFP4 agonists

  摘要：

  DOI：

  10.1016/j.bioorg.2021.104782

文献信息

• Synthesis of New Fluorine Containing Triazolo- and Tetrazolopyrimidines
  作者：Arcady L. Krasovsky、Andrew M. Moiseev、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1055/s-2002-28512

  日期：——

  reaction of 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b with corresponding aminoazoles was investigated. A new simple and efficient way for the regioselective synthesis of 5-CF 3 or 7-CF 3 triazolo- and tetrazolopyrimidines is described.

  研究了 1,1,1-trifluoro-4-(sulfonyl)-but-3-ene-2,2-dioles 1a,b 与相应的氨基唑的反应。描述了一种新的简单有效的区域选择性合成 5-CF 3 或 7-CF 3 三唑并四唑嘧啶的方法。