5-氨基-1H-咪唑-4-羧酸 | 4919-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-氨基-1H-咪唑-4-羧酸
• 英文名称: 4-Amino-1H-imidazole-5-carboxylic acid
• 英文别名: 4-Amino-5-imidazolecarboxylic acid；4-amino-5-imidazole-carboxyamide；4-amino-5-imidazolecarboxylate；4-amino-5-carboxyl-imidazole；4-amino-5-carboxyimidazole
• CAS: 4919-04-4
• 化学式: C₄H₅N₃O₂
• mdl: MFCD09909757
• 分子量: 127.103
• InChiKey: PWCLNQLPYQVWAB-UHFFFAOYSA-N

物化性质

• 沸点：
  580.6±35.0 °C(Predicted)
• 密度：
  1.677±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 5-氨基-1H-咪唑-4-羧酸 在 盐酸 作用下， 生成 (9ci)-5-氨基-1H-咪唑-4-羧酸甲酯
  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