4-(2-methyl-2-nitropropyl)-1H-imidazole

• 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-(2-methyl-2-nitropropyl)-1H-imidazole
• 英文别名: 5-(2-methyl-2-nitropropyl)-1H-imidazole
• 化学式: C₇H₁₁N₃O₂
• 分子量: 169.183
• InChiKey: DXVKCALWYADTKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-methyl-2-nitropropyl)-1H-imidazole 在 镍 氢气 作用下， 以 氨 为溶剂， 40.0 ℃ 、2.7 MPa 条件下， 反应 72.0h， 生成 1-(1H-imidazol-4-yl)-2-methyl-2-propanamine
  参考文献：
  名称：

  Synthesis and histamine H3-receptor agonist activity of mono- and dialkyl-substituted histamine derivatives

  摘要：

  In search for potential histamine H-3-receptor agonists a series of mono- and dialkyl-substituted histamine derivatives was synthesized. All target compounds were tested in vitro for their agonist activity at H-3-, H-2-, and H-1-receptors. Introduction of one ethyl or two methyl residues into histamine led to compounds with decreased histamine H-3-agonist potency in most cases. However, the non-chiral alpha,alpha-dimethylhistamine (15) was identified to be three times as active as histamine itself at H-3-receptors. In addition 15 Dimethylhistamine 23, which is a potential metabolite of (alpha R)-alpha-methylhistamine 1, proved to be inactive at all three histamine receptor subtypes.

  DOI：

  10.1016/0223-5234(96)88228-6
• 作为产物：
  描述：

  2-硝基丙烷 、 4-(氯甲基)-1H-咪唑盐酸盐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以59.5%的产率得到4-(2-methyl-2-nitropropyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis and histamine H3-receptor agonist activity of mono- and dialkyl-substituted histamine derivatives

  摘要：

  In search for potential histamine H-3-receptor agonists a series of mono- and dialkyl-substituted histamine derivatives was synthesized. All target compounds were tested in vitro for their agonist activity at H-3-, H-2-, and H-1-receptors. Introduction of one ethyl or two methyl residues into histamine led to compounds with decreased histamine H-3-agonist potency in most cases. However, the non-chiral alpha,alpha-dimethylhistamine (15) was identified to be three times as active as histamine itself at H-3-receptors. In addition 15 Dimethylhistamine 23, which is a potential metabolite of (alpha R)-alpha-methylhistamine 1, proved to be inactive at all three histamine receptor subtypes.

  DOI：

  10.1016/0223-5234(96)88228-6