4-hydroxymethyl-2-(2,4,5-trimethoxyphenyl)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-hydroxymethyl-2-(2,4,5-trimethoxyphenyl)imidazole
• 英文别名: [2-(2,4,5-trimethoxyphenyl)-1H-imidazol-5-yl]methanol
• 化学式: C₁₃H₁₆N₂O₄
• 分子量: 264.281
• InChiKey: FOBCJBKGWJEZEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxymethyl-2-(2,4,5-trimethoxyphenyl)imidazole 在 氯化亚砜 作用下， 以69%的产率得到4-chloromethyl-2-(2,4,5-trimethoxyphenyl)imidazole
  参考文献：
  名称：

  Synthesis and preliminary evaluation of hydroquinone-substituted histidine derivatives as putative histaminergic neurotoxins

  摘要：

  A series of hydroquinone-substituted histidine derivatives were synthesized as potential histaminergic neurotoxins. The compounds undergo autoxidation at physiologic pH as exemplified by 2-amino-3-[2-4,5,-trihydroxyphenyl)imidazo-4-yl]propionic acid 11. One of the synthesized histidine derivatives, namely 2-amino-3-[2-(2,3-dihydroxyphenyl)imidazo-4-yl]propionic acid 8, was tested for its degenerating effect on histaminergic, dopaminergic and serotonergic neurons in rat brain. After 4 d of an unilateral injection of 1 mu l 3 mM 8 in 0.1 M phosphate buffer (pH 7.4) into the posterior hypothalamus, a decrease in immunoreactivity in the presumable histaminergic neurons was observed whilst dopaminergic and serotonergic neuronal elements were little affected. A possible mechanism of action is discussed.

  DOI：

  10.1016/0223-5234(94)90142-2
• 作为产物：
  描述：

  1,3-二羟基丙酮 、 2,4,5-trimethoxybenzamide 在 氨 、 triethyloxonium fluoroborate 作用下， 生成 4-hydroxymethyl-2-(2,4,5-trimethoxyphenyl)imidazole
  参考文献：
  名称：

  Synthesis and preliminary evaluation of hydroquinone-substituted histidine derivatives as putative histaminergic neurotoxins

  摘要：

  A series of hydroquinone-substituted histidine derivatives were synthesized as potential histaminergic neurotoxins. The compounds undergo autoxidation at physiologic pH as exemplified by 2-amino-3-[2-4,5,-trihydroxyphenyl)imidazo-4-yl]propionic acid 11. One of the synthesized histidine derivatives, namely 2-amino-3-[2-(2,3-dihydroxyphenyl)imidazo-4-yl]propionic acid 8, was tested for its degenerating effect on histaminergic, dopaminergic and serotonergic neurons in rat brain. After 4 d of an unilateral injection of 1 mu l 3 mM 8 in 0.1 M phosphate buffer (pH 7.4) into the posterior hypothalamus, a decrease in immunoreactivity in the presumable histaminergic neurons was observed whilst dopaminergic and serotonergic neuronal elements were little affected. A possible mechanism of action is discussed.

  DOI：

  10.1016/0223-5234(94)90142-2