4-(3-Allyloxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester | 691356-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-Allyloxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester
• CAS: 691356-84-0
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: LUXQFUIOQIBFOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  53.35
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(3-Allyloxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester 在 碘 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以0.40 g的产率得到4-[3-(2,3-Bis-nitrooxy-propoxy)-propyl]-1H-imidazole
  参考文献：
  名称：

  A new class of NO-donor H3-antagonists

  摘要：

  Synthesis and pharmacological characterisation of a series of compounds obtained by joining, through appropriate spacers, NO-donor furoxan and nitrooxy moieties to the imidazole ring, as well as their structurally related analogues devoid of NO-donating properties are described. All the products were studied for their capacity to interact with H3-receptors present on the guinea-pig ileum and with H2-receptors present on guinea-pig right atrium. The whole series of products displayed reversible H3-antagonistic activity. No activity on H2-receptors was observed when the products were tested at 10 microM concentration. Many of the products were also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of their H3-antagonism. This phenomenon seems to be dependent on various factors; for some compounds it proved to be dependent on NO-mediated sGC activation, for other products it could be due to their weak M3-antagonism. The investigation of the lipophilic-hydrophilic balance of all the products indicates, for many of them, an ideal value to cross the blood-brain barrier.

  DOI：

  10.1016/j.farmac.2003.12.008
• 作为产物：
  描述：

  4-(3-Allyloxy-propyl)-1-trityl-1H-imidazole 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 4-(3-Allyloxy-propyl)-imidazole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A new class of NO-donor H3-antagonists

  摘要：

  Synthesis and pharmacological characterisation of a series of compounds obtained by joining, through appropriate spacers, NO-donor furoxan and nitrooxy moieties to the imidazole ring, as well as their structurally related analogues devoid of NO-donating properties are described. All the products were studied for their capacity to interact with H3-receptors present on the guinea-pig ileum and with H2-receptors present on guinea-pig right atrium. The whole series of products displayed reversible H3-antagonistic activity. No activity on H2-receptors was observed when the products were tested at 10 microM concentration. Many of the products were also able to induce partial relaxation when added to the bath after electrical contraction of the guinea-pig ileum during the study of their H3-antagonism. This phenomenon seems to be dependent on various factors; for some compounds it proved to be dependent on NO-mediated sGC activation, for other products it could be due to their weak M3-antagonism. The investigation of the lipophilic-hydrophilic balance of all the products indicates, for many of them, an ideal value to cross the blood-brain barrier.

  DOI：

  10.1016/j.farmac.2003.12.008