N-[2-(1H-Imidazol-4-yl)-ethyl]-2-phenoxy-acetamide | 160208-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[2-(1H-Imidazol-4-yl)-ethyl]-2-phenoxy-acetamide
• 英文别名: N-[2-(1H-imidazol-5-yl)ethyl]-2-phenoxyacetamide
• CAS: 160208-19-5
• 化学式: C₁₃H₁₅N₃O₂
• mdl: MFCD07639150
• 分子量: 245.281
• InChiKey: DYQCQBZPYVZWBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(1H-Imidazol-4-yl)-ethyl]-2-phenoxy-acetamide 在 盐酸 、 sodium tetrahydroborate 、 氢溴酸 、 sodium 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 99.0h， 生成 N-[2-(4-chlorophenyl)sulfanylethyl]-2-(1H-imidazol-5-yl)ethanamine
  参考文献：
  名称：

  Acylated and alkylated histamine derivatives as new histamine H3-receptor antagonists

  摘要：

  New histamine H-3-receptor antagonists were prepared and investigated for their ability to increase synthesis and release of histamine mediated by inhibition of presynaptically located H-3-receptors. Acyl derivatives of histamine methylated at different positions show poor activity at H-3-receptors, whereas N-alpha-alkyl and particularly N-alpha-acyl derivatives of histamine possess moderate to good H-3-receptor antagonist activity. A not-too-bulky and lipophilic residue in an optimal distance of 3-4 methylene groups from the amide function leads to potent and selective H-3-receptor antagonists. N-alpha-Histamine-gamma-phenylbutyramide 11 and N-alpha-histamine-gamma-cyclohexylbutyramide 13 are H-3-receptor antagonists with -log K-i of 7.1 and 7.3, respectively. Structure-activity relationships of different substitution patterns are discussed.

  DOI：

  10.1016/0223-5234(94)90031-0
• 作为产物：
  描述：

  组胺 、 苯氧乙酸 在 N,N'-羰基二咪唑 作用下， 生成 N-[2-(1H-Imidazol-4-yl)-ethyl]-2-phenoxy-acetamide
  参考文献：
  名称：

  Acylated and alkylated histamine derivatives as new histamine H3-receptor antagonists

  摘要：

  New histamine H-3-receptor antagonists were prepared and investigated for their ability to increase synthesis and release of histamine mediated by inhibition of presynaptically located H-3-receptors. Acyl derivatives of histamine methylated at different positions show poor activity at H-3-receptors, whereas N-alpha-alkyl and particularly N-alpha-acyl derivatives of histamine possess moderate to good H-3-receptor antagonist activity. A not-too-bulky and lipophilic residue in an optimal distance of 3-4 methylene groups from the amide function leads to potent and selective H-3-receptor antagonists. N-alpha-Histamine-gamma-phenylbutyramide 11 and N-alpha-histamine-gamma-cyclohexylbutyramide 13 are H-3-receptor antagonists with -log K-i of 7.1 and 7.3, respectively. Structure-activity relationships of different substitution patterns are discussed.

  DOI：

  10.1016/0223-5234(94)90031-0