4(5)-(4-cyanobutyl)imidazole | 56866-60-5

• 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(5)-(4-cyanobutyl)imidazole
• 英文别名: 5-(1H-imidazol-5-yl)pentanenitrile
• CAS: 56866-60-5
• 化学式: C₈H₁₁N₃
• mdl: MFCD08668426
• 分子量: 149.195
• InChiKey: CBPXDNFRFIBHQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4(5)-(4-cyanobutyl)imidazole 在 盐酸 、 氨 作用下， 以 乙二醇 为溶剂， 反应 150.0h， 生成 2-[4-(3H-Imidazol-4-yl)-butyl]-5-phenyl-1H-imidazole
  参考文献：
  名称：

  Synthesis and biological assays of new H3-antagonists with imidazole and imidazoline polar groups

  摘要：

  New histamine H-3-receptor antagonists were synthesised and tested on rat brain membranes and on electrically stimulated guinea-pig ileum. The new compounds have a central polar group represented by a 2-alkylimidazole or a 2-thioimidazoline nucleus. The effect of the polar group basicity on the optimal length of the alkyl chain, connecting this group to a 4(5)-imidazolyl ring, was investigated. The best affinity values, obtained by displacement of [H-3]-RAMHA from rat brain, were obtained for the 2-alkylimidazole derivatives (2a-f) with tetramethylene chain (pK(i) 8.03-8.97), having an intermediate basicity between that of the previously reported 2-thioimidazoles (1a-i) and that of 2-alkylthioimidazolines (3a-h). In contrast, a general lowering of affinity (pK(i) 5.90-7.63) was observed for compounds of the last series (3a-h), with a complex dependence on the terminal lipophilic group and chain length. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00115-9
• 作为产物：
  描述：

  1-(Dimethylsulfamoyl)-5-(4-cyanobutyl)imidazole 在 盐酸 作用下， 以0.49 g的产率得到4(5)-(4-cyanobutyl)imidazole
  参考文献：
  名称：

  Synthesis and biological assays of new H3-antagonists with imidazole and imidazoline polar groups

  摘要：

  New histamine H-3-receptor antagonists were synthesised and tested on rat brain membranes and on electrically stimulated guinea-pig ileum. The new compounds have a central polar group represented by a 2-alkylimidazole or a 2-thioimidazoline nucleus. The effect of the polar group basicity on the optimal length of the alkyl chain, connecting this group to a 4(5)-imidazolyl ring, was investigated. The best affinity values, obtained by displacement of [H-3]-RAMHA from rat brain, were obtained for the 2-alkylimidazole derivatives (2a-f) with tetramethylene chain (pK(i) 8.03-8.97), having an intermediate basicity between that of the previously reported 2-thioimidazoles (1a-i) and that of 2-alkylthioimidazolines (3a-h). In contrast, a general lowering of affinity (pK(i) 5.90-7.63) was observed for compounds of the last series (3a-h), with a complex dependence on the terminal lipophilic group and chain length. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00115-9