2-(triphenylmethylimidazol-4-yl)-cyclopropylmethanol | 223419-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(triphenylmethylimidazol-4-yl)-cyclopropylmethanol
• 英文别名: [2-(1-Tritylimidazol-4-yl)cyclopropyl]methanol
• CAS: 223419-80-5
• 化学式: C₂₆H₂₄N₂O
• 分子量: 380.489
• InChiKey: XATLMDAZPXRBBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(triphenylmethylimidazol-4-yl)-cyclopropylmethanol 在 盐酸 、 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 11.5h， 生成 2-(1H-imidazol-5-yl)cyclopropylmethylamine dihydrochloride
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y
• 作为产物：
  描述：

  (+/-)-trans-ethyl 2-(1-triphenylmethylimidazol-4-yl)cyclopropanecarboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-(triphenylmethylimidazol-4-yl)-cyclopropylmethanol
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists

  摘要：

  Immepip, a conformationally constrained analogue of the histamine congener imbutamine, shows high affinity and functional activity on the human H-3 receptor. Using histamine and its homologues as prototypes, other rigid analogues containing either a piperidine or pyrrolidine ring in the side chain were synthesized and tested for their activities at the human H-3 receptor and the closely related H-4 receptor. In the series of piperidine containing analogues, immepip was found to be the most potent H-3 receptor agonist, whereas its propylene analogue 13a was identified as a high-affinity neutral antagonist for the human H-3 receptor. Moreover, replacement of the piperidine ring of immepip by a pyrrolidine ring led to a pair of enantiomers that show a distinct stereoselectivity at the human H-3 and H-4 receptor.

  DOI：

  10.1021/jm030905y

文献信息

• Novel alicyclic imidazoles as H3 agents
  申请人：——

  公开号：US20020042400A1

  公开（公告）日：2002-04-11

  Alicyclic imidazole compounds; pharmaceutically active compositions containing such compounds; and the use of such compounds in formulations for the control or prevention of disease states in which histamine H 3 receptors are involved, such as allergy, inflammation, hypotension, glaucoma, sleeping disorders, states of hyper- and hypo-motility of the gastro-intestinal tract, cardiovascular disease, hypo- and hyper-activity of the central nervous system, Alzheimer's, schizophrenia, obesity and migraines are disclosed.

  本文介绍了脂环咪唑化合物、含有这些化合物的药用组合物以及在控制或预防涉及组胺H3受体的疾病状态（如过敏、炎症、低血压、青光眼、睡眠障碍、胃肠道高低动力状态、心血管疾病、中枢神经系统低高活性、阿尔茨海默病、精神分裂症、肥胖症和偏头痛等）的制剂中使用此类化合物的方法。
• Novel alicylic imidazoles as H3 agents
  申请人：——

  公开号：US20040029943A1

  公开（公告）日：2004-02-12

  Alicyclic imidazole compounds; pharmaceutically active compositions containing such compounds; and the use of such compounds in formulations for the control or prevention of disease states in which histamine H 3 receptors are involved, such as allergy, inflammation, hypotension, glaucoma, sleeping disorders, states of hyper- and hypo-motility of the gastro-intestinal tract, cardiovascular disease, hypo- and hyper-activity of the central nervous system, Alzheimer's, schizophrenia, obesity and migraines are disclosed.

  本发明涉及脂环型咪唑化合物；含有这种化合物的药物活性组合物；以及在制剂中使用这种化合物来控制或预防组织胺H3受体参与的疾病状态，例如过敏、炎症、低血压、青光眼、睡眠障碍、胃肠道过度和过度活动状态、心血管疾病、中枢神经系统的低活性和高活性、阿尔茨海默病、精神分裂症、肥胖症和偏头痛。
• NOVEL ALICYCLIC IMIDAZOLES AS H 3 AGENTS
  申请人：GLIATECH, INC.

  公开号：EP1313470A1

  公开（公告）日：2003-05-28
• EP1313470A4
  申请人：——

  公开号：EP1313470A4

  公开（公告）日：2005-02-16
• US6794405B2
  申请人：——

  公开号：US6794405B2

  公开（公告）日：2004-09-21