1-benzyl-4-[2-(1H-imidazol-5-yl)ethyl]piperidine | 639089-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-4-[2-(1H-imidazol-5-yl)ethyl]piperidine
• CAS: 639089-26-2
• 化学式: C₁₇H₂₃N₃
• 分子量: 269.39
• InChiKey: NKMDTVBCCZUNIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  31.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-[2-(1H-imidazol-5-yl)ethyl]piperidine 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 4-[2-(imidazol-4-yl)ethyl]piperidine
  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：

  3-(1-Benzyl-piperidin-4-yl)-propan-1-ol 在 草酰氯 、 氰化钠 、 氨 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.75h， 生成 1-benzyl-4-[2-(1H-imidazol-5-yl)ethyl]piperidine
  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

• <i>N</i>-Substituted Piperidinyl Alkyl Imidazoles:  Discovery of Methimepip as a Potent and Selective Histamine H₃ Receptor Agonist
  作者：Ruengwit Kitbunnadaj、Takeshi Hashimoto、Enzo Poli、Obbe P. Zuiderveld、Alessandro Menozzi、Ryoko Hidaka、Iwan J. P. de Esch、Remko A. Bakker、Wiro M. P. B. Menge、Atsushi Yamatodani、Gabriella Coruzzi、Henk Timmerman、Rob Leurs

  DOI：10.1021/jm049475h

  日期：2005.3.1

  efforts toward the development of potent and highly selective histamine H(3) receptor agonists. We introduced various alkyl or aryl alkyl groups on the piperidine nitrogen of the known H(3)/H(4) agonist immepip and its analogues (1-3a). We observed that N-methyl-substituted immepip (methimepip) exhibits high affinity and agonist activity at the human histamine H(3) receptor (pK(i) = 9.0 and pEC(50) = 9

  在这项研究中，我们继续努力发展有效和高度选择性的组胺H（3）受体激动剂。我们在已知的H（3）/ H（4）激动剂impipip及其类似物（1-3a）的哌啶氮上引入了各种烷基或芳基烷基。我们观察到N-甲基取代的immepip（methimepip）对人类组胺H（3）受体（pK（i）= 9.0和pEC（50）= 9.5）表现出高亲和力和激动剂活性，在该处的选择性是2000倍。人类H（3）受体超过人类H（4）受体，选择性超过人类H组胺H（1）和H（2）受体的10000倍以上。Methimepip在豚鼠回肠中作为H（3）受体激动剂也非常有效（pD（2）= 8.26）。而且，
• Synthesis and Structure−Activity Relationships of Conformationally Constrained Histamine H₃ Receptor Agonists
  作者：Ruengwit Kitbunnadaj、Obbe P. Zuiderveld、Iwan J. P. De Esch、Roeland C. Vollinga、Remko Bakker、Martin Lutz、Anthony L. Spek、Emile Cavoy、Marie-France Deltent、Wiro M. P. B. Menge、Henk Timmerman、Rob Leurs

  DOI：10.1021/jm030905y

  日期：2003.12.1

  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.