4-Pyrrolidin-3-ylmethyl-1H-imidazole | 151094-62-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Pyrrolidin-3-ylmethyl-1H-imidazole
• 英文别名: 5-[(pyrrolidin-3-yl)methyl]-1H-imidazole；5-(pyrrolidin-3-ylmethyl)-1H-imidazole
• CAS: 151094-62-1
• 化学式: C₈H₁₃N₃
• 分子量: 151.211
• InChiKey: YGGBVTGACIFVRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Pyrrolidin-3-ylmethyl-1H-imidazole 在 氢溴酸 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 VUF 4848
  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：

  N-benzyl-3-[hydroxy(triphenylmethylimidazol-4-yl)methyl]pyrrolidin-2-one 在 palladium dihydroxide 吡啶 、 lithium aluminium tetrahydride 、 硫酸 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、5.07 MPa 条件下， 反应 77.0h， 生成 4-Pyrrolidin-3-ylmethyl-1H-imidazole
  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

• [EN] 1-(1H-IMIDAZOL-2-YL)PYRROLIDINE AND 1-(1H-IMIDAZOL-2-YLPIPERIDINE) DERIVATIVES, PREPARATION AND THERAPEUTIC APPLICATION<br/>[FR] DERIVES DE 1-(1H-IMIDAZOL-2-YL)PYRROLIDINES ET 1-(1H-IMIDAZOL-2-YLPIPERIDINES), LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
  申请人：SANOFI-SYNTHELABO

  公开号：WO1999031089A1

  公开（公告）日：1999-06-24

  (EN) The invention concerns a compound of general formula (I) in which: R represents a hydrogen atom or a phenyl group optionally substituted by a halogen atom or a methyl, methoxy, trifluoromethyl or nitro group; X represents a hydrogen or halogen atom or a methyl, methoxy, trifluoromethyl or nitro group; n is equal to 1 or 2, and m is equal to 0 or 1. Said compound is applicable in therapeutics.(FR) Composé de formule générale (I) dans laquelle R représente un atome d'hydrogène ou un groupe phényle éventuellement substitué par un atome d'halogène ou un groupe méthyle, méthoxy, trifluorométhyle ou nitro, X représente un atome d'hydrogène ou d'halogène ou un groupe méthyle, méthoxy, trifluorométhyle ou nitro, n est égal à 1 ou à 2, et m est égal à 0 ou à 1. Application en thérapeutique.
• 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.