4-Hydroxy-4-(1-trityl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid ethyl ester | 873215-54-4

• 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: 4-Hydroxy-4-(1-trityl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid ethyl ester
• CAS: 873215-54-4
• 化学式: C₃₀H₃₁N₃O₃
• 分子量: 481.594
• InChiKey: VVVJFJQIHVOSMS-UHFFFAOYSA-N

物化性质

• 沸点：
  608.6±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  67.59
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-4-(1-trityl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid ethyl ester 在 三氯化铝 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 4-(1H-Imidazol-2-yl)-4-phenyl-piperidine
  参考文献：
  名称：

  4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives, a novel class of selective δ-opioid agonists

  摘要：

  A novel series of 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives has been prepared and their synthesis described herein. In vitro affinities for delta-, mu-, and kappa-opioid receptors, as well as the functional activity in the [S-35]GTP gamma S assay are reported. The most potent and selective delta-opioid agonist 18a exhibited a K-i of 18 nM, and was > 258-fold and 28-fold selective over mu- and kappa-receptors, respectively; the compound is a full agonist with an EC50 value of 14 nM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.025
• 作为产物：
  描述：

  N-三苯甲基咪唑 、 N-乙氧羰基-4-哌啶酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以48%的产率得到4-Hydroxy-4-(1-trityl-1H-imidazol-2-yl)-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives, a novel class of selective δ-opioid agonists

  摘要：

  A novel series of 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives has been prepared and their synthesis described herein. In vitro affinities for delta-, mu-, and kappa-opioid receptors, as well as the functional activity in the [S-35]GTP gamma S assay are reported. The most potent and selective delta-opioid agonist 18a exhibited a K-i of 18 nM, and was > 258-fold and 28-fold selective over mu- and kappa-receptors, respectively; the compound is a full agonist with an EC50 value of 14 nM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.025

文献信息

• 4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives as non-peptidic selective δ-opioid agonists with potential anxiolytic/antidepressant properties. Part 2
  作者：Andrés A. Trabanco、Nancy Aerts、Rosa M. Alvarez、José I. Andrés、Inge Boeckx、Javier Fernández、Antonio Gómez、Frans E. Janssens、Joseph E. Leenaerts、Ana I. De Lucas、Encarna Matesanz、Thomas Steckler、Shirley Pullan

  DOI：10.1016/j.bmcl.2007.05.012

  日期：2007.7

  Novel 4-phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives have been prepared and their synthesis described herein. In vitro affinities for delta-, mu-, and kappa-opioid receptors are reported. Evaluation of some representative compounds from this series in the mouse neonatal ultrasonic vocalization test and the mouse tail suspension test revealed anxiolytic- and antidepressant-like effects, respectively, upon subcutaneous administration. (C) 2007 Elsevier Ltd. All rights reserved.