1-((1H-indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol | 1240407-19-5

• 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-((1H-indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol
• 英文别名: 1-((1H-Indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol oxalate；1-(1H-indol-3-ylmethyl)-4-(4-iodophenyl)piperidin-4-ol
• CAS: 1240407-19-5
• 化学式: C₂₀H₂₁IN₂O
• 分子量: 432.304
• InChiKey: DKMWFGJOMJUBOA-UHFFFAOYSA-N

物化性质

• 沸点：
  574.2±50.0 °C(Predicted)
• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((1H-indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol 、 草酸 以 乙酸乙酯 为溶剂， 生成 1-((1H-indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol oxalate
  参考文献：
  名称：

  Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626

  摘要：

  A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (7), were found to have high affinity to and selectivity for D2 versus D3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D2 binding affinity and the D2 versus D3 selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.052
• 作为产物：
  描述：

  芦竹碱 、 4-(4-iodophenyl)-4-hydroxypiperidine 以 甲苯 为溶剂， 生成 1-((1H-indol-3-yl)methyl)-4-(4-iodophenyl)piperidin-4-ol
  参考文献：
  名称：

  Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626

  摘要：

  A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (7), were found to have high affinity to and selectivity for D2 versus D3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D2 binding affinity and the D2 versus D3 selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.052

文献信息

• Synthesis and characterization of selective dopamine D2 receptor antagonists. 2. Azaindole, benzofuran, and benzothiophene analogs of L-741,626
  作者：Suwanna Vangveravong、Michelle Taylor、Jinbin Xu、Jinquan Cui、Wesley Calvin、Sonja Babic、Robert R. Luedtke、Robert H. Mach

  DOI：10.1016/j.bmc.2010.05.052

  日期：2010.7

  A series of indole, 7-azaindole, benzofuran, and benzothiophene compounds have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds share structural elements with the classical D2-like dopamine receptor antagonists haloperidol, N-methylspiperone and benperidol. Two new compounds, 4-(4-iodophenyl)-1-((4-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (6) and 4-(4-iodophenyl)-1-((5-methoxy-1H-indol-3-yl) methyl) piperidin-4-ol (7), were found to have high affinity to and selectivity for D2 versus D3 receptors. Changing the aromatic ring system from an indole to other heteroaromatic ring systems reduced the D2 binding affinity and the D2 versus D3 selectivity. (C) 2010 Elsevier Ltd. All rights reserved.