7-(4-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-piperidin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one | 1314032-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-(4-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-piperidin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 7-[4-[4-(2-oxo-3H-benzimidazol-1-yl)piperidin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one
• CAS: 1314032-12-6
• 化学式: C₂₅H₃₀N₄O₃
• 分子量: 434.538
• InChiKey: LETHKPPNRMMQLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  73.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(4-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-piperidin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one 、 草酸 以 乙醇 为溶剂， 生成 7-(4-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-piperidin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate
  参考文献：
  名称：

  Synthesis and characterization of selective dopamine D2 receptor ligands using aripiprazole as the lead compound

  摘要：

  A series of compounds structurally related to aripiprazole (1), an atypical antipsychotic and antidepressant used clinically for the treatment of schizophrenia, bipolar disorder, and depression, have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds also share structural elements with the classical D2-like dopamine receptor antagonists, haloperidol, N-methylspiperone, domperidone and benperidol. Two new compounds, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (6) and 7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl) butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (7) were found to (a) bind to the D-2 receptor subtype with high affinity (K-i values <0.3 nM), (b) exhibit >50-fold D-2 versus D-3 receptor binding selectivity and (c) be partial agonists at both the D-2 and D-3 receptor subtype. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.021
• 作为产物：
  描述：

  4-（2-酮酸-1-苯并咪唑）哌啶 、 7-(4-溴丁氧基)-3,4-二氢-2(1H)-喹啉酮 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 以67%的产率得到7-(4-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-piperidin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and characterization of selective dopamine D2 receptor ligands using aripiprazole as the lead compound

  摘要：

  A series of compounds structurally related to aripiprazole (1), an atypical antipsychotic and antidepressant used clinically for the treatment of schizophrenia, bipolar disorder, and depression, have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds also share structural elements with the classical D2-like dopamine receptor antagonists, haloperidol, N-methylspiperone, domperidone and benperidol. Two new compounds, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (6) and 7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl) butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (7) were found to (a) bind to the D-2 receptor subtype with high affinity (K-i values <0.3 nM), (b) exhibit >50-fold D-2 versus D-3 receptor binding selectivity and (c) be partial agonists at both the D-2 and D-3 receptor subtype. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.021

文献信息

• Synthesis and characterization of selective dopamine D2 receptor ligands using aripiprazole as the lead compound
  作者：Suwanna Vangveravong、Zhanbin Zhang、Michelle Taylor、Melissa Bearden、Jinbin Xu、Jinquan Cui、Wei Wang、Robert R. Luedtke、Robert H. Mach

  DOI：10.1016/j.bmc.2011.04.021

  日期：2011.6

  A series of compounds structurally related to aripiprazole (1), an atypical antipsychotic and antidepressant used clinically for the treatment of schizophrenia, bipolar disorder, and depression, have been prepared and evaluated for affinity at D2-like dopamine receptors. These compounds also share structural elements with the classical D2-like dopamine receptor antagonists, haloperidol, N-methylspiperone, domperidone and benperidol. Two new compounds, 7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (6) and 7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-1-yl) butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate (7) were found to (a) bind to the D-2 receptor subtype with high affinity (K-i values <0.3 nM), (b) exhibit >50-fold D-2 versus D-3 receptor binding selectivity and (c) be partial agonists at both the D-2 and D-3 receptor subtype. (C) 2011 Elsevier Ltd. All rights reserved.