7-(4-(4-(2-methoxy-4-methylphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 7-(4-(4-(2-methoxy-4-methylphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one oxalate
• 英文别名: 7-[4-[4-(2-methoxy-4-methylphenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one;oxalic acid
• 化学式: C₂H₂O₄*C₂₅H₃₃N₃O₃
• 分子量: 513.591
• InChiKey: KQNQOTGDSHLFFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-甲氧基-4-甲基苯胺 在 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 、 乙腈 、 正丁醇 为溶剂， 生成 7-(4-(4-(2-methoxy-4-methylphenyl)piperazin-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

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.