7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one | 1085927-91-8

• 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-hydroxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 7-[4-[4-(2-hydroxyphenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one
• CAS: 1085927-91-8
• 化学式: C₂₃H₂₉N₃O₃
• 分子量: 395.502
• InChiKey: ALIQPUXDZCQATH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-溴-2-氟乙烷 、 7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以59%的产率得到7-(4-(4-(2-(2-fluoroethoxy)phenyl)piperazin-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
• 作为产物：
  描述：

  7-(4-(4-(2-methoxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one 在 aluminum (III) chloride 、 乙硫醇 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以20%的产率得到7-(4-(4-(2-hydroxyphenyl)piperazin-1-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Compositions, Synthesis, and Methods of Using Quinolinone Based Atypical Antipsychotic Agents

  摘要：

  本发明提供了新型喹诺酮衍生物，可以有效用于治疗精神分裂症及相关精神病，如急性躁狂症、双相情感障碍、自闭症和抑郁症。

  公开号：

  US20080293736A1

文献信息

• COMPOSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINONE BASED ATYPICAL ANTIPSYCHOTIC AGENTS
  申请人：Reviva Pharmaceuticals, Inc.

  公开号：EP2162135A1

  公开（公告）日：2010-03-17
• US8247420B2
  申请人：——

  公开号：US8247420B2

  公开（公告）日：2012-08-21
• [EN] COMPOSITIONS, SYNTHESIS, AND METHODS OF USING QUINOLINONE BASED ATYPICAL ANTIPSYCHOTIC AGENTS<br/>[FR] COMPOSITIONS, SYNTHÈSES ET PROCÉDÉS D'UTILISATION D'AGENTS ANTIPSYCHOTIQUES ATYPIQUES À BASE DE QUINOLINONE
  申请人：REVIVA PHARMACEUTICALS INC

  公开号：WO2008144764A1

  公开（公告）日：2008-11-27

  [EN] The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.
  [FR] La présente invention concerne de nouveaux dérivés de quinolinone qui peuvent être avantageusement utilisés pour traiter la schizophrénie et des psychoses apparentées telles que la manie aiguë, le trouble bipolaire, le trouble autistique et la dépression.
• 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.
• Compositions, Synthesis, and Methods of Using Quinolinone Based Atypical Antipsychotic Agents
  申请人：Bhat Laxminarayan

  公开号：US20080293736A1

  公开（公告）日：2008-11-27

  The present invention provides novel quinolinone derivatives which can be advantageously used for treating schizophrenia and related psychoses such as acute manic, bipolar disorder, autistic disorder, and depression.

  本发明提供了新型喹诺酮衍生物，可以有效用于治疗精神分裂症及相关精神病，如急性躁狂症、双相情感障碍、自闭症和抑郁症。