7-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one | 72566-41-7

• 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-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: SWR-1-8；7-{3-[4-(2-methoxy-phenyl)-piperazin-1-yl]-propoxy}-3,4-dihydro-1H-quinolin-2-one；7-{3-[4-(2-methoxyphenyl)piperazinyl]propoxy}-3,4-dihydrocarbostyril；7-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3,4-dihydro-1H-quinolin-2-one
• CAS: 72566-41-7
• 化学式: C₂₃H₂₉N₃O₃
• 分子量: 395.502
• InChiKey: XRXBZJLXUCSIKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.04
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3,4-二氢-7-羟基-2(1H)-喹啉酮 在 氢氧化钾 、 sodium iodide 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 18.0h， 生成 7-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propoxy)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.

  摘要：

  为了开发一种新型的神经安定药物，合成了一系列ω-(4-苯基-1-哌嗪基)-烷氧基-2(1H)-喹啉酮衍生物，并测试了它们的抗甲基苯丙胺和抗肾上腺素活性。大多数衍生物在3-(3, 4-二羟基苯基)-L-天冬氨酸（L-DOPA）和甲基苯丙胺处理的小鼠的跳跃行为测试中显示出强效的抗甲基苯丙胺活性，或者在甲基苯丙胺处理的小鼠的致死性测试中表现出显著效果。它们还表现出相对较高的抗肾上腺素效能，这取决于取代基在4-苯基-1-哌嗪基上的性质或数量；其中一些化合物在小鼠中仅引起轻微的强直症。在这些化合物中，7-{3-[4-(2, 3-二甲基苯基)-1-哌嗪基]丙氧基}-2(1H)-喹啉酮（OPC-4392），被认为是一种多巴胺自受体激动剂，已被选定用于进一步研究。同时，本文也讨论了结构-活性关系。

  DOI：

  10.1248/cpb.36.4377

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.
• BANNO, KAZUO;FUJIOKA, TAKAFUMI;KIKUCHI, TETSURO;OSHIRO, YASUO;HIYAMA, TAK+, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4377-4388
  作者：BANNO, KAZUO、FUJIOKA, TAKAFUMI、KIKUCHI, TETSURO、OSHIRO, YASUO、HIYAMA, TAK+

  DOI：——

  日期：——
• US4734416A
  申请人：——

  公开号：US4734416A

  公开（公告）日：1988-03-29
• US4824840A
  申请人：——

  公开号：US4824840A

  公开（公告）日：1989-04-25
• Studies on 2(1H)-quinolinone derivatives as neuroleptic agents. I. Synthesis and biological activities of (4-phenyl-1-piperazinyl)-propoxy-2(1H)-quinolinone derivatives.
  作者：KAZUO BANNO、TAKAFUMI FUJIOKA、TETSURO KIKUCHI、YASUO OSHIRO、TAKASHI HIYAMA、KAZUYUKI NAKAGAWA

  DOI：10.1248/cpb.36.4377

  日期：——

  With the aim of developing a novel neuroleptic drug, a series of ω-(4-phenyl-1-piperazinyl)-alkoxy-2 (1H)-quinolinone derivatives have been synthesized and tested for anti-methamphetamine and anti-epinephrine activities. Most of the derivatives were found to possess a potent antimethamphetamine activity in the jumping behavior test on mice treated with 3-(3, 4-dihydroxyphenyl)-L-alanine (L-DOPA) and methamphetamine, or in the lethality test with methamphetamine-treated mice. They also showed relatively high anti-epinephrine potency depending on the nature or number of substituents on the phenyl group in the 4-phenyl-1-piperazinyl moiety; some of these compounds induced only weak catalepsy in mice. Among them, 7-3-[4-(2, 3-dimethylphenyl)-1-piperazinyl]propoxy}-2 (1H)-quinolinone (OPC-4392), which was suggested to be a dopamine autoreceptor agonist, was selected for further investigations. The structure-activity relationships are also discussed.

  为了开发一种新型的神经安定药物，合成了一系列ω-(4-苯基-1-哌嗪基)-烷氧基-2(1H)-喹啉酮衍生物，并测试了它们的抗甲基苯丙胺和抗肾上腺素活性。大多数衍生物在3-(3, 4-二羟基苯基)-L-天冬氨酸（L-DOPA）和甲基苯丙胺处理的小鼠的跳跃行为测试中显示出强效的抗甲基苯丙胺活性，或者在甲基苯丙胺处理的小鼠的致死性测试中表现出显著效果。它们还表现出相对较高的抗肾上腺素效能，这取决于取代基在4-苯基-1-哌嗪基上的性质或数量；其中一些化合物在小鼠中仅引起轻微的强直症。在这些化合物中，7-3-[4-(2, 3-二甲基苯基)-1-哌嗪基]丙氧基}-2(1H)-喹啉酮（OPC-4392），被认为是一种多巴胺自受体激动剂，已被选定用于进一步研究。同时，本文也讨论了结构-活性关系。