1-[3-[2-[4-(2-甲基-5-喹啉基)-1-哌嗪基]乙基]苯基]-2-咪唑烷酮 | 844903-58-8

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-[3-[2-[4-(2-甲基-5-喹啉基)-1-哌嗪基]乙基]苯基]-2-咪唑烷酮
• 英文名称: 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone
• 英文别名: 1-(3-(2-(4-(2-Methyl-5-quinolinyl)-1-piperazinyl)ethyl)phenyl)-2-imidazolidinone；1-[3-[2-[4-(2-methylquinolin-5-yl)piperazin-1-yl]ethyl]phenyl]imidazolidin-2-one
• CAS: 844903-58-8
• 化学式: C₂₅H₂₉N₅O
• 分子量: 415.538
• InChiKey: ANGUXJDGJCHGOG-UHFFFAOYSA-N

物化性质

• 密度：
  1.216±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：16.5 mg/ml（39.71 mM）

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[3-[2-[4-(2-甲基-5-喹啉基)-1-哌嗪基]乙基]苯基]-2-咪唑烷酮 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 生成 1-(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone dihydrochloride
  参考文献：
  名称：

  发现1-（3- {2- [4-（2-甲基-5-喹啉基）-1-哌嗪基]乙基}苯基）-2-咪唑啉酮（GSK163090），这是一种有效的，选择性的和口服活性的5-HT 1A / B / D受体拮抗剂

  摘要：

  为了鉴定5-HT 1自身受体的选择性药物如泛拮抗剂，进行了研究以阐明先前报道的双重作用的5-HT 1拮抗剂/ SSRI结构。鉴定出一系列新颖的化合物，它们显示出较低的内在活性和对5-HT 1A，5-HT 1B和5-HT 1D受体的有效亲和力以及对5-羟色胺转运蛋白的高选择性。在这些化合物中，1-（3- {2- [4-（2-甲基-5-喹啉基）-1-哌嗪基]乙基}苯基）-2-咪唑啉酮（36）被发现具有强大的体内活性和强大的临床前可开发性，并且在此基础上将其选择为候选药物，目的是评估其作为快速发作的抗抑郁药/抗焦虑药的潜力。

  DOI：

  10.1021/jm100714c
• 作为产物：
  描述：

  1-[3-(2-hydroxyethyl)phenyl]-2-imidazolidinone 在 碳酸甲丙酯 、 N,N-二异丙基乙胺 作用下， 以 丙腈 为溶剂， 反应 10.5h， 生成 1-[3-[2-[4-(2-甲基-5-喹啉基)-1-哌嗪基]乙基]苯基]-2-咪唑烷酮
  参考文献：
  名称：

  Route Selection and Process Development for a 5-Piperazinylquinaldine Derivative for the Treatment of Depression and Anxiety

  摘要：

  1-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)-2-imidazolidinone, 1, was identified as a potential drug for the treatment of depression and anxiety. Herein is described the work carried out to select the manufacturing route and the process research studies to optimize the key stages of route B. A particular focus is given to the genotoxic impurities, related to this route, as one of the intermediates of the manufacturing route was genotoxic and many genotoxic impurities can be formed in the process. Quality by Design principles were applied for the definition of the control strategy of these impurities.

  DOI：

  10.1021/op200140v

文献信息

• [EN] QUINOLINE AND QUINAZOLINE DERIVATIVES HAVING AFFINITY FOR 5HT1-TYPE RECEPTORS<br/>[FR] DERIVES DE QUINOLINE ET DE QUINAZOLINE PRESENTANT UNE AFFINITE VIS-A-VIS DES RECEPTEURS DU TYPE 5HT1
  申请人：GLAXO GROUP LTD

  公开号：WO2005014552A1

  公开（公告）日：2005-02-17

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R1, m, X, R2, n, W, p, Y, Z, R3, R4, R5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供了式(I)的化合物及其药用盐：其中R1、m、X、R2、n、W、p、Y、Z、R3、R4、R5和q的含义如描述中所定义。还公开了制备方法以及在治疗中的用途，特别是用于抑郁症或焦虑等中枢神经系统疾病。
• Quinoline and quinazoline derivatives having affinity for 5ht1-type receptors
  申请人：Bergauer Markus

  公开号：US20060229312A1

  公开（公告）日：2006-10-12

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R 1 , m, X, R 2 , n, W, p, Y, Z, R 3 , R 4 , R 5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供式(I)的化合物和药学上可接受的盐：其中R1，m，X，R2，n，W，p，Y，Z，R3，R4，R5和q的含义如描述中所定义。还公开了制备方法以及在治疗中的用途，特别是用于中枢神经系统疾病，如抑郁症或焦虑症。
• Quinoline and quinazoline derivatives having affinity for 5HT1-type receptors
  申请人：Glaxo Group Limited

  公开号：US07279481B2

  公开（公告）日：2007-10-09

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R1, m, X, R2, n, W, p, Y, Z, R3, R4, R5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供化学式（I）的化合物及其药学上可接受的盐： 其中R1，m，X，R2，n，W，p，Y，Z，R3，R4，R5和q的含义如描述中所定义。还公开了其制备方法和在治疗中的用途，特别是用于中枢神经系统疾病，如抑郁症或焦虑症。
• QUINOLINE AND QUINAZOLINE DERIVATIVES HAVING AFFINITY FOR 5HT1-TYPE RECEPTORS
  申请人：Bergauer Markus

  公开号：US20070167423A1

  公开（公告）日：2007-07-19

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are provided: wherein R 1 , m, X, R 2 , n, W, p, Y, Z, R 3 , R 4 , R 5 and q have the meanings as defined in the description. Methods of preparation and uses thereof in therapy, particularly for CNS disorders such as depression or anxiety, are also disclosed.

  提供了式(I)的化合物及其药学上可接受的盐： 其中，R1、m、X、R2、n、W、p、Y、Z、R3、R4、R5和q的含义如描述中定义的那样。还公开了其制备方法和在治疗中的用途，特别是用于中枢神经系统疾病如抑郁症或焦虑症。
• Quinoline and Quinazoline Derivatives Having Affinity for 5HT1-Type Receptors
  申请人：Bergauer Markus

  公开号：US20100204273A1

  公开（公告）日：2010-08-12

  Disclosed are methods for use of compounds of formula (I) in the treatment of CNS disorders such as dysthymia, schizophrenia, panic disorder, obsessive compulsive disorder, post-traumatic stress disorder, pain, and memory disorders: wherein R 1 , m, X, R 2 , n, W, p, Y, Z, R 3 , R 4 , R 5 and q have the meanings as defined in the description.

  本发明揭示了使用式（I）化合物治疗中枢神经系统疾病，如心境不良、精神分裂症、惊恐障碍、强迫症、创伤后应激障碍、疼痛和记忆障碍的方法：其中R1，m，X，R2，n，W，p，Y，Z，R3，R4，R5和q的含义如描述中定义的那样。