2-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dione | 877145-02-3

• 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: 2-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dione
• 英文别名: 2-[2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl]isoindole-1,3-dione
• CAS: 877145-02-3
• 化学式: C₂₀H₁₉Cl₂N₃O₂
• 分子量: 404.296
• InChiKey: ZWZDVGGJZLKLTE-UHFFFAOYSA-N

物化性质

• 沸点：
  566.0±50.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dione 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 肼 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 {2-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-ethyl}-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine
  参考文献：
  名称：

  A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors

  摘要：

  A series of 7-hydroxy-2-[N-alkyl-(N-(4-pheny1piperazine)-alkyl)amino]tetralins was developed based on a novel hybrid approach that combined 2-aminotetralin and arylpiperazine pharmacophoric moieties. Our preliminary study revealed that a four-methylene butyl linker produced very potent compounds for both the D-2 and D-3 receptors. Further structure-activity studies led to a novel template showing 50- to 100-fold selectivity for the D-3 receptor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00820-4
• 作为产物：
  描述：

  N-(2-溴乙基)邻苯二甲酰亚胺 、 1-(2,3-二氯苯基)哌嗪 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological characterization of novel hybrid 7-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-propyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol and their heterocyclic bioisosteric analogues for dopamine D2 and D3 receptors

  摘要：

  In a recent preliminary communication we described the development of a series of hybrid molecules for the dopamine D2 and D3 receptor subtypes. The design of these compounds was based on combining pharmacophoric elements of aminotetralin and piperazine molecular fragments derived from known dopamine receptor agonist and antagonist molecules. Molecules developed from this approach exhibited high affinity and selectivity for the D3 receptor as judged from preliminary [H-3]spiperone binding data. In this report, we have expanded our previous finding by developing additional novel molecules and additionally evaluated functional activities of these novel molecules in the [H-3]thymidine incorporation mitogenesis assay. The binding results indicated highest selectivity in the bioisosteric benzothiazole derivative N6-[2-(4-phenyl-piperazin-1-yl)-ethyl]-N6-propyl-4,5,6,7-tetrahydro-benzothiazole-2,6-diamine (14) for the D3 receptor whereas the racemic compound 7-({2-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-ethyl}-propyl-amino)-5,6,7,8-tetrahydro-naphthaten-2-ol (10c) showed the strongest potency. Mitogenesis studies to evaluate functional activity demonstrated potent agonist properties in these novel derivatives for both D2 and D3 receptors. In this regard, compound 7-{[4-(4-phenyl-piperazin-1-yl)-butyl]-prop-2-ynyl-amino}-5,6,7,8-tetrahydro-naphthalen-2-ol (7b) exhibited the most potent agonist activity at the D3 receptor, 10 times more potent than quinpirole and was also the most selective compound for the D3 receptor in this series. Racemic compound 10a was resolved; however, little separation of activity was found between the two enantiomers of 10a. The marginally more active enantiomer (-)-10a was examined in vivo using the 6-OH-DA induced unilaterally lesioned rat model to evaluate its activity in producing contralateral rotations. The results demonstrated that in comparison to the reference compound apomorphine, (-)-10a was quite potent in inducing contralateral rotations and exhibited longer duration of action. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.019

文献信息

• ARYLPIPERAZINE-CONTAINING PURINE DERIVATIVES AND USES THEREOF
  申请人：Lee Jinhwa

  公开号：US20120232090A1

  公开（公告）日：2012-09-13

  A novel arylpiperazine-containing purine derivatives and a pharmaceutical composition comprising the same as an active ingredient, which are useful for preventing or treating depressive disorders, are provided.

  一种含有芳基哌嗪的嘌呤衍生物以及包含其作为活性成分的药物组合物被提供，用于预防或治疗抑郁症。
• ARYLPIPERAZINE-CONTAINING PYRROLE 3-CARBOXAMIDE DERIVATIVES FOR TREATING DEPRESSIVE DISORDERS
  申请人：Lee Jinhwa

  公开号：US20110178091A1

  公开（公告）日：2011-07-21

  The present invention relates to novel arylpiperazine-containing pyrrole 3-carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof which is useful for preventing or treating depressive disorders. The present invention also provides a method for preparing the arylpiperazine-containing pyrrole 3-carboxamide derivatives or the pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating depressive disorders.

  本发明涉及一种新的芳基哌嗪含有吡咯3-羧酰胺衍生物的化合物（I），或其药学上可接受的盐，用于预防或治疗抑郁症。本发明还提供了制备芳基哌嗪含有吡咯3-羧酰胺衍生物或其药学上可接受的盐的方法，包括含有它们的药物组合物，以及预防或治疗抑郁症的方法。
• Arylpiperazine-containing purine derivatives and uses thereof
  申请人：Lee Jinhwa

  公开号：US08785453B2

  公开（公告）日：2014-07-22

  A novel arylpiperazine-containing purine derivatives and a pharmaceutical composition comprising the same as an active ingredient, which are useful for preventing or treating depressive disorders, are provided.

  本发明提供了一种新型芳基哌嗪含有嘌呤衍生物以及以其为活性成分的制药组合物，可用于预防或治疗抑郁症。
• Arylpiperazine-containing pyrrole 3-carboxamide derivatives for treating depressive disorders
  申请人：Lee Jinhwa

  公开号：US08895558B2

  公开（公告）日：2014-11-25

  The present invention relates to novel arylpiperazine-containing pyrrole 3-carboxamide derivatives of formula (I) or a pharmaceutically acceptable salt thereof which is useful for preventing or treating depressive disorders. The present invention also provides a method for preparing the arylpiperazine-containing pyrrole 3-carboxamide derivatives or the pharmaceutically acceptable salt thereof, a pharmaceutical composition containing same, and a method for preventing or treating depressive disorders.

  本发明涉及一种新的芳基哌嗪基吡咯-3-羧酰胺衍生物（I式）或其药学上可接受的盐，用于预防或治疗抑郁症。本发明还提供了一种制备芳基哌嗪基吡咯-3-羧酰胺衍生物或其药学上可接受的盐的方法，以及含有它的制药组合物和预防或治疗抑郁症的方法。
• [EN] ARYLPIPERAZINE-CONTAINING PYRROLE 3-CARBOXAMIDE DERIVATIVES FOR TREATING DEPRESSIVE DISORDERS<br/>[FR] DÉRIVÉS DE PYRROLE 3-CARBOXAMIDE CONTENANT DE L'ARYLPIPÉRAZINE POUR LE TRAITEMENT DE TROUBLES DÉPRESSIFS
  申请人：GREEN CROSS CORP

  公开号：WO2010038948A3

  公开（公告）日：2010-06-24