4-(2,3-dichlorophenyl)-1-piperazineethaneamine | 163620-93-7

• 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: 4-(2,3-dichlorophenyl)-1-piperazineethaneamine
• 英文别名: 2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethanamine；2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethanamine
• CAS: 163620-93-7
• 化学式: C₁₂H₁₇Cl₂N₃
• 分子量: 274.193
• InChiKey: IVOGRWCTFYUYEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-dichlorophenyl)-1-piperazineethaneamine 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成
  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：

  1-(2,3-二氯苯基)哌嗪 在 potassium carbonate 、 三乙胺 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4-(2,3-dichlorophenyl)-1-piperazineethaneamine
  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。
• <i>N</i>-(4-Arylpiperazinoalkyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1<i>H</i>-purine-2,6(3<i>H</i>,7<i>H</i>)-diones and their 5-HT₆, 5-HT₇, and D₂ receptors affinity
  作者：Paweł Żmudzki、Grzegorz Satała、Grażyna Chłoń-Rzepa、Andrzej J. Bojarski、Piotr Popik、Paweł Zajdel

  DOI：10.1515/hc-2014-0200

  日期：2015.2.1

  A series of N-(arylpiperazinyl)acetamide derivatives of 1,3- and 3,7-dimethyl-1H-purine-2,6(3H,7H)-dione was synthesized and biologically evaluated in in vitro competition binding experiments for serotonin 5-HT₆, 5-HT₇, and dopamine D₂ receptors. The structure-affinity relationships for this group of compounds allowed for determination of structural features responsible for receptor affinity. Among the investigated derivatives, compounds 5 and 12 with (2,3-dichlorophenyl)piperazine moiety were classified as potent dual 5-HT₆/D₂ receptors ligands, whereas compound 4, with 4-(benzo[d]isothiazol-3-yl)piperazine moiety, and compounds 8 and 15, with (2,3-dichlorophenyl)piperazine moiety, were classified as potent D₂ receptor ligands.

  合成了一系列N-(芳基哌嗪基)乙酰胺衍生物，包括1,3-二甲基-1H-嘌呤-2,6(3H,7H)-二酮和3,7-二甲基-1H-嘌呤-2,6(3H,7H)-二酮，并在体外竞争结合实验中对其进行了生物学评价，涉及5-羟色胺5-HT₆、5-HT₇和多巴胺D₂受体。这组化合物的结构-亲和力关系使得能够确定负责受体亲和力的结构特征。在研究的衍生物中，含有(2,3-二氯苯基)哌嗪基团的化合物5和12被归类为强效的双重5-HT₆/D₂受体配体，而含有4-(苯并[d]异噻唑-3-基)哌嗪基团的化合物4，以及含有(2,3-二氯苯基)哌嗪基团的化合物8和15，被归类为强效的D₂受体配体。

• [DE] CARBOXAMIDE DES INDOLIZINS UND SEINER AZA- UND DIAZADERIVATE<br/>[EN] INDOLIZINE CARBOXAMIDES AND THE AZA AND DIAZA DERIVATIVES THEREOF<br/>[FR] CARBOXAMIDES D'INDOLIZINE ET LEURS AZA- ET DIAZA-DERIVES
  申请人：SANOL ARZNEI SCHWARZ GMBH

  公开号：WO2006015737A1

  公开（公告）日：2006-02-16

  Die vorliegende Erfindung betrifft neurorezeptoraktive Carboxamid-substituierte Indolizin­-Derivate der allgemeinen Formel (I) wobei X eine Gruppe mit der allgemeinen Formel (X1) repräsentiert.

  本发明涉及具有神经受体活性的羧酰胺取代的吲哩啉衍生物，其一般式为（I），其中X代表一种具有一般式（X1）的基团。
• Click chemistry based solid phase supported synthesis of dopaminergic phenylacetylenes
  作者：Pilar Rodriguez Loaiza、Stefan Löber、Harald Hübner、Peter Gmeiner

  DOI：10.1016/j.bmc.2007.08.038

  日期：2007.12

  'Click resins' enable solid phase supported reactions to work under nearly perfect conditions fulfilling the requirements of click chemistry. Utilizing the formylpyrrolylmethyltriazole (FPMT) linker 6, which is readily available via copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), a BAL strategy could be successfully applied for a parallel synthesis of dopaminergic phenylacetylens. A focused

  “点击树脂”使固相支持的反应能够在满足点击化学要求的近乎完美的条件下进行。利用可通过铜（I）催化的叠氮化物-炔烃环加成（CuAAC）容易获得的甲酰基吡咯基甲基三唑（FPMT）接头6，BAL策略可以成功地应用于多巴胺能苯乙炔的平行合成。通过四步SPOS方法（包括微波辅助的Sonogashira偶联）生成了一个包含20种受试化合物的库，揭示了三点差异。GPCR-配体结合测定表明出色的多巴胺D3和D4受体结合亲和力，这些亲和力被确定对最有效的测试化合物2c，e，i，k引起部分激动剂活性。
• Naphthalamides as central nervous system agents
  申请人：Warner-Lambert Company

  公开号：US05395835A1

  公开（公告）日：1995-03-07

  Naphthalamides are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as antipsychotic agents and as agents for the treatment of disorders which respond to dopaminergic blockade including psychotic depression, substance abuse, and compulsive disorders.

  本发明涉及萘酰胺类化合物，以及制备该化合物的方法和制备药物组合物的方法，该药物组合物可用作中枢神经系统药物，特别是用作抗精神病药物以及用于治疗对多巴胺阻断有反应的疾病，包括精神抑郁症、物质滥用和强迫性障碍。