(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-[4-(4-phenyl-piperazin-1-yl)-butyl]-propyl-amine | 477789-17-6

• 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-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-[4-(4-phenyl-piperazin-1-yl)-butyl]-propyl-amine
• 英文别名: 7-Methoxyl-2-[N-propyl-(N-(4-phenylpiperazin-1-yl)-butyl)amino]tetralin；7-methoxy-N-[4-(4-phenylpiperazin-1-yl)butyl]-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine
• CAS: 477789-17-6；1003565-77-2；1003565-78-3
• 化学式: C₂₈H₄₁N₃O
• 分子量: 435.653
• InChiKey: OYKARZYVMWEYDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  19
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-[4-(4-phenyl-piperazin-1-yl)-butyl]-propyl-amine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(+)-7-[(4-(4-Phenylpiperazin-1-yl)butyl)(propyl)amino]-5,6,7,8-tetrahydronaphthalen-2-ol
  参考文献：
  名称：

  杂化7-{[2-（4-苯基哌嗪-1-基）乙基]丙基氨基} -5,6,7,8-四氢萘-2-醇类似物的进一步构效关系研究：高亲和力D3的鉴定-具有强效体内活性且作用时间长的激动剂。

  摘要：

  本文介绍了一种针对多巴胺D2 / D3受体的氨基四氢萘-哌嗪类杂合分子的扩展结构-活性关系研究。已经开发出各种类似的作为位置异构体的类似物，其中酚羟基在芳族环上的位置已经改变。在两个邻苯二酚衍生物之间，具有两个亚甲基接头长度的化合物6e相对于具有四个亚甲基接头的化合物6f对D3的表现出更高的亲和力和对D3的选择性（6e和6f分别为D2 / D3 = 50.6 vs 7.51）。通常，（-）-异构体比（+）-异构体更有效。结合结果表明对化合物（-）-10中的D3受体具有最高选择性（K i = 0.35 nM； D2 / D3 = 71）。在5-羟基系列中，化合物（-）-25（K i = 0.）对D3受体的选择性最高。82 nM；D2 / D3 = 31.5）。大多数有效的化合物在亚纳摩尔水平上对D3受体表现出结合和功能亲和力。用tri化的烯酮作为放​​射性配体，用表达D2或D3受体的HEK-

  DOI：

  10.1021/jm070860r
• 作为产物：
  描述：

  4-(4-phenylpiperazin-1-yl)butan-1-amine 在 lithium aluminium tetrahydride 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成 (7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-[4-(4-phenyl-piperazin-1-yl)-butyl]-propyl-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

文献信息

• Hybrid 2-aminotetralin and aryl-substituted piperazine compounds and their use in altering cns activity
  申请人：——

  公开号：US20030195219A1

  公开（公告）日：2003-10-16

  Hybrid compounds containing in aminotetralin moiety or a heterocyclic and/or open chain analog thereof linked through an alkylene group to an aryl ring system-substituted piperidiene moiety exhibit high levels of CNS activity, in some cases exhibiting especially high relative binding efficiencies between D3 and D2 dopaminergic receptor subtypes.

  含有氨基四氢萘基团或其杂环和/或开链类似物的混合化合物，通过烷基基团连接到芳香环系统取代哌啶基团，表现出高水平的中枢神经系统活性，在某些情况下尤其表现出D3和D2多巴胺受体亚型之间的相对结合效率特别高。
• Hybrid 2-aminoterailin and aryl-substituted piperazine compounds and their use in altering CNS activity
  申请人：Dutta K. Aloke

  公开号：US20060020132A1

  公开（公告）日：2006-01-26

  Hybrid compounds containing an aminotetralin moiety or a heterocyclic and/or open chain analog thereof linked through an alkylene group to an aryl ring system-substituted piperidiene moiety exhibit high levels of CNS activity, in some cases exhibiting especially high relative binding efficiencies between D3 and D2 dopaminergic receptor subtypes.

  含有氨基四氢萘基团或杂环和/或开链类似物的混合化合物，通过烷基链连接到芳香环系统取代的哌啶基团，表现出高水平的中枢神经系统活性，在某些情况下表现出D3和D2多巴胺受体亚型之间特别高的相对结合效率。
• Hybrid 2-Aminotetralin and Aryl-Substituted Piperazine Compounds and their Use in Altering CNS Activity
  申请人：Dutta Aloke K.

  公开号：US20100210663A1

  公开（公告）日：2010-08-19

  Hybrid compounds containing an aminotetralin moiety or a heterocyclic and/or open chain analog thereof linked through an alkylene group to an aryl ring system-substituted piperidiene moiety exhibit high levels of CNS activity, in some cases exhibiting especially high relative binding efficiencies between D3 and D2 dopaminergic receptor subtypes.

  含有氨基四氢萘基团或其杂环和/或开链类似物的杂化化合物，通过烷基链连接到芳环系统取代的哌啶基团，表现出高水平的中枢神经系统活性，在某些情况下，表现出特别高的D3和D2多巴胺受体亚型之间相对结合效率。
• A novel series of hybrid compounds derived by combining 2-aminotetralin and piperazine fragments: binding activity at D2 and D3 receptors
  作者：Aloke K Dutta、Xiang-Shu Fei、Maarten E.A Reith

  DOI：10.1016/s0960-894x(01)00820-4

  日期：2002.2

  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.
• US6982332B2
  申请人：——

  公开号：US6982332B2

  公开（公告）日：2006-01-03