1-(naphthalen-1-yl)-3-(S)-methylpiperazine | 439081-70-6

• 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: 1-(naphthalen-1-yl)-3-(S)-methylpiperazine
• 英文别名: (S)-3-methyl-1-(naphth-1-yl)piperazine；(3S)-3-methyl-1-(1-naphthyl)piperazine；(3S)-3-methyl-1-naphthalen-1-ylpiperazine
• CAS: 439081-70-6
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: VNCLFUNSMLXUGW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(naphthalen-1-yl)-3-(S)-methylpiperazine 生成 1-{2-[(2S)-2-Methyl-4-(1-naphthyl)piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carboxamide
  参考文献：
  名称：

  Pharmaceutical compounds

  摘要：

  这项发明涉及到式(I)的化合物，其中R1至R12，—W—V—，—X—Y—，m和n的值如权利要求1中定义的，它们的制备和用作药物。

  公开号：

  US20040122001A1
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 生成 1-(naphthalen-1-yl)-3-(S)-methylpiperazine
  参考文献：
  名称：

  具有5-HT1D拮抗剂活性的新型选择性强效5-HT再摄取抑制剂：一系列噻吩并吡喃衍生物的化学和药理学评估。

  摘要：

  已经制备了一系列结合萘基哌嗪和噻吩并吡喃骨架的化合物，并评估了具有5-HT1D拮抗剂活性的5-HT再摄取抑制作用。这些化合物的设计基于“重叠类型”策略，其中两个药效团连接在一个分子中。所得的双重药理学特征具有提供更有效的抑郁症治疗的潜力。

  DOI：

  10.1016/j.bmc.2004.07.059

文献信息

• Arylpiperazine derivatives and use thereof as 5-HT1A receptor ligands
  申请人：Cepa Schwarz Pharma s.l.

  公开号：EP1674103A1

  公开（公告）日：2006-06-28

  Novel substituted arylpiperazine derivatives with activity as 5-hydroxytryptamine 1A (5-HT1A) receptor subtype ligands, to their stereochemical isomers, methods of their preparation, and to their use and to pharmaceutical compositions containing them for the treatment of Parkinson disease, cerebral damage by thromboembolic ictus, craneoencephalic traumatisms, depression, migraine, pain, psychosis, anxiety disorders, aggressive disorders or urinary tract disorders.

  这篇文章介绍了一种替代芳基哌嗪衍生物的小说，它具有作为5-羟色胺1A（5-HT1A）受体亚型配体的活性，以及它们的立体化异构体、制备方法、以及它们的用途和包含它们的制药组合物，用于治疗帕金森病、血栓栓塞性卒中引起的脑损伤、颅脑创伤、抑郁症、偏头痛、疼痛、精神病、焦虑症、攻击性疾病或泌尿道疾病。
• ARYLPIPERAZINE DERIVATIVE AND USE THEREOF AS 5-HT1A RECEPTOR LIGANDS
  申请人：Lopez-Rodriguez Maria Luz

  公开号：US20090036455A1

  公开（公告）日：2009-02-05

  Novel substituted arylpiperazine derivatives with activity as 5-hydroxytryptamine 1A (5-HT 1A ) receptor subtype ligands, to their stereochemical isomers, methods of their preparation, and to their use and to pharmaceutical compositions containing them for the treatment of Parkinson disease, cerebral damage by thromboembolic ictus, craneoencephalic traumatisms, depression, migraine, pain, psychosis, anxiety disorders, aggressive disorders or urinary tract disorders.

  小说替代了具有5-羟色胺1A（5-HT1A）受体亚型配体活性的芳基哌嗪衍生物，包括它们的立体化异构体、制备方法以及它们在治疗帕金森病、血栓栓塞性卒中引起的脑损伤、颅脑外伤、抑郁症、偏头痛、疼痛、精神病、焦虑症、攻击性障碍或泌尿道障碍的药物组成物中的使用。
• Synthesis and Structure−Activity Relationships of a New Model of Arylpiperazines. 8. Computational Simulation of Ligand−Receptor Interaction of 5-HT_1AR Agonists with Selectivity over α₁-Adrenoceptors
  作者：María L. López-Rodríguez、Maria José Morcillo、Esther Fernández、Bellinda Benhamú、Ignacio Tejada、David Ayala、Alma Viso、Mercedes Campillo、Leonardo Pardo、Mercedes Delgado、Jorge Manzanares、José A. Fuentes

  DOI：10.1021/jm048999e

  日期：2005.4.1

  We have designed and synthesized a new series of arylpiperazines V exhibiting high 5-HT1AR affinity and selectivity over alpha(1)-adrenoceptors. The new selective 5-HT1AR ligands contain a hydantoin (m = 0) or diketopiperazine (m = 1) moiety and an arylpiperazine moiety separated by one methylene unit (n = 1). The aryl substituent of the piperazine moiety (Ar) consists of different benzofused rings mimicking the favorable voluminous substituents at ortho and meta positions predicted by 3D-QSAR analysis in the previously reported series I. In particular, (S)-2-[[4-(naphth-1-yl)piperazin-1-yl]methyl]-1,4-dioxoperhydropyrrolo[1,2-a]pyrazine [(S)-9, CSP-2503] (5-HT1A, K-i = 4.1 nM; alpha(1), Ki > 1000 nM) has been pharmacologically characterized as a 5-HT1AR agonist at somatodendritic and postsynaptic sites, endowed with anxiolytic properties. Ligand (S)-9 is predicted, in computer simulations, to bind Asp(3.32) in TMH 3, Thr(5.39) and Ser(5.42) in TMH 5, and Trp(6.48) in TMH 6. We propose that agonists modify, by means of an explicit hydrogen bond, the conformation of Trp(6.48) from pointing toward TMH 7, in the inactive gauche+ conformation, to pointing toward the ligand binding site, in the active trans conformation.
• PHARMACEUTICAL COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1345930A2

  公开（公告）日：2003-09-24
• ARYLPIPERAZINE DERIVATIVES AND USE THEREOF AS 5-HT1A RECEPTOR LIGANDS
  申请人：Schwarz Pharma, S.L.

  公开号：EP1830854A1

  公开（公告）日：2007-09-12