2-(-1-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-3-yl)acetonitrile | 944054-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(-1-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-3-yl)acetonitrile
• 英文别名: 2-[4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl]acetonitrile
• CAS: 944054-51-7
• 化学式: C₁₈H₁₃Cl₂N
• 分子量: 314.214
• InChiKey: IQSIWRJLFWMEBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(-1-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-3-yl)acetonitrile 在 硼烷四氢呋喃络合物 、 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.75h， 生成 2-(4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethanamine
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors

  摘要：

  The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activity. The detailed synthesis and in vitro activity and ADME profile of compounds is described, which represent a previously undisclosed triple reuptake inhibitor chemotype. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.034
• 作为产物：
  描述：

  4-(3,4-二氯苯基)-1-四氢萘酮 在 sodium tetrahydroborate 、 sodium hydrogen sulfate 、 四氧化锇 、 水 、 sodium hydride 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 甲基叔丁基醚 、 丙酮 、 甲苯 、 mineral oil 为溶剂， 反应 9.17h， 生成 2-(-1-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-3-yl)acetonitrile
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors

  摘要：

  The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activity. The detailed synthesis and in vitro activity and ADME profile of compounds is described, which represent a previously undisclosed triple reuptake inhibitor chemotype. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.10.034

文献信息

• Tetralone-based monoamine reuptake inhibitors
  申请人：Shao Liming

  公开号：US20070197588A1

  公开（公告）日：2007-08-23

  The invention relates to novel tetralone based amines and their use in the treatment of central nervous system (CNS) disorders, such as depression, attention deficit hyperactivity disorder (ADHD) and Parkinson's disease. The invention further relates to pharmaceutical compositions containing the compounds and compositions of the invention as well as methods of inhibiting reuptake of one or more monoamine, such as such as dopamine and norepinephrine, from the synaptic cleft, and methods of modulating one or more monoamine transporter.

  本发明涉及新型四氢萘基胺及其在治疗中枢神经系统（CNS）疾病，如抑郁症、注意缺陷多动障碍（ADHD）和帕金森病中的应用。本发明还涉及含有该化合物和本发明的组合物的制药组合物，以及抑制一个或多个单胺的再摄取，如多巴胺和去甲肾上腺素，从突触裂隙中的方法和调节一个或多个单胺转运体的方法。
• EP1978961B1
  申请人：——

  公开号：EP1978961B1

  公开（公告）日：2016-03-16
• US8053603B2
  申请人：——

  公开号：US8053603B2

  公开（公告）日：2011-11-08
• [EN] TETRALONE-BASED MONOAMINE REUPTAKE INHIBITORS<br/>[FR] INHIBITEURS DE RECAPTAGE DE MONOAMINE A BASE DE TETRALONE
  申请人：SEPRACOR INC

  公开号：WO2007081542A2

  公开（公告）日：2007-07-19

  (EN) The invention relates to novel tetralone based amines and their use in the treatment of central nervous system (CNS) disorders, such as depression, attention deficit hyperactivity disorder (ADHD) and Parkinson's disease. The invention further relates to pharmaceutical compositions containing the compounds and compositions of the invention as well as methods of inhibiting reuptake of one or more monoamine, such as such as dopamine and norepinephrine, from the synaptic cleft, and methods of modulating one or more monoamine transporter.(FR) L'invention concerne de nouvelles amines à base de tétralone et leur utilisation dans le traitement des troubles du système nerveux central (SNC), tels que la dépression, l'hyperactivité avec déficit de l'attention (ADHD) et la maladie de Parkinson. L'invention concerne également des compositions pharmaceutiques contenant les composés et les compositions de l'invention, ainsi que des procédés d'inhibition du recaptage d'une ou de plusieurs monoamines, telles que la dopamine et la norépinéphrine, dans la fente synaptique, et des procédés de modulation d'un ou de plusieurs transporteurs de monoamine.
• Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors
  作者：Liming Shao、Fengjiang Wang、Scott C. Malcolm、Jianguo Ma、Michael C. Hewitt、Una C. Campbell、Larry R. Bush、Nancy A. Spicer、Sharon R. Engel、Lakshmi D. Saraswat、Larry W. Hardy、Patrick Koch、Rudy Schreiber、Kerry L. Spear、Mark A. Varney

  DOI：10.1016/j.bmc.2010.10.034

  日期：2011.1

  The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activity. The detailed synthesis and in vitro activity and ADME profile of compounds is described, which represent a previously undisclosed triple reuptake inhibitor chemotype. (C) 2010 Elsevier Ltd. All rights reserved.