4-(2,3-dichlorophenyl)piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(2,3-dichlorophenyl)piperidine
• 化学式: C₁₁H₁₃Cl₂N
• mdl: MFCD05189910
• 分子量: 230.137
• InChiKey: YODQESWJUQGRPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(4-bromobutoxy)-2-methylbenzo[d]thiazole 、 4-(2,3-dichlorophenyl)piperidine 在 sodium iodide 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.5h， 以61%的产率得到5-(4-(4-(2,3-dichlorophenyl)piperidin-1-yl)butoxy)-2-methylbenzo[d]thiazole
  参考文献：
  名称：

  Discovery of G Protein-Biased D2 Dopamine Receptor Partial Agonists

  摘要：

  Biased ligands (also known as functionally selective ligands) of G protein-coupled receptors are valuable tools for dissecting the roles of G protein-dependent and independent signaling pathways in health and disease. Biased ligands have also been increasingly pursued by the biomedical community as promising therapeutics with improved efficacy and reduced side effects compared with unbiased ligands. We previously discovered first-in-class,beta-arrestin-biased agonists of dopamine D2 receptor (D2R) by extensively exploring multiple regions of aripiprazole, a balanced D2R agonist. In our continuing efforts to identify biased agonists of D2R, we unexpectedly discovered a G protein-biased agonist of D2R, compound 1, which is the first G protein-biased D2R agonist from the aripiprazole scaffold. We designed and synthesized novel analogues to explore two regions of 1 and conducted structure functional selectivity relationship (SFSR) studies. Here we report the discovery of 1, findings from our SFSR studies, and characterization of novel G protein-biased D2R agonists.

  DOI：

  10.1021/acs.jmedchem.6b01208
• 作为产物：
  描述：

  4-(2,3-Dichlorophenyl)-1,2,3,6-tetrahydropyridine 、 盐酸 在 氧化铂 氢气 、 disodium;carbonate 、 乙酸乙酯 、 magnesium sulfate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-(2,3-dichlorophenyl)piperidine
  参考文献：
  名称：

  Disubstituted phenylpiperidines as modulators of dopamine and serotonin neurotransmission

  摘要：

  本发明涉及具有治疗中枢神经系统疾病的作用的化合物，特别是新的4-(邻、间二取代苯基)-1-烷基哌啶，其中R1、R2和R3如所定义。

  公开号：

  US07851629B2
• 作为试剂：
  描述：

  盐酸 、 benzyl 4-(2,3-dichlorophenyl)piperidine-1-carboxylate 在 乙醚 、 4-(2,3-dichlorophenyl)piperidine 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以to give 4-(2,3-dichlorophenyl)piperidine (intermediate 47) (3.5 g, 92%) as a white solid的产率得到4-(2,3-dichlorophenyl)piperidine
  参考文献：
  名称：

  Novel Functionally Selective Ligands of Dopamine D2 Receptors

  摘要：

  本发明涉及多巴胺D2受体的新型功能选择性配体，包括激动剂、拮抗剂和反向激动剂，其中图1为配体结构。本发明还涉及使用这些化合物治疗与D2受体相关的中枢神经系统疾病。

  公开号：

  US20130137679A1

文献信息

• Phenoxypropylamine compounds
  申请人：——

  公开号：US20020111358A1

  公开（公告）日：2002-08-15

  The present invention relates to a phenoxypropylamine compound of the formula (I) 1 wherein each symbol is as defined in the specification, an optically active compound thereof or a pharmaceutically acceptable salt thereof and hydrates thereof, which simultaneously show selective affinity for and antagonistic activity against 5-HT 1A receptor, as well as 5-HT reuptake inhibitory activity, and can be used as antidepressants quick in expressing an anti-depressive effect.

  本发明涉及一种公式（I）中的苯氧丙胺化合物： 1 其中每个符号如说明书中所定义，其光学活性化合物或其药物可接受的盐及水合物，同时显示出对5-HT 1A 受体的选择性亲和力和拮抗活性，以及5-HT再摄取抑制活性，并且可以用作快速表达抗抑郁效果的抗抑郁药。
• [EN] POSITIVE ALLOSTERIC MODULATORS OF MGLUR2<br/>[FR] MODULATEURS ALLOSTÉRIQUES POSITIFS DE MGLUR2
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2013192306A1

  公开（公告）日：2013-12-27

  The disclosure generally relates to compounds of formula I, including their salts, as well as compositions and methods of using the compounds. The compounds modulate the mGluR2 receptor and may be useful for the treatment of various disorders of the central nervous system. Formula (I):

  本公开通常涉及公式I的化合物，包括它们的盐，以及使用这些化合物的组合物和方法。这些化合物可以调节mGluR2受体，并且可能用于治疗中枢神经系统的各种疾病。公式（I）：
• [EN] NEW SUBSTITUTED PIPERIDINES AS MODULATORS OF DOPAMINE NEUROTRANSMISSION<br/>[FR] NOUVELLES PIPERIDINES SUBSTITUEES UTILISEES COMME MODULATEURS DE LA NEUROTRANSMISSION DE LA DOPAMINE
  申请人：CARLSSON A RESEARCH AB

  公开号：WO2005121092A1

  公开（公告）日：2005-12-22

  The present invention relates to compounds having therapeutic effects against disorders in the central nervous system, and in particular substituted hydroxypiperidines of the formula 1: wherein R1, R2, and R3 are as defined herein.

  本发明涉及具有治疗中枢神经系统疾病作用的化合物，特别是具有如下式1的取代羟基哌啶化合物：其中R1、R2和R3如本文所定义。
• SUBSTITUTED PIPERIDINES AS MODULATORS OF DOPAMINE NEUROTRANSMISSION
  申请人：Sonesson Clas

  公开号：US20070270467A1

  公开（公告）日：2007-11-22

  The present invention relates to compounds having therapeutic effects against disorders in the central nervous system, and in particular substituted hydroxypiperidines of the formula 1: wherein R1, R2, and R3 are as defined herein.

  本发明涉及具有对中枢神经系统疾病具有治疗作用的化合物，特别是公式1中的取代羟基哌啶：其中R1、R2和R3如本文所定义。
• NEW DISUBSTITUTED PHENYLPIPERIDINES AS MODULATORS OF DOPAMINE AND SEROTONIN NEUROTRANSMISSION
  申请人：Sonesson Clas

  公开号：US20070179185A1

  公开（公告）日：2007-08-02

  The present invention relates to compounds which have therapeutic effects against disorders in the central nervous system, and in particular new 4-(ortho,meta-disubstituted phenyl)-1-alkypiperidines. wherein R1, R2, and R3 are as defined.

  本发明涉及对中枢神经系统障碍具有治疗效果的化合物，特别是新的4-(邻,间二取代苯基)-1-烷基哌啶，其中R1，R2和R3如定义。