4-allyl-1-(3-chlorophenyl)piperazine | 141511-00-4

• 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-allyl-1-(3-chlorophenyl)piperazine
• 英文别名: 1-Allyl-4-(3-chloro-phenyl)-piperazine；1-(3-chlorophenyl)-4-prop-2-enylpiperazine
• CAS: 141511-00-4
• 化学式: C₁₃H₁₇ClN₂
• 分子量: 236.744
• InChiKey: XEMWXLIWDOJAHL-UHFFFAOYSA-N

物化性质

• 沸点：
  342.7±42.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11H-dibenzo[b,e]azepine 5-oxide 、 4-allyl-1-(3-chlorophenyl)piperazine 以 甲苯 为溶剂， 反应 16.0h， 生成 4-[[4-(3-Chlorophenyl)piperazin-1-yl]methyl]-3-oxa-2-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7,9,11,14,16-hexaene
  参考文献：
  名称：

  Synthesis and structure–activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: a novel series of 5-HT2A/2C receptor antagonists. Part 1

  摘要：

  The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H-1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the svnthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A 2C c receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00721-1
• 作为产物：
  描述：

  3-溴丙烯 、 1-(3-氯苯基)哌嗪 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 4-allyl-1-(3-chlorophenyl)piperazine
  参考文献：
  名称：

  中枢神经系统制剂的结构活性关系研究。5.烃链对4-取代的1-（3-氯苯基）哌嗪对5-HT1A受体位点的亲和力的影响。

  摘要：

  研究了模型4-取代的1-（3-氯苯基）哌嗪12-31的烃链对其对5-HT1A受体位点的亲和力的影响。发现4-正烷基链的延长强烈增加了所研究化合物的5-HT1A亲和力。正己基衍生物20的亲和力达到最大值（Ki ＝ 2.67nM）。已表明1-芳基哌嗪的N-4取代基的疏水相互作用显着地促进了它们的5-HT1A亲和力。特异性结合常数定义为在生理条件下化合物的质子化物质的受体亲和力。Ki（AH +）的范围为1-3 x 10（-11）M是在5-HT1A受体位点上所研究化合物类别的特定亲和力极限。

  DOI：

  10.1021/jm00091a004

文献信息

• [EN] NOVEL ISOXAZOL DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME, AND A PROCESS FOR THE PREPARATION OF THE NOVEL COMPOUNDS<br/>[FR] NOUVEAUX DERIVES DE L'ISOXAZOLE, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, ET PROCEDE POUR PREPARER LES NOUVEAUX COMPOSES
  申请人：EGIS GYÓGYSZERGYÁR RT.

  公开号：WO1998015541A1

  公开（公告）日：1998-04-16

  (EN) The invention refers to novel isoxazole and 4,5-dihydroisoxazole derivatives of formula (I) being suitable for the treatment of especially a pathological alteration of the central nervous system and/or a cardiovascular and/or gastrointestinal disease, furthermore pharmaceutical compositions containing the above derivatives, and a process for the preparation of the novel compounds. Specifically, the invention refers to isoxazole derivatives of formula (I). In formula (I), A and B represent, independently, a hydrogen atom, or A forms, together with B, a valence bond; Z stands for a hydrogen atom, a halo atom, a C1-4 alkyl group, a trifluoromethyl group or one or two C1-4 alkoxy group(s); R1 and R2 mean, independently, a C1-6 alkyl group or a C3-7 cycloalkyl group; or R1 and R2 form, together with the nitrogen atom they are attached to and optionally with one or more further nitrogen and/or oxygen atom(s), a 5 to 8-membered heterocyclic ring that can be substituted by a C1-4 alkyl group, a (C1-4 alkyl) phenyl group, a (C1-4 alkoxy) phenyl group, a di(C1-4 alkoxy) phenyl group, a halophenyl group, a trifluoromethylphenyl group or a furoyl group; m has a value of 0 or 1; n has a value of 0 or 1.(FR) L'invention concerne de nouveaux dérivés de l'isoxazole et du 4,5-dihydro-isoxazole, de formule (I), convenant pour traiter notamment une altération pathologique du système nerveux central et/ou une maladie cardio-vasculaire et/ou gastro-intestinale, ainsi que des compositions pharmaceutiques contenant lesdits dérivés et un procédé permettant de préparer ces nouveaux composés. Spécifiquement, l'invention concerne des dérivés de l'isoxazole, de formule (I), dans laquelle A et B représentent indépendamment un atome d'hydrogène, ou bien A forme, avec B, une liaison de valence; Z représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle C1-C4, un groupe trifluorométhyle ou bien un ou deux groupe(s) alcoxy C1-C4; R1 et R2 signifient indépendamment un groupe alkyle C1-C6 ou un groupe cycloalkyle C3-C7; ou bien R1 et R2 forment, avec l'atome d'azote sur lequel ils sont fixés et éventuellement avec un ou plusieurs autres atome(s) d'azote et/ou d'oxygène, un noyau hétérocyclique à 5 à 8 éléments qui peut être substitué par un groupe alkyle C1-C4, un groupe (alkyle C1-C4)phényle, un groupe (alcoxy C1-C4)phényle, un groupe di(alcoxy C1-C4)phényle, un groupe halophényle, un groupe trifluorométhyl-phényle ou un groupe furfuroyle; m est 0 ou 1; n est 0 ou 1.
• Structure-activity relationship studies of central nervous system (CNS) agents. 5. Effect of the hydrocarbon chain on the affinity of 4-substituted 1-(3-chlorophenyl)piperazines for 5-HT1A receptor sites
  作者：Jerzy L. Mokrosz、Marzena Pietrasiewicz、Beata Duszynska、Marek T. Cegla

  DOI：10.1021/jm00091a004

  日期：1992.6

  contribute to their 5-HT1A affinity. The specific binding constant was defined as the receptor affinity of the protonated species of compounds under physiological conditions. The range of Ki(AH+) = 1 - 3 x 10(-11) M is a specific affinity limit of the investigated class of compounds at the 5-HT1A receptor sites.

  研究了模型4-取代的1-（3-氯苯基）哌嗪12-31的烃链对其对5-HT1A受体位点的亲和力的影响。发现4-正烷基链的延长强烈增加了所研究化合物的5-HT1A亲和力。正己基衍生物20的亲和力达到最大值（Ki ＝ 2.67nM）。已表明1-芳基哌嗪的N-4取代基的疏水相互作用显着地促进了它们的5-HT1A亲和力。特异性结合常数定义为在生理条件下化合物的质子化物质的受体亲和力。Ki（AH +）的范围为1-3 x 10（-11）M是在5-HT1A受体位点上所研究化合物类别的特定亲和力极限。
• Synthesis and structure–activity relationship of 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives: a novel series of 5-HT2A/2C receptor antagonists. Part 1
  作者：J.Ignacio Andrés、Jesús Alcázar、José M Alonso、Adolfo Dı́az、Javier Fernández、Pilar Gil、Laura Iturrino、Encarna Matesanz、Theo F Meert、Anton Megens、Victor K Sipido

  DOI：10.1016/s0960-894x(01)00721-1

  日期：2002.1

  The synthesis of a series of novel 2-(aminoalkyl)-2,3,3a,8-tetrahydrodibenzo[c,f]isoxazolo[2,3-a]azepine derivatives as well as their 5-HT2A/2C and H-1 receptor binding affinities are described. The in vivo activity as potential anxiolytics of the svnthesised compounds was measured in a mCPP challenge test. One of the compounds, 2a, proved to be a potent 5-HT2A 2C c receptor antagonist showing as well oral activity and therefore could be considered as a potential anxiolytic/antidepressant agent. (C) 2002 Elsevier Science Ltd. All rights reserved.