1-(4-氯邻甲苯)哌嗪 | 58820-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 1-(4-氯邻甲苯)哌嗪
• 英文名称: 1-(4-Chloro-2-methylphenyl)-piperazine
• 英文别名: 1-(4-Chloro-o-tolyl)piperazine；1-(4-chloro-2-methylphenyl)piperazine
• CAS: 58820-36-3
• 化学式: C₁₁H₁₅ClN₂
• 分子量: 210.706
• InChiKey: MXEFOSLEAQWWDM-UHFFFAOYSA-N

物化性质

• 沸点：
  350.4±42.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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-(4-氯邻甲苯)哌嗪 在 aluminium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 trans-1-[(2-phenylcyclopropyl)methyl]-4-(4-chloro-2-methylphenyl)piperazine
  参考文献：
  名称：

  trans-1-[(2-Phenylcyclopropyl)methyl]-4-arylpiperazines:  Mixed Dopamine D₂/D₄ Receptor Antagonists as Potential Antipsychotic Agents

  摘要：

  The dopaminergic receptor profile of a series of trans-1-[(2-phenylcyclopropyl)methyl]-4-arylpiperazines was examined. Aromatic substitution patterns were varied with the goal of identifying a compound having affinities for the D-2 and D-4 receptors in a ratio similar to that observed for the atypical neuroleptic clozapine. The compounds (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine (5m) and (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine (5t) were selected for functional antagonists at D-2 and D-4 receptors and had a D-2/D-4 ratio approximating that of clozapine; they proved inactive in behavioral tests of antipsychotic activity.

  DOI：

  10.1021/jm990562x
• 作为产物：
  描述：

  4-(4-chloro-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(4-氯邻甲苯)哌嗪
  参考文献：
  名称：

  CHEMOKINE RECEPTOR ANTAGONISTS AND METHODS OF USE THEREOF

  摘要：

  揭示了新颖的化合物以及治疗与异常白细胞召集和/或激活相关的疾病的方法。该方法包括向需要的受试者施用代表的化合物的有效量： 或其生理上可接受的盐。

  公开号：

  US20160031908A1
• 作为试剂：
  描述：

  N-{3-[4-(4-Fluoro-2-methylphenyl)-1-piperazinyl]-propyl}-5-methyl-3-phenylisoxazole-4-carboxamide 、 4-氯-2-甲基苯胺 在 1-(4-氯邻甲苯)哌嗪 、 氯仿 、 甲醇 作用下， 以afforded the title compound (73%) as an oil的产率得到1-(4-氯邻甲苯)哌嗪
  参考文献：
  名称：

  Isoxazolecarboxamide derivatives

  摘要：

  本发明涉及新型N-(取代苯基)-N′-[ω-(3-取代苯基-4-异噁唑甲酰胺基)烷基]哌嗪化合物及其N-氧化物和药物可接受的盐。这些化合物具有增强的α1-肾上腺素受体选择性和降低血压的低活性。这些化合物在治疗下尿路梗阻综合征，包括良性前列腺增生症(BPH)，以及治疗下尿路症状(LUTS)和神经源性下尿路功能障碍(NLUTD)等疾病方面具有用途。这些化合物可以单独或与抗胆碱药物联合使用。

  公开号：

  US06680319B2

文献信息

• Practical Method for Parallel Synthesis of Diversely Substituted 1- henylpiperazines
  作者：Igor Konstantinov、Konstantin Bukhryakov、Yuri Gezentsvey、Mikhail Krasavin

  DOI：10.2174/157017811799304386

  日期：2011.11.1

  A simple and practical method to prepare ‘libraries’ of substituted 1-phenylpiperazine building blocks in parallel format has been developed.

  已经开发出一种简单实用的方法，用于制备以替代1-苯基哌嗪构建块为内容的“库”，采用并行格式。
• Chemokine receptor antagonists and methods of use thereof
  申请人：Luly R. Jay

  公开号：US20050070549A1

  公开（公告）日：2005-03-31

  Disclosed are novel compounds and a method of treating a disease associated with aberrant leukocyte recruitment and/or activation. The method comprises administering to a subject in need an effective amount of a compound represented by: formula (1) or physiologically acceptable salt thereof.

  揭示了新化合物和一种治疗与异常白细胞召集和/或激活相关疾病的方法。该方法包括向需要的受试者施用由以下公式（1）表示的化合物或其生理上可接受的盐的有效量。
• Piperazine Derivatives of Dialkyl Oxindoles
  申请人：Volk Balazs

  公开号：US20070232619A1

  公开（公告）日：2007-10-04

  The present invention is concerned with new 3,3-disubstituted indol-2-one derivatives of the general Formula (I), wherein R 1 stands for hydrogen, halogen, alkyl having 1-7 carbon atom(s) or sulfonamido; R 2 represents hydrogen or halogen; R 3 denotes hydrogen, alkyl having 1-7 carbon atom(s) optionally carrying an aryl substituent or aryl optionally carrying one or two halogen substituent(s); R 4 stands for alkyl having 1-7 carbon atom(s); R 5 represents a group of the general Formula (II a) or (II b), wherein Q and W each represents nitrogen or CH; R 6 , R 7 and R 8 each stands for hydrogen, halogen, trifluoromethyl, alkyl or alkoxy having 1-7 carbon atom(s), or R 6 and R 7 together represent ethylenedioxy; m is 0, 1, or 2; a is a single, double or triple bond; n is 0, 1 or 2; and pharmaceutically acceptable acid addition salts thereof which are useful in the treatment or prophylaxis of diseases of the central nervous system, the gastrointestinal system and the cardiovascular system.

  本发明涉及一般式（I）的新的3,3-二取代吲哚-2-酮衍生物，其中R1代表氢、卤素、具有1-7个碳原子的烷基或磺胺基；R2代表氢或卤素；R3代表氢、具有1-7个碳原子的烷基，可选地带有芳基取代基，或芳基，可选地带有一个或两个卤素取代基；R4代表具有1-7个碳原子的烷基；R5代表一般式（II a）或（II b）的基团，其中Q和W各自代表氮或CH；R6、R7和R8各自代表氢、卤素、三氟甲基、具有1-7个碳原子的烷基或烷氧基，或R6和R7一起代表乙二氧基；m为0、1或2；a为单键、双键或三键；n为0、1或2；以及其药学上可接受的酸盐，用于治疗或预防中枢神经系统、消化系统和心血管系统疾病。
• 2-((4-Arylpiperazin-1-yl)methyl)benzonitrile Derivatives as Orally Available Inhibitors of Hepatitis C Virus with a Novel Mechanism of Action
  作者：Xinbei Jiang、Jiali Tan、Yixuan Wang、Jinhua Chen、Jianrui Li、Zhi Jiang、Yanni Quan、Jie Jin、Yuhuan Li、Shan Cen、Yanping Li、Zonggen Peng、Zhuorong Li

  DOI：10.1021/acs.jmedchem.0c00232

  日期：2020.6.11

  reach the elimination of HCV in the absence of a vaccine. 4-(Piperazin-1-yl)-2-((p-tolylamino)methyl)-benzonitrile (1) is a modest HCV inhibitor identified from an in-house screening using a HCV-infected Huh7.5 cell culture. Starting from it, the chemical optimization afforded a new 2-((4-arylpiperazin-1-yl)methyl)benzonitrile scaffold with significantly increased antiviral activity against HCV. A highly

  尽管直接作用的抗病毒药物在过去十年中彻底改变了丙型肝炎病毒（HCV）的感染治疗方法，但在没有疫苗的情况下，需要更多的努力来消除HCV。4-（哌嗪-1-基）-2-（（对甲苯基氨基）甲基）-苯甲腈（1）是一种中等的HCV抑制剂，可通过使用HCV感染的Huh7.5细胞培养物进行的内部筛选确定。从其开始，化学优化提供了新的2-（（4-芳基哌嗪-1-基）甲基）苄腈支架，其对HCV的抗病毒活性显着提高。通过结构-活性关系研究确定了一种高效的HCV抑制剂35（L0909，EC 50 = 0.022μM，SI> 600）。生物学研究表明，L0909可以通过在HCV进入阶段采取行动来阻止HCV复制。对于该化合物，观察到了对临床耐药HCV突变株的高敏感性以及与临床药物的协同作用。进一步的药物研究表明，L0909具有持久性，可以口服，并且体内毒性低。这些结果表明，L0909是有前途的HCV进入抑制剂，可用于单一或联合治疗。
• Antivertigo agents. I. Structure-activity relationships of 2-(2-aminoethyl)pyridines.
  作者：AKIRA SHIOZAWA、YUHICHIRO ICHIKAWA、CHIKARA KOMURO、GENICHI IDZU、MICHIO ISHIKAWA、SHUJI KURASHIGE、HIROSHI MIYAZAKI、HIROSHI YAMANAKA、TAKAO SAKAMOTO

  DOI：10.1248/cpb.32.553

  日期：——

  A series of 2-(2-aminoethyl) pyridines derived by the modification of the amine moiety in betahistine, 2-(2-methylaminoethyl) pyridine, was synthesized and evaluated for antivertigo action in terms of inhibitory activity against spontaneous nystagmus in cats. The structure-activity relationships between the amine moieties and antivertigo activities were investigated. The effects of substituents on the phenyl ring of the 4-phenylpiperazine moiety were investigated by means of quantitative regression analysis using various physicochemical parameters. The following equation gave the best correlation. log 1/ID30=-0.417 (±0.322) π+0.166 (±0.048) MR-1.473 (±0.237) (n=15, s=0.239, r=0.910, F212=28.887). In this series of compounds, 1-(2-methoxyphenyl)-4-[2-(2-pyridyl) ethyl] piperazine, 1-(2-methoxyphenyl)-4-[2-[2-(6-methyl) pyridyl] ethyl]-piperazine, and 1-(2-methoxyphenyl)-4-[2-[2-(5-ethyl) pyridyl] ethyl] piperazine were found to show more potent activity than betahistine. Thus, the 4-(2-methoxyphenyl) piperazine group was found to be the most effective amine moiety for activity against spontaneous nystagmus.

  通过修改倍他司汀中的胺部分，合成了一系列2-(2-氨基乙基)吡啶，并将其合成的2-(2-甲基氨基乙基)吡啶，就其对猫自发性眼球震颤的抑制活性，评估了它们的抗眩晕作用。研究了胺部分与抗眩晕活性之间的构效关系。通过利用各种物理化学参数进行定量回归分析，研究了4-苯基哌嗪部分苯环上取代基的影响。以下方程给出了最佳相关性。log 1/ID30=-0.417 (±0.322) π+0.166 (±0.048) MR-1.473 (±0.237) (n=15, s=0.239, r=0.910, F212=28.887).在这一系列化合物中，发现1-(2-甲氧基苯基)-4-[2-(2-吡啶基)乙基]哌嗪，1-(2-甲氧基苯基)-4-[2-[2-(6-甲基)吡啶基]乙基]-哌嗪，和1-(2-甲氧基苯基)-4-[2-[2-(5-乙基)吡啶基]乙基]哌嗪的活性强于倍他司汀。因此，发现4-(2-甲氧基苯基)哌嗪部分是对抗自发性眼球震颤活性最有效的胺部分。