4-(4-(2-chlorophenyl)piperazin-1-yl)aniline | 75291-16-6

• 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: 4-(4-(2-chlorophenyl)piperazin-1-yl)aniline
• 英文别名: 4-[4-(2-chlorophenyl)piperazin-1-yl]phenylamine；1-(o-Chlorophenyl)-4-[(4-aminophenyl)]piperazine；4-[4-(2-chlorophenyl)piperazin-1-yl]aniline
• CAS: 75291-16-6
• 化学式: C₁₆H₁₈ClN₃
• 分子量: 287.792
• InChiKey: QQZMIVRUPVSSTO-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  488.7±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 4-(4-(2-chlorophenyl)piperazin-1-yl)aniline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到N-{4-[4-(2-chlorophenyl)piperazin-1-yl]phenyl}carbamic acid ethyl ester
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of new arylpiperazines N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives: Putative role of 5-HT1A receptors

  摘要：

  In an attempt to design novel 5-HT1A agonists/partial agonists, based on an arylpiperazine nucleus, a series of N-{4-[4-(aryl) piperazine-1-yl]-phenyl}-amine derivatives were synthesized and biologically tested. The anxiolytic effect of the compounds was investigated employing the Elevated plus Maze (EPM) task. On the basis of in vivo functional test, compound 1c (3 mg/kg) and 4c (3 mg/kg) induced significant increments in open arm entries and time on EPM as compared to Buspirone. The anxiolytic effects of compounds 1c and 4c were effectively antagonized by WAY-100635, a 5-HT1A receptor antagonist (0.5 mg/kg). Furthermore, we have also evaluated the concentration of 5-HT in the brain tissue using HPLC with fluorescent detection. Our result showed that serotonin levels were significantly decreased by similar to 38% (p < 0.001) and similar to 32% (p < 0.001) after acute administration of compounds 1c and 4c, respectively. These findings suggest that the anxiolytic like activity of these new arylpiperazines is mediated via 5-HT1A receptors in the brain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.043
• 作为产物：
  描述：

  1-(2-chlorophenyl)-4-(4-nitrophenyl)piperazine 在 盐酸 、 tin 作用下， 以94 %的产率得到4-(4-(2-chlorophenyl)piperazin-1-yl)aniline
  参考文献：
  名称：

  强效新合成乙酰胆碱酯酶抑制剂的结构活性和结合方向分析

  摘要：

  在基于配体的药物设计方法中，合成了十四种新型N-苄基哌啶和N,N-二芳基哌嗪偶联物，并作为多奈哌齐类似物进行了药理学评估。所有化合物都具有高到中度的体外抑制活性，IC 50在 2.3–20 µM 范围内，并且对乙酰胆碱酯酶具有选择性，同时对丁酰胆碱酯酶没有活性。构效关系分析揭示了N,N-二芳基哌嗪部分和连接两个药效团的接头对抑制活性的影响。两种最活跃的化合物7g和8g的动力学研究(IC 50 = 2.3 和 4 µM，分别）揭示了混合型抑制模式，与游离酶和酶-底物复合物结合。为了进一步了解作用机制和结合方向，对所有化合物进行了分子对接，同时对7g和8g进行了配体转运模拟和分子动力学模拟。计算结果很好地证实了体外活性和动力学研究。

  DOI：

  10.1016/j.molstruc.2022.134809

文献信息

• New Quinolines as Potential CNS Agents
  作者：Garima Sathi、Vibha R. Gujrati、Manju Sharma、Chandishwar Nath、Krishna P. Bhargava、Kirpa Shanker

  DOI：10.1002/ardp.19833160908

  日期：——

  aryl‐1‐(4‐aminophenyl)piperazines and substituted piperidines with substituted 4‐chloroquinolines. The compounds were screened for their monoamine oxidase (MAO) inhibitory activities (in vitro) and various CNS activities (in vivo). Some compounds showed promising MAO inhibitory and antidepressant activities. The compounds did not produce acute neurological deficits and have low toxicity. Compound 1b is the

  化合物1a-1l和2a-2m是通过各种芳基-1-（4-氨基苯基）哌嗪和取代哌啶与取代4-氯喹啉缩合合成的。筛选化合物的单胺氧化酶 (MAO) 抑制活性（体外）和各种 CNS 活性（体内）。一些化合物显示出有希望的 MAO 抑制和抗抑郁活性。这些化合物不会产生急性神经功能缺损并且具有低毒性。化合物 1b 是该系列中最活跃的成员。讨论了结构-活性关系。
• Piperazino methyl phenyl aminoquinolines
  申请人：The Upjohn Company

  公开号：US04140775A1

  公开（公告）日：1979-02-20

  Antihypertensive compounds of the formula III ##STR1## wherein X is chloro or trifluoromethyl; wherein R is hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R.sub.1 is phenyl or phenyl substituted with one or two alkyl, alkoxy, trifluoromethyl or halo substituents, in which alkyl and alkoxy are each of 1 to 3 carbon atoms, inclusive, and halo is fluoro, chloro or bromo, are prepared by reacting a 4-chloro-7-substituted quinoline of formula I with a compound of the formula II ##STR2## wherein R and R.sub.1 are defined as above. The pharmacologically acceptable acid addition salts of compounds of formula III can also be used as antihypertensive agents.

  公式III的降压化合物为##STR1## 其中X为氯或三氟甲基；其中R为氢或1至3个碳原子的烷基；其中R.sub.1为苯基或被一或两个烷基，烷氧基，三氟甲基或卤素取代的苯基，其中烷基和烷氧基均为1至3个碳原子，卤素为氟，氯或溴。所述化合物通过将公式I的4-氯-7-取代喹啉与公式II的化合物反应而制备。公式III化合物的药学上可接受的酸盐也可用作降压剂。
• SATHI, G.;GUJRATI, V. R.;SHARMA, M.;NATH, C.;BHARGAVA, K. P.;SHANKER, K., ARCH. PHARM., 1983, 316, N 9, 767-772
  作者：SATHI, G.、GUJRATI, V. R.、SHARMA, M.、NATH, C.、BHARGAVA, K. P.、SHANKER, K.

  DOI：——

  日期：——
• US4140775A
  申请人：——

  公开号：US4140775A

  公开（公告）日：1979-02-20