3-[2-(4-苯基哌嗪-1-基)乙基]苯胺 | 1018265-20-7

• 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: 3-[2-(4-苯基哌嗪-1-基)乙基]苯胺
• 英文名称: 3-(2-(4-phenylpiperazin-1-yl)ethyl)aniline
• 英文别名: 3-[2-(4-Phenylpiperazin-1-yl)ethyl]aniline
• CAS: 1018265-20-7
• 化学式: C₁₈H₂₃N₃
• 分子量: 281.401
• InChiKey: FVOUDRKKUVUPRR-UHFFFAOYSA-N

物化性质

• 沸点：
  453.6±40.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-[2-(4-苯基哌嗪-1-基)乙基]苯胺 在 吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.53h， 生成 1-phenyl-3-{3-[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-urea
  参考文献：
  名称：

  Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D2 and 5-hydroxytryptamine 5HT1A receptors

  摘要：

  It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.098
• 作为产物：
  描述：

  3-硝基苯乙酸 在 4-二甲氨基吡啶 、 一水合肼 、 N,N'-二环己基碳二亚胺 、 diborane(6) 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 生成 3-[2-(4-苯基哌嗪-1-基)乙基]苯胺
  参考文献：
  名称：

  Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D2 and 5-hydroxytryptamine 5HT1A receptors

  摘要：

  It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.098

文献信息

• Quinolone-based compounds, formulations, and uses thereof
  申请人：Manetsch Roman

  公开号：US10000452B1

  公开（公告）日：2018-06-19

  Provided herein are quinolone-based compounds that can be used for treatment and/or prevention of malaria and formulations thereof. Also provided herein are methods of treating and/or preventing malaria in a subject by administering a quinolone-based compound or formulation thereof provided herein.

  本文提供了基于喹诺酮的化合物，可用于治疗和/或预防疟疾及其配方。本文还提供了通过给予本文提供的基于喹诺酮的化合物或配方来治疗和/或预防受试者疟疾的方法。
• Design and Synthesis of Orally Bioavailable Piperazine Substituted 4(1<i>H</i>)-Quinolones with Potent Antimalarial Activity: Structure–Activity and Structure–Property Relationship Studies
  作者：Raghupathi Neelarapu、Jordany R. Maignan、Cynthia L. Lichorowic、Andrii Monastyrskyi、Tina S. Mutka、Alexis N. LaCrue、Lynn D. Blake、Debora Casandra、Sherwin Mashkouri、Jeremy N. Burrows、Paul A. Willis、Dennis E. Kyle、Roman Manetsch

  DOI：10.1021/acs.jmedchem.7b00738

  日期：2018.2.22

  develop new antimalarial drugs. Recent in vivo efficacy improvements of the historical antimalarial ICI 56,780 have been reported, however, with the poor solubility and rapid development of resistance, this compound requires further optimization. A series of piperazine-containing 4(1H)-quinolones with greatly enhanced solubility were developed utilizing structure–activity relationship (SAR) and structure–property

  在过去的10至15年中，疟疾死亡人数一直在减少，自2000年以来，全球死亡率下降了47％。尽管世界卫生组织（WHO）建议使用基于青蒿素的联合疗法（ACTs）来对抗疟疾，青蒿素耐药菌株的出现突显了开发新的抗疟药的需要。已经报道了历史上抗疟疾ICI 56,780的近期体内功效改善，但是，由于其较差的溶解度和快速的耐药性，该化合物需要进一步优化。一系列含哌嗪的4（1 H利用结构-活性关系（SAR）和结构-性质关系（SPR）研究开发了溶解度大大提高的喹诺酮类药物。此外，选择了有前途的化合物用于体内筛选研究，以缩小选择范围以进行体内汤普森测试。最后，在常规汤普森试验中，两种含哌嗪的4（1 H）-喹诺酮类药物具有治愈作用，并且还表现出了针对寄生虫肝脏阶段的体内活性。
• [EN] ARYLALKYLPIPERAZINES FOR USE AS NEUROPROTECTIVE AGENTS<br/>[FR] ARYLALKYLPIPÉRAZINES DESTINÉES À ÊTRE UTILISÉES EN TANT QU'AGENTS NEUROPROTECTEURS
  申请人：UNIV HERTFORDSHIRE HIGHER EDUCATION CORP

  公开号：WO2016051155A1

  公开（公告）日：2016-04-07

  A compound of the general formula A or a or a pharmaceutically acceptable salt or solvate thereof, wherein: R1 is selected from the group consisting of: C1-C12-alkyl, C3-C12-cycloalkyl, C6- C10-aryl, and C5-C7-heteroaryl; each optionally substituted with halogen, hydroxyl, OCOR3, amino, C1-C6-alkylamino, C1-C6-dialkylamino, C1C6- (halo)alkyl, C1C6-(halo)- alkoxy and/or COOR3; R2 is selected from the group consisting of: C6-C10-aryl and C5-C7-heteroaryl; each optionally substituted with halogen, hydroxyl, OCOR3 amino, C1C6- alkylamino, CrC6-dialkyl- amino, C1-C6-(halo)alkyl, C1C6-(halo)alkoxy and/or COOR3; R3 is independently at each occurrence selected from the group consisting of hydrogen and C1-C2-alkyl; and n is an integer from 1 to 10 inclusive.

  通式A或其药学上可接受的盐或溶剂的化合物，其中：R1选自以下组合中的一种：C1-C12-烷基，C3-C12-环烷基，C6-C10-芳基和C5-C7-杂芳基；每种均可选择性地取代卤素、羟基、OCOR3、氨基、C1-C6-烷基氨基、C1-C6-二烷基氨基、C1C6-(卤)烷基、C1C6-(卤)烷氧基和/或COOR3；R2选自以下组合中的一种：C6-C10-芳基和C5-C7-杂芳基；每种均可选择性地取代卤素、羟基、OCOR3氨基、C1C6-烷基氨基、CrC6-二烷基氨基、C1-C6-(卤)烷基、C1C6-(卤)烷氧基和/或COOR3；R3在每次出现时独立地选自氢和C1-C2-烷基组合；n为1到10之间的整数（包括1和10）。
• [EN] ARYLPIPERAZINES AS NEUROPROTECTIVE AGENTS<br/>[FR] ARYLPIPÉRAZINES EN TANT QU'AGENTS NEUROPROTECTEURS
  申请人：PROTEOSYS AG

  公开号：WO2012127030A1

  公开（公告）日：2012-09-27

  The present invention generally relates to novel arylpiperazines. In particular, these arylpiperazines can be used as neuroprotective agents. The invention also relates to a process for the manufacture of the novel compounds. Further, the invention relates to the use of the novel arylpiperazines in the treatment of diseases associated with, accompanied by or caused by mitochondrial stress.

  本发明一般涉及新型芳基哌嗪。具体而言，这些芳基哌嗪可用作神经保护剂。本发明还涉及一种制造这些新型化合物的方法。此外，本发明还涉及将这些新型芳基哌嗪用于治疗与、伴随或由线粒体应激引起的疾病的用途。
• ARYLALKYLPIPERAZINES FOR USE AS NEUROPROTECTIVE AGENTS
  申请人：University of Hertfordshire Higher Education Corporation

  公开号：EP3201178B1

  公开（公告）日：2019-10-23