2-Bromo-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone | 1185180-70-4

• 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: 2-Bromo-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone
• 英文别名: 2-bromo-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone
• CAS: 1185180-70-4
• 化学式: C₁₂H₁₃BrCl₂N₂O
• 分子量: 352.058
• InChiKey: LZBRWZONJVYYLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(氯甲基)-4,5-二甲氧基-2-硝基苯 、 2-Bromo-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到1-[4-(3,4-dichlorophenyl)piperazin-1-yl]-3-(4,5-dimethoxy-2-nitrophenyl)propan-1-one
  参考文献：
  名称：

  Original TDAE strategy using α-halocarbonyl derivatives

  摘要：

  We report herein the selective C-C bond formation by the reaction of nitrobenzyl carbanions, formed via the TDAE strategy. with alpha-haloesters and alpha-haloamides. This reaction, extended in benzodioxole and dimethoxybenzene series provides new potentially CNS active agents. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.036
• 作为产物：
  描述：

  溴乙酸 、 1-(3,4-二氯苯基)哌嗪 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Bromo-1-[4-(3,4-dichlorophenyl)piperazin-1-yl]ethanone
  参考文献：
  名称：

  Synthesis, molecular docking and biological evaluation of coumarin derivatives containing piperazine skeleton as potential antibacterial agents

  摘要：

  A series of 4-hydroxycoumarin derivatives were designed and synthesized in order to find some more potent antibacterial drugs. Their antibacterial activities against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus were tested. These compounds showed good antibacterial activities against Gram-positive strains. Compound 4g represented the most potent antibacterial activity against Bacillus subtilis and S. aureus with MIC of 0.236, 0.355 mu g/mL, respectively. What's more, it showed the most potent activity against SaFabI with IC50 of 0.57 mu M. Molecular docking of 4g into S. aureus Enoyl-ACP-reductase active site were performed to determine the probable binding mode, while the QSAR model was built to check the previous work as well as to introduce new directions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.048

文献信息

• New orally effective 3-(2-nitro)phenylpropanamide analgesic derivatives: Synthesis and antinociceptive evaluation
  作者：Marc Since、Thomas Freret、Gerald Nee、Thierry Terme、Patrice Vanelle、Michel Boulouard

  DOI：10.1016/j.ejmech.2013.08.041

  日期：2013.11

  A series of substituted 6-nitrophenylpropanamide derivatives (1-20) were synthesized using either the TDAE strategy or classical organic reactions. All these compounds were characterized by fusion point, 1H NMR,13C NMR, elemental analysis or mass spectrometry data. Because of their structural analogy with recently published compounds possessing antinociceptive properties, our derivatives were screened for peripheral analgesic activities on acetic acid-induced writhing in mice. Compound 13 showed the best result at 100 junol/kg ip (50% inhibition vs 59% for aspirin). This antinociceptive activity was maintained after oral administration (40% inhibition vs 31.6% for aspirin). Both hot-plate and actimetry-based tests were non-significant suggesting the analgesic activity of 13 linked to a peripheral mechanism. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis, molecular docking and biological evaluation of coumarin derivatives containing piperazine skeleton as potential antibacterial agents
  作者：She-Feng Wang、Yong Yin、Xun Wu、Fang Qiao、Shao Sha、Peng-Cheng Lv、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2014.09.048

  日期：2014.11

  A series of 4-hydroxycoumarin derivatives were designed and synthesized in order to find some more potent antibacterial drugs. Their antibacterial activities against Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus were tested. These compounds showed good antibacterial activities against Gram-positive strains. Compound 4g represented the most potent antibacterial activity against Bacillus subtilis and S. aureus with MIC of 0.236, 0.355 mu g/mL, respectively. What's more, it showed the most potent activity against SaFabI with IC50 of 0.57 mu M. Molecular docking of 4g into S. aureus Enoyl-ACP-reductase active site were performed to determine the probable binding mode, while the QSAR model was built to check the previous work as well as to introduce new directions. (C) 2014 Elsevier Ltd. All rights reserved.
• Original TDAE strategy using α-halocarbonyl derivatives
  作者：Marc Since、Thierry Terme、Patrice Vanelle

  DOI：10.1016/j.tet.2009.05.036

  日期：2009.8

  We report herein the selective C-C bond formation by the reaction of nitrobenzyl carbanions, formed via the TDAE strategy. with alpha-haloesters and alpha-haloamides. This reaction, extended in benzodioxole and dimethoxybenzene series provides new potentially CNS active agents. (C) 2009 Elsevier Ltd. All rights reserved.