1-(4-bromobenzoyl)-4-[4-(2-thienyl)benzoyl]piperazine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-bromobenzoyl)-4-[4-(2-thienyl)benzoyl]piperazine
• 英文别名: [4-(4-Bromobenzoyl)piperazin-1-yl]-(4-thiophen-2-ylphenyl)methanone；[4-(4-bromobenzoyl)piperazin-1-yl]-(4-thiophen-2-ylphenyl)methanone
• 化学式: C₂₂H₁₉BrN₂O₂S
• 分子量: 455.375
• InChiKey: BFSMWDPRHAHFSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-羧基苯硼酸 在 四(三苯基膦)钯 、 caesium carbonate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 72.0h， 生成 1-(4-bromobenzoyl)-4-[4-(2-thienyl)benzoyl]piperazine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel aromatic-heterocyclic biphenyls as potent anti-leukemia agents

  摘要：

  As a continuation to our previous research, twenty-eight aromatic-heterocyclic biphenyls were designed and synthesized as novel Bcr-Abl inhibitors. The title compounds were investigated for their anti-proliferative activities against wild K562 cells and Imatinib-resistant K562 cells (K562R). The results indicated that most of them exhibited potent Bcr-Abl inhibition and moderate antiproliferative potency against K562 cells. Furthermore, three compounds 3, 7 and 21 displayed moderate antiproliferative activities against K562R cells. Molecular docking indicated that 3 bound more tightly with Bcr-Abl(T315I) compared to Bcr-Abl(WT). The higher affinity was consistent with its relatively promising K562R cell growth inhibition. These aromatic-heterocyclic biphenyls could be considered as novel lead compound for optimized as Bcr-Abl(T315I) inhibitors. They provide a good starting point for the further development of novel anti-leukemia agents capable of dealing with clinical acquired resistance against Imatinib. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.015

文献信息

• Synthesis and biological evaluation of novel aromatic-heterocyclic biphenyls as potent anti-leukemia agents
  作者：Jinyun Dong、Xiaoyan Pan、Jinfeng Wang、Ping Su、Lin Zhang、Fen Wei、Jie Zhang

  DOI：10.1016/j.ejmech.2015.07.015

  日期：2015.8

  As a continuation to our previous research, twenty-eight aromatic-heterocyclic biphenyls were designed and synthesized as novel Bcr-Abl inhibitors. The title compounds were investigated for their anti-proliferative activities against wild K562 cells and Imatinib-resistant K562 cells (K562R). The results indicated that most of them exhibited potent Bcr-Abl inhibition and moderate antiproliferative potency against K562 cells. Furthermore, three compounds 3, 7 and 21 displayed moderate antiproliferative activities against K562R cells. Molecular docking indicated that 3 bound more tightly with Bcr-Abl(T315I) compared to Bcr-Abl(WT). The higher affinity was consistent with its relatively promising K562R cell growth inhibition. These aromatic-heterocyclic biphenyls could be considered as novel lead compound for optimized as Bcr-Abl(T315I) inhibitors. They provide a good starting point for the further development of novel anti-leukemia agents capable of dealing with clinical acquired resistance against Imatinib. (C) 2015 Elsevier Masson SAS. All rights reserved.