4-(2-(4-(4-chlorophenyl)piperazin-1-yl)-2-oxoethoxy)-2H-chromen-2-one

• 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-(2-(4-(4-chlorophenyl)piperazin-1-yl)-2-oxoethoxy)-2H-chromen-2-one
• 英文别名: 4-(2-(4-(4-chlorophenyl)piperazin-1-yl)-2-oxoethoxy)-2H-benzopyran-2-one；4-[2-[4-(4-Chlorophenyl)piperazin-1-yl]-2-oxoethoxy]chromen-2-one；4-[2-[4-(4-chlorophenyl)piperazin-1-yl]-2-oxoethoxy]chromen-2-one
• 化学式: C₂₁H₁₉ClN₂O₄
• 分子量: 398.846
• InChiKey: SBHDWOLKRFPQBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)哌嗪 在 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-(4-(4-chlorophenyl)piperazin-1-yl)-2-oxoethoxy)-2H-chromen-2-one
  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

• 含哌嗪环的香豆素类衍生物及其制备与在抗菌药物中的应用
  申请人：南京大学

  公开号：CN105218501A

  公开（公告）日：2016-01-06

  含哌嗪环的香豆素类衍生物，它具有如下通式。实验证明，含哌嗪环的香豆素类衍生物对革兰氏阳性菌金黄色葡萄球菌(S.aureus)和枯草芽孢杆菌(B.subtilis)有一定的抑制作用，而对革兰氏阴性菌铜绿假单胞(P.aeruginosa)和大肠杆菌(E.coli)几乎没有抑制作用。因此它们有可能用于制备抗菌的药物。本发明公开了含哌嗪环的香豆素类衍生物的制法。其中R1，R2分别如图所示。
• 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.