1-ethyl-6-fluoro-7-(4-(mesitylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1345888-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-ethyl-6-fluoro-7-(4-(mesitylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Ethyl-6-fluoro-4-oxo-7-[4-(2,4,6-trimethylphenyl)sulfonylpiperazin-1-yl]quinoline-3-carboxylic acid
• CAS: 1345888-40-5
• 化学式: C₂₅H₂₈FN₃O₅S
• 分子量: 501.579
• InChiKey: LZQBNLPENKHGSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,4,6-三甲基苯磺酰氯 、 诺氟沙星 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 1-ethyl-6-fluoro-7-(4-(mesitylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and potential antitumor activity of 7-(4-substituted piperazin-1-yl)-4-oxoquinolines based on ciprofloxacin and norfloxacin scaffolds: in silico studies

  摘要：

  The potential antitumor activities of a series of 7-(4-substituted piperazin-1-yl)fluoroquinolone derivatives (1-14a,b) using ciprofloxacin and norfloxacin as scaffolds are described. These compounds exhibit potent and broad spectrum antitumor activities using 60 human cell lines in addition to the inherent antibacterial activity. Compounds 1a, 2a, 3b, 6b and 7a were found to be the most potent, while 2b, 5b, and 6a were found to have an average activity. The results of this study demonstrated that compounds 1a, 2a, 3b, 6b and 7a (mean GI(50); 2.63-3.09 mu M) are nearly 7-fold more potent compared with the positive control 5-fluorouracil (mean GI(50); 22.60 mu M). More interestingly, compounds 1a, 2a, 3b, 6b and 7a have an almost antitumor activity similar to gefitinib (mean GI(50); 3.24 mu M) and are nearly 2-fold more potent compared to erlotinib (mean GI(50); 7.29 mu M). In silico study and ADME-Tox prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.

  DOI：

  10.3109/14756366.2015.1069288

文献信息

• Design, synthesis and antibacterial activity of fluoroquinolones containing bulky arenesulfonyl fragment: 2D-QSAR and docking study
  作者：Alaa A.-M. Abdel-Aziz、Yousif A. Asiri、Mohamed H.M. Al-Agamy

  DOI：10.1016/j.ejmech.2011.09.011

  日期：2011.11

  Here in, we report the design, synthesis, and antibacterial activity of series of bulky arenesulfonamido derivatives using ciprofloxacin and norfloxacin as scaffolds. All the synthesized compounds were investigated in vitro for their antibacterial activities against two Gram-positive and two Gram-negative organisms using dilution broth method. Among the tested compounds examined, compounds 3-7 showed significance difference from the standard drug ciprofloxacin. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compound 3b into the active site of the topoisomerase II DNA-gyrase enzymes revealed a similar binding mode to ciprofloxacin with additional classical and nonclassical hydrogen bonds. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis and potential antitumor activity of 7-(4-substituted piperazin-1-yl)-4-oxoquinolines based on ciprofloxacin and norfloxacin scaffolds: <i>in silico</i> studies
  作者：Alaa A.-M. Abdel-Aziz、Adel S. El-Azab、Amer M. Alanazi、Yousif A. Asiri、Ibrahim A. Al-Suwaidan、Azza R. Maarouf、Rezk R. Ayyad、Taghreed Z. Shawer

  DOI：10.3109/14756366.2015.1069288

  日期：2016.9.2

  The potential antitumor activities of a series of 7-(4-substituted piperazin-1-yl)fluoroquinolone derivatives (1-14a,b) using ciprofloxacin and norfloxacin as scaffolds are described. These compounds exhibit potent and broad spectrum antitumor activities using 60 human cell lines in addition to the inherent antibacterial activity. Compounds 1a, 2a, 3b, 6b and 7a were found to be the most potent, while 2b, 5b, and 6a were found to have an average activity. The results of this study demonstrated that compounds 1a, 2a, 3b, 6b and 7a (mean GI(50); 2.63-3.09 mu M) are nearly 7-fold more potent compared with the positive control 5-fluorouracil (mean GI(50); 22.60 mu M). More interestingly, compounds 1a, 2a, 3b, 6b and 7a have an almost antitumor activity similar to gefitinib (mean GI(50); 3.24 mu M) and are nearly 2-fold more potent compared to erlotinib (mean GI(50); 7.29 mu M). In silico study and ADME-Tox prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.