7-(4-((4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenylcarbamoyl)-methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 7-(4-((4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenylcarbamoyl)-methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-4-oxo-7-[4-[2-oxo-2-[4-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]anilino]ethyl]piperazin-1-yl]quinoline-3-carboxylic acid
• 化学式: C₃₇H₃₇FN₄O₈
• 分子量: 684.721
• InChiKey: KIEMZWYZHOUAKS-NYYWCZLTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  50
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (E)-1-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 7-(4-((4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenylcarbamoyl)-methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity

  摘要：

  A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI(50) level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 gI A and 20 mu M concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 RM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 laM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a j compared to the parent ciprofloxacin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.040

文献信息

• Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase I and II inhibitory activity
  作者：Mohamed Abdel-Aziz、So-Eun Park、Gamal El-Din A.A. Abuo-Rahma、Mohamed A. Sayed、Youngjoo Kwon

  DOI：10.1016/j.ejmech.2013.08.040

  日期：2013.11

  A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI(50) level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 gI A and 20 mu M concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 RM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 laM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a j compared to the parent ciprofloxacin. (C) 2013 Elsevier Masson SAS. All rights reserved.