(Z/E)1-(4-methoxyphenyl)-3-(4-((2-oxoindolin-3-ylidene)amino)phenyl)urea

• 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: (Z/E)1-(4-methoxyphenyl)-3-(4-((2-oxoindolin-3-ylidene)amino)phenyl)urea
• 英文别名: 1-(4-methoxyphenyl)-3-[4-[(2-oxo-1H-indol-3-ylidene)amino]phenyl]urea
• 化学式: C₂₂H₁₈N₄O₃
• 分子量: 386.41
• InChiKey: AXIHJSDGKVTVAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  91.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-甲氧基苯基)-3-(4-硝基苯基)脲 在 palladium on activated charcoal 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 (Z/E)1-(4-methoxyphenyl)-3-(4-((2-oxoindolin-3-ylidene)amino)phenyl)urea
  参考文献：
  名称：

  Indoline ureas as potential anti-hepatocellular carcinoma agents targeting VEGFR-2: Synthesis, in vitro biological evaluation and molecular docking

  摘要：

  In our effort to develop potent and effective agents with anti-proliferative activity towards HepG2 hepatocellular carcinoma cells with potential inhibitory activity against VEGFR-2, a novel series of 1-(4-((2oxoindolin-3-ylidene)amino)phenyl)-3-arylureas was designed and synthesized. All the newly prepared ureas 9a-x were evaluated in vitro for their anti-proliferative activity against HepG2 hepatocellular carcinoma cell line. Compounds 9a-c, 9e, 9f, 9j, 9m-o, 9t-v and 9x exhibited good activity against HepG2 cancer cells (IC50 = 1.22 +/- 0.11-8.37 +/- 0.85 mu M) comparable to that of doxorubicin and sorafinib (IC50 = 2.90 +/- 0.36 and 3.40 +/- 0.25 mu M, respectively). These thirteen compounds were further evaluated for their inhibitory activity against VEGFR-2. Compound 9x emerged as the most active counterpart against VEGFR-2 with IC50 value of 031 +/- 0.04 mu M. Furthermore, a molecular docking of the tested compounds was carried out in order to investigate their binding pattern with the prospective target, VEGFR-2 (PDB-code: 4ASD). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.05.040

文献信息

• Indoline ureas as potential anti-hepatocellular carcinoma agents targeting VEGFR-2: Synthesis, in vitro biological evaluation and molecular docking
  作者：Wagdy M. Eldehna、Mohamed Fares、Hany S. Ibrahim、Mohamed H. Aly、Suher Zada、Mamdouh M. Ali、Sahar M. Abou-Seri、Hatem A. Abdel-Aziz、Dalal A. Abou El Ella

  DOI：10.1016/j.ejmech.2015.05.040

  日期：2015.7

  In our effort to develop potent and effective agents with anti-proliferative activity towards HepG2 hepatocellular carcinoma cells with potential inhibitory activity against VEGFR-2, a novel series of 1-(4-((2oxoindolin-3-ylidene)amino)phenyl)-3-arylureas was designed and synthesized. All the newly prepared ureas 9a-x were evaluated in vitro for their anti-proliferative activity against HepG2 hepatocellular carcinoma cell line. Compounds 9a-c, 9e, 9f, 9j, 9m-o, 9t-v and 9x exhibited good activity against HepG2 cancer cells (IC50 = 1.22 +/- 0.11-8.37 +/- 0.85 mu M) comparable to that of doxorubicin and sorafinib (IC50 = 2.90 +/- 0.36 and 3.40 +/- 0.25 mu M, respectively). These thirteen compounds were further evaluated for their inhibitory activity against VEGFR-2. Compound 9x emerged as the most active counterpart against VEGFR-2 with IC50 value of 031 +/- 0.04 mu M. Furthermore, a molecular docking of the tested compounds was carried out in order to investigate their binding pattern with the prospective target, VEGFR-2 (PDB-code: 4ASD). (C) 2015 Elsevier Masson SAS. All rights reserved.