(E)-9-methoxy-6-(4-methoxyphenyl)-11H-indeno[1,2-c]quinolin-11-one O-2-(piperidin-1-yl)ethyl oxime | 1352150-47-0

• 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: (E)-9-methoxy-6-(4-methoxyphenyl)-11H-indeno[1,2-c]quinolin-11-one O-2-(piperidin-1-yl)ethyl oxime
• 英文别名: (E)-9-methoxy-6-(4-methoxyphenyl)-N-(2-piperidin-1-ylethoxy)indeno[1,2-c]quinolin-11-imine
• CAS: 1352150-47-0
• 化学式: C₃₁H₃₁N₃O₃
• 分子量: 493.605
• InChiKey: XYWASWNTAYZVBZ-QOSDPKFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-methoxy-6-(4-methoxyphenyl)-11H-indeno[1,2-c]quinolin-11-one 在 盐酸羟胺 、 sodium hydride 作用下， 以 乙二醇乙醚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 (E)-9-methoxy-6-(4-methoxyphenyl)-11H-indeno[1,2-c]quinolin-11-one O-2-(piperidin-1-yl)ethyl oxime
  参考文献：
  名称：

  Synthesis and antiproliferative evaluation of 6-aryl-11-iminoindeno[1,2-c]quinoline derivatives

  摘要：

  A number of 6-aryl-11-iminoindeno[1,2-c]quinoline derivatives were synthesized and evaluated for their antiproliferative activities. Among them, (E)-6-{4-[3-(dimethylamino)propoxy]phenyl}-2-fluoro-9-hydroxy-11H-indeno[1,2-c]quinolin-11-one O-3-(dimethylamino)propyl oxime (23a) was the most active, exhibited GI(50) values of 0.64, 0.39, 0.55, 0.67, and 0.65 mu M against the growth of Hep G2, Hep 3B, A549, H1299, and MDA-MB-231, respectively. Compound 23a inhibited the growth of hepatoma cell lines in a dose-and time-dependent manner. The proportion of cells was decreased in the G1 and accumulated in G2/M phase after 12 h treatment of 23a, while the hypodiploid (sub-G0/G1 phase) cells increased. Further investigations have shown that 23a induced cell cycle arrest at G2/M phase and induce apoptosis via activation of p53, Bax, and caspase-8 which consequently cause cell death. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.014

文献信息

• Synthesis and antiproliferative evaluation of 6-aryl-11-iminoindeno[1,2-c]quinoline derivatives
  作者：Chih-Hua Tseng、Cherng-Chyi Tzeng、Kuin-Yu Chung、Chai-Lin Kao、Chih-Yao Hsu、Chih-Mei Cheng、Keng-Shiang Huang、Yeh-Long Chen

  DOI：10.1016/j.bmc.2011.10.014

  日期：2011.12

  A number of 6-aryl-11-iminoindeno[1,2-c]quinoline derivatives were synthesized and evaluated for their antiproliferative activities. Among them, (E)-6-4-[3-(dimethylamino)propoxy]phenyl}-2-fluoro-9-hydroxy-11H-indeno[1,2-c]quinolin-11-one O-3-(dimethylamino)propyl oxime (23a) was the most active, exhibited GI(50) values of 0.64, 0.39, 0.55, 0.67, and 0.65 mu M against the growth of Hep G2, Hep 3B, A549, H1299, and MDA-MB-231, respectively. Compound 23a inhibited the growth of hepatoma cell lines in a dose-and time-dependent manner. The proportion of cells was decreased in the G1 and accumulated in G2/M phase after 12 h treatment of 23a, while the hypodiploid (sub-G0/G1 phase) cells increased. Further investigations have shown that 23a induced cell cycle arrest at G2/M phase and induce apoptosis via activation of p53, Bax, and caspase-8 which consequently cause cell death. (C) 2011 Elsevier Ltd. All rights reserved.