2-(1-(2,4-dinitrophenyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(1-(2,4-dinitrophenyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
• 英文别名: 2-(1-(2,4-dinitrophenyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl)imidazo[4,5-f][1,10]phenanthroline；2-[1-(2,4-dinitrophenyl)-3-(4-fluorophenyl)pyrazol-4-yl]-1H-imidazo[4,5-f][1,10]phenanthroline
• 化学式: C₂₈H₁₅FN₈O₄
• 分子量: 546.477
• InChiKey: AMNPYDVMDRSMBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-Fluor-acetophenon-<2.4-dinitro-phenylhydrazon> 在 ammonium acetate 、 溶剂黄146 、 三氯氧磷 作用下， 反应 6.0h， 生成 2-(1-(2,4-dinitrophenyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl)-1H-imidazo[4,5-f][1,10]phenanthroline
  参考文献：
  名称：

  Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors

  摘要：

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.03.030

文献信息

• Synthesis and the interaction of 2-(1 H -pyrazol-4-yl)-1 H -imidazo[4,5-f][1,10]phenanthrolines with telomeric DNA as lung cancer inhibitors
  作者：Jiachun Liu、Mei Chen、Yanli Wang、Xiaoyin Zhao、Sijia Wang、Yanling Wu、Wen Zhang

  DOI：10.1016/j.ejmech.2017.03.030

  日期：2017.6

  A novel series of 2-(1H-pyrazol-4-y1)-1H-imidazo[4,5-f][1,101phenanthrolines were designed, synthesized and evaluated for their antitumor activity against lung adenocarcinoma by CCK-8 assay, electrophoretic mobility shift assay (EMSA), UV-melting study, wound healing assay and docking study. These compounds showed good inhibitory activities against lung adenocarcinoma. Especially compound 12c exhibited potential antiproliferative activity against A549 cell line with the half maximal inhibitory concentration (IC50) value of 1.48 mu M, which was a more potent inhibitor than cisplatin (IC50 = 12.08 mu M) and leading compound 2 (IC50 = 1.69 mu M), and the maximum cell inhibitory rate being up to 98.40%. Moreover, further experiments demonstrated that compounds 12a-d can strongly interact with telomeric DNA to stabilize G-quadruplex DNA with increased am values from 12.44 to 20.54 degrees C at a ratio of DNA to compound 1:10. These results implied that growth inhibition of A549 cells mediated by these phenanthroline derivatives is possibly positively correlated to the fact their interaction with telomeric G-quadruplexs. (C) 2017 Elsevier Masson SAS. All rights reserved.