2-[4-[2-(1-piperidyl)ethoxy]phenyl]-1H-imidazo[4,5-f]-1,10-phenanthroline | 1352326-98-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[4-[2-(1-piperidyl)ethoxy]phenyl]-1H-imidazo[4,5-f]-1,10-phenanthroline
• 英文别名: 2-[4-(2-piperidin-1-ylethoxy)phenyl]-1H-imidazo[4,5-f][1,10]phenanthroline
• CAS: 1352326-98-7
• 化学式: C₂₆H₂₅N₅O
• 分子量: 423.517
• InChiKey: ONDYNEOXKHBNBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-hydroxyphenyl)imidazo[4,5-f][1,10]phenanthroline 、 1-(2-氯乙基)哌啶盐酸盐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 73.5h， 以29%的产率得到2-[4-[2-(1-piperidyl)ethoxy]phenyl]-1H-imidazo[4,5-f]-1,10-phenanthroline
  参考文献：
  名称：

  4-(1H-Imidazo[4,5-f]-1,10-phenanthrolin-2-yl)phenol-based G-quadruplex DNA binding agents: Telomerase inhibition, cytotoxicity and DNA-binding studies

  摘要：

  Four novel 4-(1H-imidazo[4,5-f]-1,10-phenanthrolin-2-yl)phenol derivatives 1-4 have been synthesized, and their G-quadruplex DNA-binding interactions, telomerase inhibition, antiproliferative activity, cell cycle arrest, and apoptotic induction were studied. All compounds show the preferential h-telo, c-myc, and c-kit2 G-quadruplex binding affinity and the G-quadruplex versus duplex selectivity. In the case of the same G-quadruplex target, the compound 1 exhibits better stabilization effect (Lambda T-m) than the other three compounds and also gives 80.2% inhibition of telomerase activity at 7.5 mu M. All compounds can promote selectively the formation of parallel G-quadruplex structure of both c-myc and c-kit2 without addition of any cations. Four compounds display the cytotoxicity activities against HeLa and HepG2 cells by MTT assay with IC50 values of about 10(-6) and 10(-5) M, respectively, and cause a substantial decrease in the G(2)/M-phase cell population and a significant increase in the number of apoptotic cells. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.059

文献信息

• 4-(1H-Imidazo[4,5-f]-1,10-phenanthrolin-2-yl)phenol-based G-quadruplex DNA binding agents: Telomerase inhibition, cytotoxicity and DNA-binding studies
  作者：Chun-Ying Wei、Jun-Hong Wang、Ye Wen、Jie Liu、Li-Hua Wang

  DOI：10.1016/j.bmc.2012.11.059

  日期：2013.6

  Four novel 4-(1H-imidazo[4,5-f]-1,10-phenanthrolin-2-yl)phenol derivatives 1-4 have been synthesized, and their G-quadruplex DNA-binding interactions, telomerase inhibition, antiproliferative activity, cell cycle arrest, and apoptotic induction were studied. All compounds show the preferential h-telo, c-myc, and c-kit2 G-quadruplex binding affinity and the G-quadruplex versus duplex selectivity. In the case of the same G-quadruplex target, the compound 1 exhibits better stabilization effect (Lambda T-m) than the other three compounds and also gives 80.2% inhibition of telomerase activity at 7.5 mu M. All compounds can promote selectively the formation of parallel G-quadruplex structure of both c-myc and c-kit2 without addition of any cations. Four compounds display the cytotoxicity activities against HeLa and HepG2 cells by MTT assay with IC50 values of about 10(-6) and 10(-5) M, respectively, and cause a substantial decrease in the G(2)/M-phase cell population and a significant increase in the number of apoptotic cells. (C) 2012 Elsevier Ltd. All rights reserved.