5-methoxy-N-(2-methoxyethyl)-9-oxo-1-((pyridin-3-ylmethyl)amino)-9,10-dihydroacridine-4-carboxamide

• 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: 5-methoxy-N-(2-methoxyethyl)-9-oxo-1-((pyridin-3-ylmethyl)amino)-9,10-dihydroacridine-4-carboxamide
• 英文别名: 5-methoxy-N-(2-methoxyethyl)-9-oxo-1-(pyridin-3-ylmethylamino)-10H-acridine-4-carboxamide
• 化学式: C₂₄H₂₄N₄O₄
• 分子量: 432.479
• InChiKey: GYTGAAKCWHUMSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基-3-甲氧基苯甲酸 在 硫酸 、 铜 、 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 5-methoxy-N-(2-methoxyethyl)-9-oxo-1-((pyridin-3-ylmethyl)amino)-9,10-dihydroacridine-4-carboxamide
  参考文献：
  名称：

  Molecular design, synthesis and biological research of novel pyridyl acridones as potent DNA-binding and apoptosis-inducing agents

  摘要：

  A series of novel pyridyl acridone derivatives comprised of a pseudo-five-cyclic system to extend the pi-conjugated acridone chromophore, were designed and synthesized as potent DNA binding antitumor compounds. Most synthesized compounds displayed good activity against human leukemia K562 cells in MU tests, with compound 6d exhibiting the highest activity with IC50 value at 0.46 mu M. Moreover, 6d showed potent activities against solid tumor cell lines (0.16-3.79 mu M). Several experimental studies demonstrated that the antitumor mode of action of compound 6d involves DNA intercalation, topoisomerase I inhibition, and apoptosis induction through the mitochondrial pathway. In summary, compound 6d represents a novel and promising lead structure for the development of new potent anticancer DNA-binding agents. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.003

文献信息

• Molecular design, synthesis and biological research of novel pyridyl acridones as potent DNA-binding and apoptosis-inducing agents
  作者：Bin Zhang、Kang Chen、Ning Wang、Chunmei Gao、Qinsheng Sun、Lulu Li、Yuzong Chen、Chunyan Tan、Hongxia Liu、Yuyang Jiang

  DOI：10.1016/j.ejmech.2015.02.003

  日期：2015.3

  A series of novel pyridyl acridone derivatives comprised of a pseudo-five-cyclic system to extend the pi-conjugated acridone chromophore, were designed and synthesized as potent DNA binding antitumor compounds. Most synthesized compounds displayed good activity against human leukemia K562 cells in MU tests, with compound 6d exhibiting the highest activity with IC50 value at 0.46 mu M. Moreover, 6d showed potent activities against solid tumor cell lines (0.16-3.79 mu M). Several experimental studies demonstrated that the antitumor mode of action of compound 6d involves DNA intercalation, topoisomerase I inhibition, and apoptosis induction through the mitochondrial pathway. In summary, compound 6d represents a novel and promising lead structure for the development of new potent anticancer DNA-binding agents. (C) 2015 Elsevier Masson SAS. All rights reserved.