6-chloro-4-methyl-2-methoxy-N-benzylacridin-9-amine

• 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: 6-chloro-4-methyl-2-methoxy-N-benzylacridin-9-amine
• 英文别名: N-benzyl-6-chloro-2-methoxy-4-methylacridin-9-amine
• 化学式: C₂₂H₁₉ClN₂O
• 分子量: 362.859
• InChiKey: PJYKPFLLBSNHHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-4-甲氧基苯胺 在 铜 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 6-chloro-4-methyl-2-methoxy-N-benzylacridin-9-amine
  参考文献：
  名称：

  Novel synthetic acridine derivatives as potent DNA-binding and apoptosis-inducing antitumor agents

  摘要：

  Acridine derivatives have been explored as DNA-binding anticancer agents. Some derivatives show undesired pharmacokinetic properties and new derivatives need to be explored. In this work, a series of novel acridine analogues were synthesized by modifying previously unexplored linkers between the acridine and benzene groups and their antiproliferative activity and the DNA-binding ability were evaluated. Among these derivatives, compound 5c demonstrated DNA-binding capability and topoisomerase I inhibitory activity. In K562 cell lines, 5c induced apoptosis through mitochondria-dependent intrinsic pathways. These data suggested that compound 5c and other acridine derivatives with modified linkers between the acridine and benzene groups might be potent DNA-binding agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.008

文献信息

• Novel synthetic acridine derivatives as potent DNA-binding and apoptosis-inducing antitumor agents
  作者：Xuliang Lang、Lulu Li、Yuzong Chen、Qinsheng Sun、Qin Wu、Feng Liu、Chunyan Tan、Hongxia Liu、Chunmei Gao、Yuyang Jiang

  DOI：10.1016/j.bmc.2013.05.008

  日期：2013.7

  Acridine derivatives have been explored as DNA-binding anticancer agents. Some derivatives show undesired pharmacokinetic properties and new derivatives need to be explored. In this work, a series of novel acridine analogues were synthesized by modifying previously unexplored linkers between the acridine and benzene groups and their antiproliferative activity and the DNA-binding ability were evaluated. Among these derivatives, compound 5c demonstrated DNA-binding capability and topoisomerase I inhibitory activity. In K562 cell lines, 5c induced apoptosis through mitochondria-dependent intrinsic pathways. These data suggested that compound 5c and other acridine derivatives with modified linkers between the acridine and benzene groups might be potent DNA-binding agents. (C) 2013 Elsevier Ltd. All rights reserved.