N-(acridin-9-yl)benzamide | 861235-05-4

• 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: N-(acridin-9-yl)benzamide
• 英文别名: 9-benzoylaminoacridine；N-acridin-9-ylbenzamide
• CAS: 861235-05-4
• 化学式: C₂₀H₁₄N₂O
• 分子量: 298.344
• InChiKey: ZXYQARLLWHRPJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(acridin-9-yl)benzamide 、 碘甲烷 在 sodium hydride 作用下， 以 乙腈 、 paraffin oil 为溶剂， 反应 2.5h， 以12%的产率得到N-(acridin-9-yl)-N-methylbenzamide
  参考文献：
  名称：

  S啶的氧化SNH酰胺化和N-（acridin-9-yl）benzamides的互变异构

  摘要：

  a啶分子中氢原子的直接氧化亲核取代反应用于合成9-酰基氨基ac啶。研究了这些化合物的质子型胺亚胺互变异构现象。

  DOI：

  10.1007/s10593-016-1841-7
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.75h， 生成 N-(acridin-9-yl)benzamide
  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.
• Oxidative SNH amidation of acridine and tautomerism of N-(acridin-9-yl)benzamides
  作者：Oleg P. Demidov、Ivan V. Borovlev、Gulminat A. Amangasieva、Elena K. Avakyan

  DOI：10.1007/s10593-016-1841-7

  日期：2016.2

  Direct oxidative nucleophilic substitution of hydrogen atom in acridine molecule was used to synthesize 9-acylaminoacridines. The prototropic amine-imine tautomerism of these compounds was studied.

  a啶分子中氢原子的直接氧化亲核取代反应用于合成9-酰基氨基ac啶。研究了这些化合物的质子型胺亚胺互变异构现象。