N-[4-(4-nitrobenzamido)butyl]-9-chloroacridine-4-carboxamide | 455251-68-0

• 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-[4-(4-nitrobenzamido)butyl]-9-chloroacridine-4-carboxamide
• 英文别名: 9-chloro-N-[4-[(4-nitrobenzoyl)amino]butyl]acridine-4-carboxamide
• CAS: 455251-68-0
• 化学式: C₂₅H₂₁ClN₄O₄
• 分子量: 476.919
• InChiKey: NGKAOQZJUXBULQ-UHFFFAOYSA-N

物化性质

• 沸点：
  813.1±55.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  114.23
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-amino-9-(10-amino-3,7-diazadecyl)-9H-purine 、 N-[4-(4-nitrobenzamido)butyl]-9-chloroacridine-4-carboxamide 在 三乙胺 作用下， 以 苯酚 为溶剂， 反应 7.0h， 以42%的产率得到6-amino-9-[11-(N-(4-(4-nitrobenzamido)butyl)acridin-9-yl-4-carboxamido)-3,7,11-triazaundecyl]-9H-purine trihydrochloride
  参考文献：
  名称：

  Design of site specific DNA damaging agents for generation of multiply damaged sites

  摘要：

  We describe the synthesis and DNA damaging activities of hybrid molecules in which a purine (adenine) is linked to an intercalating chromophore (acridine) by a polyamino linker. A DNA damaging agent, phenanthroline or para-nitrobenzamide, is tethered to the acridine moiety at various positions. Our goal is to induce upon activation other lesions in close proximity to the abasic site and therefore create cytotoxic multiply damaged sites. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00345-9
• 作为产物：
  描述：

  9-chloroacridine-4-carbonyl chloride 、 N-(4-aminobutyl)-4-nitrobenzamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到N-[4-(4-nitrobenzamido)butyl]-9-chloroacridine-4-carboxamide
  参考文献：
  名称：

  Design of site specific DNA damaging agents for generation of multiply damaged sites

  摘要：

  We describe the synthesis and DNA damaging activities of hybrid molecules in which a purine (adenine) is linked to an intercalating chromophore (acridine) by a polyamino linker. A DNA damaging agent, phenanthroline or para-nitrobenzamide, is tethered to the acridine moiety at various positions. Our goal is to induce upon activation other lesions in close proximity to the abasic site and therefore create cytotoxic multiply damaged sites. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00345-9

文献信息

• Photoreactive threading agent that specifically binds to abasic sites in DNA
  作者：Alain Martelli、Muriel Jourdan、Jean-François Constant、Martine Demeunynck、Pascal Dumy

  DOI：10.1016/j.bmcl.2005.09.026

  日期：2006.1

  We report the synthesis and study of a photoreactive nitrobenzamide containing acridine that specifically interacts at abasic site in DNA by threading intercalation and introduces under irradiation a lesion on the opposite strand at the unpaired pyrimidine. (c) 2005 Elsevier Ltd. All rights reserved.