2-(acridin-9-ylamino)-N-[3-(acridin-9-ylamino)propyl]acetamide | 97614-72-7

• 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: 2-(acridin-9-ylamino)-N-[3-(acridin-9-ylamino)propyl]acetamide
• CAS: 97614-72-7
• 化学式: C₃₁H₂₇N₅O
• 分子量: 485.588
• InChiKey: XDMRDCGRHWBUTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [3-(2-Benzyloxycarbonylamino-acetylamino)-propyl]-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 、 苯酚 作用下， 以 甲醇 为溶剂， 125.0 ℃ 、413.69 kPa 条件下， 反应 10.0h， 生成 2-(acridin-9-ylamino)-N-[3-(acridin-9-ylamino)propyl]acetamide
  参考文献：
  名称：

  Potential antitumor agents. 44. Synthesis and antitumor activity of new classes of diacridines: importance of linker chain rigidity for DNA binding kinetics and biological activity

  摘要：

  Four classes of diacridines, joined at the 9-position by linker chains of varying length, rigidity, and polarity, were evaluated for DNA-binding properties and antitumor activity. Diacridines linked by flexible chains of varying polarity show relatively fast chromophore exchange kinetics among DNA binding sites but slower dissociation rates, suggesting the potential for considerable "creeping" of the drug along the helix, and are inactive in vivo. The exchange kinetics can be slowed dramatically by inclusion of positive charges in the side chain, but the resulting polycationic drugs are inactive in vivo, possibly due to poor distribution. Diacridines linked by a rigid, polar but neutral dicarbamoylpyrazole chain retain slow exchange kinetics, have a greatly reduced potential "creep rate", and possess good in vitro potency and significant in vivo antileukemic activity.

  DOI：

  10.1021/jm00149a005

文献信息

• Potential antitumor agents. 44. Synthesis and antitumor activity of new classes of diacridines: importance of linker chain rigidity for DNA binding kinetics and biological activity
  作者：William A. Denny、Graham J. Atwell、Bruce C. Baguley、Laurence P. G. Wakelin

  DOI：10.1021/jm00149a005

  日期：1985.11

  Four classes of diacridines, joined at the 9-position by linker chains of varying length, rigidity, and polarity, were evaluated for DNA-binding properties and antitumor activity. Diacridines linked by flexible chains of varying polarity show relatively fast chromophore exchange kinetics among DNA binding sites but slower dissociation rates, suggesting the potential for considerable "creeping" of the drug along the helix, and are inactive in vivo. The exchange kinetics can be slowed dramatically by inclusion of positive charges in the side chain, but the resulting polycationic drugs are inactive in vivo, possibly due to poor distribution. Diacridines linked by a rigid, polar but neutral dicarbamoylpyrazole chain retain slow exchange kinetics, have a greatly reduced potential "creep rate", and possess good in vitro potency and significant in vivo antileukemic activity.