Pentanediamide, 3-(9-acridinylamino)-N,N'-bis(6-(9-acridinylamino)hexyl)- | 98502-89-7

• 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: Pentanediamide, 3-(9-acridinylamino)-N,N'-bis(6-(9-acridinylamino)hexyl)-
• 英文别名: 3-(acridin-9-ylamino)-N,N'-bis[6-(acridin-9-ylamino)hexyl]pentanediamide
• CAS: 98502-89-7
• 化学式: C₅₆H₅₈N₈O₂
• 分子量: 875.129
• InChiKey: NPAOHTQCKSAIOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  66
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  133
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  {6-[3-Benzyloxycarbonylamino-4-(6-benzyloxycarbonylamino-hexylcarbamoyl)-butyrylamino]-hexyl}-carbamic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 115.0~120.0 ℃ 、413.69 kPa 条件下， 反应 15.0h， 生成 Pentanediamide, 3-(9-acridinylamino)-N,N'-bis(6-(9-acridinylamino)hexyl)-
  参考文献：
  名称：

  Potential antitumor agents. 45. Synthesis, DNA-binding interaction, and biological activity of triacridine derivatives

  摘要：

  A series of amide-linked triacridines of varying interchromophore separation were synthesized as potential DNA trisintercalating agents. The corresponding diamide diacridines (lacking the central chromophore) were also prepared, and the DNA-binding and biological activities of both series of compounds were evaluated. Although one of the triacridines shows evidence of a trisintercalative binding mode, most of the triacridines (and all the diacridines) bound by bisintercalation. The diacridines showed great cytotoxicity and higher DNA association constants than the corresponding 9-[[3-(dimethylamino)propyl]amino]acridine monomer, but addition of a third chromophore did not provide corresponding increases in either DNA affinity, inhibition of RNA synthesis, or cytotoxicity. Some members of both series show minimal in vivo antileukemic activity. The results suggest that further development of trimeric molecules as potential antitumor agents should focus on smaller chromophores with lower capacity for nonspecific binding and/or the employment of rigid linker chains to provide true molecular "staples" for DNA.

  DOI：

  10.1021/jm00151a011

文献信息

• Potential antitumor agents. 45. Synthesis, DNA-binding interaction, and biological activity of triacridine derivatives
  作者：Graham J. Atwell、Bruce C. Baguley、Dorota Wilmanska、William A. Denny

  DOI：10.1021/jm00151a011

  日期：1986.1

  A series of amide-linked triacridines of varying interchromophore separation were synthesized as potential DNA trisintercalating agents. The corresponding diamide diacridines (lacking the central chromophore) were also prepared, and the DNA-binding and biological activities of both series of compounds were evaluated. Although one of the triacridines shows evidence of a trisintercalative binding mode, most of the triacridines (and all the diacridines) bound by bisintercalation. The diacridines showed great cytotoxicity and higher DNA association constants than the corresponding 9-[[3-(dimethylamino)propyl]amino]acridine monomer, but addition of a third chromophore did not provide corresponding increases in either DNA affinity, inhibition of RNA synthesis, or cytotoxicity. Some members of both series show minimal in vivo antileukemic activity. The results suggest that further development of trimeric molecules as potential antitumor agents should focus on smaller chromophores with lower capacity for nonspecific binding and/or the employment of rigid linker chains to provide true molecular "staples" for DNA.