{2-(3-Amino-propylcarbamoyl)-1-[(3-amino-propylcarbamoyl)-methyl]-ethyl}-carbamic acid tert-butyl ester | 98577-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {2-(3-Amino-propylcarbamoyl)-1-[(3-amino-propylcarbamoyl)-methyl]-ethyl}-carbamic acid tert-butyl ester
• CAS: 98577-87-8
• 化学式: C₁₆H₃₃N₅O₄
• 分子量: 359.469
• InChiKey: ODQMOZUESAASRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  148.57
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {2-(3-Amino-propylcarbamoyl)-1-[(3-amino-propylcarbamoyl)-methyl]-ethyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 N,N-二甲基乙酰胺 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N,N'-bis[3-(acridin-9-ylamino)propyl]-3-aminopentanediamide;hydrochloride
  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
• 作为产物：
  描述：

  3-aminoglutaric acid hydrochloride 在 palladium on activated charcoal 氢氧化钾 、 氰基磷酸二乙酯 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、413.69 kPa 条件下， 反应 25.5h， 生成 {2-(3-Amino-propylcarbamoyl)-1-[(3-amino-propylcarbamoyl)-methyl]-ethyl}-carbamic acid tert-butyl ester
  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