N,N <(amino-3 propyl) ethyl> N',N'<(amino-3 propyl) ethyl> butane diamine-1,4 | 113812-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N <(amino-3 propyl) ethyl> N',N'<(amino-3 propyl) ethyl> butane diamine-1,4
• 英文别名: N⁴,N⁹-diethylspermine；N,N [(amino-3 propyl) ethyl] N',N'[(amino-3 propyl) ethyl] butane diamine-1,4；1,4-Butanediamine, N,N'-bis(3-aminopropyl)-N,N'-diethyl-；N,N'-bis(3-aminopropyl)-N,N'-diethylbutane-1,4-diamine
• CAS: 113812-23-0
• 化学式: C₁₄H₃₄N₄
• 分子量: 258.451
• InChiKey: HCUFAPSHGYTZPM-UHFFFAOYSA-N

物化性质

• 沸点：
  351.1±10.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N <(amino-3 propyl) ethyl> N',N'<(amino-3 propyl) ethyl> butane diamine-1,4 以 乙醇 为溶剂， 反应 15.0h， 生成 6-{3-[Ethyl-(4-{ethyl-[3-(5-hydroxy-1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-propyl]-amino}-butyl)-amino]-propyl}-1,2-dihydro-6-aza-cyclopenta[cd]phenalene-5,7-dione
  参考文献：
  名称：

  Bis-naphthalimides. 2. Synthesis and biological activity of 5,6-acenaphthalimidoalkyl-1,8-naphthalimidoalkyl amines

  摘要：

  A series of non-symmetric bis-naphthalimides bearing a conveniently substituted 1,8-naphthalimide and a 5,6-acenaphthalimide chromophore was synthesized and in vitro activities were determined. Although previous studies suggested that the presence of the acenaphthalimide system in the structure enhances aqueous solubility, we found that these compounds were no more soluble or cytotoxic than the homologous symmetric series.

  DOI：

  10.1016/0223-5234(96)88230-4
• 作为产物：
  描述：

  精胺 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 216.0h， 生成 N,N <(amino-3 propyl) ethyl> N',N'<(amino-3 propyl) ethyl> butane diamine-1,4
  参考文献：
  名称：

  Garrigues, Bernard; Vidaud, Lionel, Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 10, p. 775 - 786

  摘要：

  DOI：

文献信息

• Synthetic polyamine analogs as antineoplastics
  作者：Raymond J. Bergeron、Allen H. Neims、James S. McManis、Thomas R. Hawthorne、John R. T. Vinson、Rita Bortell、Michael J. Ingeno

  DOI：10.1021/jm00401a019

  日期：1988.6

  In this paper, we report on the synthesis and biological activity of a number of N-alkylated spermine compounds. The dialkylspermines N1,N12-dimethylspermine (DMSPM-2), N1,N12-diethylspermine (DESPM-3), and N1,N12-dipropylspermine (DPSPM-4) are all shown to inhibit the growth of L1210 cells in culture with IC50 values of less than 1 microM at 96 h. Furthermore, DESPM-3 is shown to be similarly active against Daudi and HL-60 cells in culture. A structure-activity relationship is shown to exist between the position at which spermine is alkylated and its antiproliferative properties. The activity of 10 microM DESPM-3 against L1210 cells was shown to be cytostatic, with greater than 90% cell viability by trypan blue exclusion, even after a 144-h exposure. When L1210 cells were treated with 10 microM DESPM-3 over a 144-h period, their size and mitochondrial DNA content were gradually but substantially diminished. However, flow cytometric measurements of the nuclear DNA content of these treated cells at 96 h indicated only slightly reduced S and G2 populations and significant changes only after 144 h. A cloning assay performed on the cells after 96 h of exposure to this drug (10 microM) indicated that the cells were not growing. Finally, when male DBA/2 mice, inoculated with L1210 leukemia cells, were treated with DESPM-3, their life span was increased in excess of 200% relative to untreated controls. Moreover, many long-term survivors were apparently tumor free at the end of the experiment (60 days).
• BERGERON, RAYMOND J.;NEIMS, ALLEN H.;MCMANIS, JAMES S.;HAWTHORNE, THOMAS +, J. MED. CHEM., 31,(1988) N 6, 1183-1190
  作者：BERGERON, RAYMOND J.、NEIMS, ALLEN H.、MCMANIS, JAMES S.、HAWTHORNE, THOMAS +

  DOI：——

  日期：——
• BIS-NAPHTHALIMIDES AS ANTICANCER AGENTS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0532636A1

  公开（公告）日：1993-03-24
• US6583280B1
  申请人：——

  公开号：US6583280B1

  公开（公告）日：2003-06-24
• [EN] BIS-NAPHTHALIMIDES AS ANTICANCER AGENTS
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1991018884A1

  公开（公告）日：1991-12-12

  (EN) There are provided novel bis-naphthalimide compounds useful as antitumor agents, pharmaceutical compositions containing them and processes for preparing intermediates to such compounds.(FR) L'invention se rapporte à de nouveaux composés à base de bis-naphtalimides, qui sont utiles comme agents antitumoraux, à des compositions pharmaceutiques contenant ces composés et à des procédés servant à préparer des intermédiaires de ces composés.