N,N'-bis<3-(diethylamino)propyl>succinamide | 63958-61-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-bis<3-(diethylamino)propyl>succinamide
• 英文别名: bis(N,N-diethylaminopropyl)succinamide；N~1~,N~4~-Bis[3-(diethylamino)propyl]butanediamide；N,N'-bis[3-(diethylamino)propyl]butanediamide
• CAS: 63958-61-2
• 化学式: C₁₈H₃₈N₄O₂
• 分子量: 342.525
• InChiKey: HZUWKOWOPFJJLI-UHFFFAOYSA-N

物化性质

• 沸点：
  545.8±45.0 °C(Predicted)
• 密度：
  0.972±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis<3-(diethylamino)propyl>succinamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以0.64 g的产率得到N¹,N¹,N¹²,N¹²-tetraethylspermine
  参考文献：
  名称：

  Synthetic polyamine analogs as antineoplastics

  摘要：

  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).

  DOI：

  10.1021/jm00401a019
• 作为产物：
  描述：

  3-二乙胺基丙胺 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 N,N'-bis<3-(diethylamino)propyl>succinamide
  参考文献：
  名称：

  De; Seth; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 3, p. 231 - 234

  摘要：

  DOI：

文献信息

• DE, DIBYENDU;SETH, M.;BHADURI, A. P., INDIAN J. CHEM. B, 29,(1990) N, C. 231-234
  作者：DE, DIBYENDU、SETH, M.、BHADURI, A. P.

  DOI：——

  日期：——
• 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：——
• De; Seth; Bhaduri, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 3, p. 231 - 234
  作者：De、Seth、Bhaduri

  DOI：——

  日期：——
• 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).