3,7,11,16,20,24-hexakis(p-tolylsulfonyl)-3,7,11,16,20,24-hexaazahexacosane | 113812-29-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,7,11,16,20,24-hexakis(p-tolylsulfonyl)-3,7,11,16,20,24-hexaazahexacosane
• 英文别名: 3,7,11,16,20,24-Hexa(p-toluenesulfonyl)3,7,11,16,20,24-hexaazahexacosane；N-ethyl-N-[3-[3-[4-[3-[3-[ethyl-(4-methylphenyl)sulfonylamino]propyl-(4-methylphenyl)sulfonylamino]propyl-(4-methylphenyl)sulfonylamino]butyl-(4-methylphenyl)sulfonylamino]propyl-(4-methylphenyl)sulfonylamino]propyl]-4-methylbenzenesulfonamide
• CAS: 113812-29-6
• 化学式: C₆₂H₈₄N₆O₁₂S₆
• 分子量: 1297.78
• InChiKey: IJUWVYNKSVDVSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  86
• 可旋转键数：
  35
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  275
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  3,7,11,16,20,24-hexakis(p-tolylsulfonyl)-3,7,11,16,20,24-hexaazahexacosane 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以0.216 g的产率得到1,20-bis(N-ethylamino)-4,8,13,17-tetraazaeicosane
  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：

  N-乙基对甲苯磺酰胺 在 sodium hydride 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 3,7,11,16,20,24-hexakis(p-tolylsulfonyl)-3,7,11,16,20,24-hexaazahexacosane
  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

文献信息

• Anti-neoplastic, anti-viral or anti-retroviral spermine derivatives
  申请人：——

  公开号：US20020094990A1

  公开（公告）日：2002-07-18

  The present invention relates to anti-neoplastic and anti-psoriasis pharmaceutical compositions and methods of treatment and to insecticidal compositions and methods of controlling the growth of insects.

  本发明涉及抗肿瘤和抗牛皮癣药物组合物和治疗方法，以及杀虫组合物和控制昆虫生长的方法。
• 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：——
• US5091576A
  申请人：——

  公开号：US5091576A

  公开（公告）日：1992-02-25
• US5342945A
  申请人：——

  公开号：US5342945A

  公开（公告）日：1994-08-30
• US5455277A
  申请人：——

  公开号：US5455277A

  公开（公告）日：1995-10-03