N1,N1-dimethyl-N2-(4,5,6,7-tetraiodo-1H-benzimidazol-2-yl)-ethane-1,2-diamine | 1391137-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N1,N1-dimethyl-N2-(4,5,6,7-tetraiodo-1H-benzimidazol-2-yl)-ethane-1,2-diamine
• 英文别名: N',N'-dimethyl-N-(4,5,6,7-tetraiodo-1H-benzimidazol-2-yl)ethane-1,2-diamine
• CAS: 1391137-10-2
• 化学式: C₁₁H₁₂I₄N₄
• 分子量: 707.861
• InChiKey: DNLDQPLIENTICN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-bromo-,4,5,6,7-tetraiodo-1H-benzimidazole 、 N,N-二甲基乙二胺 以 乙二醇甲醚 为溶剂， 反应 10.0h， 以47%的产率得到N1,N1-dimethyl-N2-(4,5,6,7-tetraiodo-1H-benzimidazol-2-yl)-ethane-1,2-diamine
  参考文献：
  名称：

  Modified tetrahalogenated benzimidazoles with CK2 inhibitory activity are active against human prostate cancer cells LNCaP in vitro

  摘要：

  A series of novel CK2 inhibitors, tetrahalogenated benzimidazoles carrying an aminoalkylamino group at position 2, has been prepared by nucleophilic substitution of the respective 2,4,5,6,7-pentabromobenzimidazoles and 2-bromo-4,5,6,7-tetraiodobenzimidazoles. The new derivatives as well as some previously obtained tetrahalogenobenzimidazoles, including 4,5,6,7-tetrabromobenzimidazole (TBI) and 4,5,6,7-tetraiodobenzimidazole (TIBI), were evaluated for activity against the hormone-sensitive human prostate cancer cell line LNCaP. The activity of 2-aminoalkylamino derivatives was notably higher (LD50 4.75-9.37 mu M) than that of TBI and TIBI (LD50 approximate to 20 mu M). The determination of the LD50 value identified the 2-aminoethylamino-4,5,6,7-tetraiodobenzimidazole with an additional methyl group at position 1 (6) as the most efficient compound (LD50: 4.75 +/- 1.02 mu M). Interestingly, there was no clear correlation between cell viability and apoptosis induction indicating additional cell death mechanisms. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.038

文献信息

• Modified tetrahalogenated benzimidazoles with CK2 inhibitory activity are active against human prostate cancer cells LNCaP in vitro
  作者：Carolin C. Schneider、Sabine Kartarius、Mathias Montenarh、Andrzej Orzeszko、Zygmunt Kazimierczuk

  DOI：10.1016/j.bmc.2012.05.038

  日期：2012.7

  A series of novel CK2 inhibitors, tetrahalogenated benzimidazoles carrying an aminoalkylamino group at position 2, has been prepared by nucleophilic substitution of the respective 2,4,5,6,7-pentabromobenzimidazoles and 2-bromo-4,5,6,7-tetraiodobenzimidazoles. The new derivatives as well as some previously obtained tetrahalogenobenzimidazoles, including 4,5,6,7-tetrabromobenzimidazole (TBI) and 4,5,6,7-tetraiodobenzimidazole (TIBI), were evaluated for activity against the hormone-sensitive human prostate cancer cell line LNCaP. The activity of 2-aminoalkylamino derivatives was notably higher (LD50 4.75-9.37 mu M) than that of TBI and TIBI (LD50 approximate to 20 mu M). The determination of the LD50 value identified the 2-aminoethylamino-4,5,6,7-tetraiodobenzimidazole with an additional methyl group at position 1 (6) as the most efficient compound (LD50: 4.75 +/- 1.02 mu M). Interestingly, there was no clear correlation between cell viability and apoptosis induction indicating additional cell death mechanisms. (C) 2012 Elsevier Ltd. All rights reserved.