2-bromo-4,5,6,7-tetraiodo-1-methyl-1H-benzimidazole | 1391137-03-3

• 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: 2-bromo-4,5,6,7-tetraiodo-1-methyl-1H-benzimidazole
• CAS: 1391137-03-3
• 化学式: C₈H₃BrI₄N₂
• 分子量: 714.647
• InChiKey: KDBSCWALAXKAKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.82
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-bromo-4,5,6,7-tetraiodo-1-methyl-1H-benzimidazole 、 乙二胺 以 二甲基亚砜 为溶剂， 反应 0.75h， 以91%的产率得到N1-(4,5,6,7-tetraiodo-1-methyl-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
• 作为产物：
  描述：

  2-bromo-,4,5,6,7-tetraiodo-1H-benzimidazole 、 碘甲烷 在 sodium ethanolate 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 1.0h， 以72%的产率得到2-bromo-4,5,6,7-tetraiodo-1-methyl-1H-benzimidazole
  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