4,5,6,7-tetrabromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2H-benzotriazole | 1621176-52-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5,6,7-tetrabromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2H-benzotriazole
• CAS: 1621176-52-0
• 化学式: C₁₂H₁₁Br₄N₃O₂
• 分子量: 548.854
• InChiKey: JQPYBOQMVJBDTO-UHFFFAOYSA-N

物化性质

• 沸点：
  537.2±60.0 °C(predicted)
• 密度：
  2.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.17
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,5,6,7-tetrabromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2H-benzotriazole 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以95 mg的产率得到3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propane-1,2-diol
  参考文献：
  名称：

  Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties

  摘要：

  The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral β-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2α catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 μM range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2α has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.019
• 作为产物：
  描述：

  T406石油添加剂 在 溴 、 硝酸 、 potassium carbonate 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 100.0h， 生成 4,5,6,7-tetrabromo-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2H-benzotriazole
  参考文献：
  名称：

  Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties

  摘要：

  The efficient method for the synthesis of novel 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) derivatives bearing a single stereogenic center has been developed. New compounds with a variety of substituents at the meta- and para-position of the phenyl ring are reported. All of the presented compounds were obtained using classical synthetic methods, such as bromination of benzotriazole, and its subsequent alkylation by monotosylated arylpropane-1,3-diols, which in turn have been synthesized through reduction of the corresponding prochiral β-keto esters, and the selective monotosylation of the primary hydroxyl group. The influence of the new and previously reported N-hydroxyalkyl TBBt derivatives on the activity of human protein kinase CK2α catalytic subunit was examined. The most active were derivatives with N-hydroxyalkyl substituents (IC50 in 0.80-7.35 μM range). A binding mode of (R)-1-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)butan-3-ol 7b to hCK2α has been proposed based on in silico docking studies. Additionally, MTT-based cytotoxicity tests demonstrated high activities of novel 1-aryl-3-TBBt-propan-1-ol and 3-TBBt-propan-1,2-diol derivatives against human peripheral blood T lymphoblast (CCRF-CEM), and moderate anti-tumor activities against human breast adenocarcinoma (MCF7) cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.019