1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol | 1621176-43-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol
• 英文别名: 1-(4-Chlorophenyl)-3-(4,5,6,7-tetrabromobenzotriazol-2-yl)propan-1-ol；1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromobenzotriazol-2-yl)propan-1-ol
• CAS: 1621176-43-9
• 化学式: C₁₅H₁₀Br₄ClN₃O
• 分子量: 603.333
• InChiKey: ZYWCBXXXTQSNHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苯甲酰乙酸甲酯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 77.25h， 生成 1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol
  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

文献信息

• Synthesis of novel chiral TBBt derivatives with hydroxyl moiety. Studies on inhibition of human protein kinase CK2α and cytotoxicity properties
  作者：Paweł Borowiecki、Adam M. Wawro、Patrycja Wińska、Monika Wielechowska、Maria Bretner

  DOI：10.1016/j.ejmech.2014.07.019

  日期：2014.9

  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.