(4,5,6,7-tetrabromo-1H-benzimidazol-1-yl)-acetic acid | 1196457-26-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4,5,6,7-tetrabromo-1H-benzimidazol-1-yl)-acetic acid
• 英文别名: K68；(4,5,6,7-Tetrabromo-1h-Benzimidazol-1-Yl)acetic Acid；2-(4,5,6,7-tetrabromobenzimidazol-1-yl)acetic acid
• CAS: 1196457-26-7
• 化学式: C₉H₄Br₄N₂O₂
• 分子量: 491.759
• InChiKey: WIMPWBKZHKEQQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5,6,7-四溴-1H-苯并咪唑 在 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (4,5,6,7-tetrabromo-1H-benzimidazol-1-yl)-acetic acid
  参考文献：
  名称：

  CK2α and CK2α′ subunits differ in their sensitivity to 4,5,6,7-tetrabromo- and 4,5,6,7-tetraiodo-1H-benzimidazole derivatives

  摘要：

  The goal of this study was to test the inhibitory activity of a series of tetrahalogenobenzimidazoles, including a number of novel derivatives, on individual catalytic subunits of human CK2. 4,5,6,7-tetrabromo- and 4,5,6,7-tetraiodo-1H-benzimidazoles and their newly obtained N-1- and 2-S-carboxyalkyl derivatives showed potent inhibitory activity against both these subunits. CK2 alpha' was up to 6 times more sensitive to the studied compounds than CK2 alpha. The investigated iododerivatives showed, in most cases, stronger inhibitory properties than the respective brominated congeners, but the differences showed considerable dependence on the protein substrate used. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.002

文献信息

• Tetraiodobenzimidazoles are potent inhibitors of protein kinase CK2
  作者：Alessandra Gianoncelli、Giorgio Cozza、Andrzej Orzeszko、Flavio Meggio、Zygmunt Kazimierczuk、Lorenzo A. Pinna

  DOI：10.1016/j.bmc.2009.08.047

  日期：2009.10

  have been prepared by iodination of respective benzimidazole with iodine and periodic acid in sulfuric acid solution. Additionally several 2-substituted- and N-1-carboxymethyl-substituted derivatives of 4,5,6,7-tetraiodobenzimidazole (TIBI) were obtained. For sake of comparison, some new 4,5,6,7-tetrabromobenzimidazoles were also synthesized. The ability of the new compounds to inhibit protein kinase

  通过将各自的苯并咪唑与碘和高碘酸在硫酸溶液中碘化，已经制备了一系列新的碘代苯并咪唑。另外几个2个取代基和N获得了4,5,6,7-四碘代苯并咪唑（TIBI）的-1-羧甲基取代的衍生物。为了比较，还合成了一些新的4,5,6,7-四溴苯并咪唑。已经评估了新化合物抑制蛋白激酶CK2的能力。结果表明，4,5,6,7-四碘代苯并咪唑类比四溴代类似物更有效地抑制CK2。分子建模支持的实验数据表明，四碘代苯并咪唑部分比各自的四溴和四氯化合物填充的结合腔更好。要注意的是，4,5,6,7-四碘代苯并咪唑（TIBI）是 迄今为止描述的最有效的CK2抑制剂（K i = 23 nM）之一。
• BISUBSTRATE FLUORESCENT PROBES FOR PROTEIN KINASE CK2
  申请人：University of Tartu

  公开号：US20140057291A1

  公开（公告）日：2014-02-27

  This invention relates to fluorescent probes for screening and characterization of compounds binding to protein kinase CK2, measurement of concentration of the catalytically active form of CK2 and imaging of CK2 activity in cells and tissues. The CK2-selective probe of the present invention interacts with binding sites of both substrates of the catalytic subunit of CK2 and therefore can be used for characterization of all inhibitors binding to the active site of CK2 in the binding/displacement assay. The high affinity of the probe affords the detection of the enzyme at low concentration and characterization of inhibitors in a wide affinity range. The invention also relates to the application of the probes for mapping and monitoring of CK2 activity in cells, tissues and live organisms.

  本发明涉及用于筛选和表征结合到蛋白激酶CK2的化合物、测量CK2催化活性形式的浓度以及在细胞和组织中成像CK2活性的荧光探针。本发明的CK2选择性探针与CK2催化亚基的两个底物的结合位点相互作用，因此可用于特征化所有结合到CK2活性位点的抑制剂在结合/置换试验中的作用。探针的高亲和力可在低浓度下检测酶并特征化广泛亲和力范围内的抑制剂。本发明还涉及将探针应用于细胞、组织和活体中CK2活性的映射和监测。
• US9176064B2
  申请人：——

  公开号：US9176064B2

  公开（公告）日：2015-11-03
• CK2α and CK2α′ subunits differ in their sensitivity to 4,5,6,7-tetrabromo- and 4,5,6,7-tetraiodo-1H-benzimidazole derivatives
  作者：Monika Janeczko、Andrzej Orzeszko、Zygmunt Kazimierczuk、Ryszard Szyszka、Andrea Baier

  DOI：10.1016/j.ejmech.2011.11.002

  日期：2012.1

  The goal of this study was to test the inhibitory activity of a series of tetrahalogenobenzimidazoles, including a number of novel derivatives, on individual catalytic subunits of human CK2. 4,5,6,7-tetrabromo- and 4,5,6,7-tetraiodo-1H-benzimidazoles and their newly obtained N-1- and 2-S-carboxyalkyl derivatives showed potent inhibitory activity against both these subunits. CK2 alpha' was up to 6 times more sensitive to the studied compounds than CK2 alpha. The investigated iododerivatives showed, in most cases, stronger inhibitory properties than the respective brominated congeners, but the differences showed considerable dependence on the protein substrate used. (C) 2011 Elsevier Masson SAS. All rights reserved.