5,5'-dihydroxy-(2,2'-diselenobisbenzoic acid) | 1239668-62-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-dihydroxy-(2,2'-diselenobisbenzoic acid)
• CAS: 1239668-62-2
• 化学式: C₁₄H₁₀O₆Se₂
• 分子量: 432.15
• InChiKey: ZFOJVKDIHAJMEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  115.06
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5,5'-dihydroxy-(2,2'-diselenobisbenzoic acid) 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-(8-((tert-butoxycarbonyl)oxy)-7-chloroquinolin-5-yl)-3-oxo-2,3-dihydrobenzo[d][1,2]selenazol-5-yl acetate
  参考文献：
  名称：

  Computer-assisted designed “selenoxy–chinolin”: a new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation

  摘要：

  利用理性计算机辅助设计的支持，通过融合金属螯合剂CQ和抗氧化剂ebselen设计的新型混合物系列被合成并评估为多靶点定向配体。

  DOI：

  10.1039/c5dt02130h
• 作为产物：
  描述：

  2-氨基-5-羟基苯甲酸 在 sodium nitrite 、 disodium diselenide 作用下， 生成 5,5'-dihydroxy-(2,2'-diselenobisbenzoic acid)
  参考文献：
  名称：

  Computer-assisted designed “selenoxy–chinolin”: a new catalytic mechanism of the GPx-like cycle and inhibition of metal-free and metal-associated Aβ aggregation

  摘要：

  利用理性计算机辅助设计的支持，通过融合金属螯合剂CQ和抗氧化剂ebselen设计的新型混合物系列被合成并评估为多靶点定向配体。

  DOI：

  10.1039/c5dt02130h

文献信息

• Selenium containing macrocycles: transformation between Se–N/Se–S/Se–Se bonds
  作者：Shaobo Ji、Hicham El Mard、Mario Smet、Wim Dehaen、Huaping Xu

  DOI：10.1007/s11426-017-9059-4

  日期：2017.9

  dithiothreitol, forming Se–S linked dimer (D1). To realize the transformation from Se–S bonds to Se–Se bonds, guest molecules were added as template, triggering the formation of Se–Se linked dimer (D2). The formation of these two new kinds of macrocycles was determined by 1H NMR and 77Se NMR, and the necessity of guest molecules was also confirmed. The introduction of ebselen moieties and Se–S bonds or Se–Se

  大环化合物在超分子化学和生物系统中具有潜在的应用。因此，开发新型的大环具有重要意义。在这里，通过硒相关的动态共价键之间的转化合成了含有Se-Se / Se-S键的新型大环。合成了包含两个ebselen部分的单体（M1）。二硫苏糖醇还原M1中的Se–N键，形成Se–S连接的二聚体（D1）。为了实现从Se–S键到Se–Se键的转变，添加了客体分子作为模板，触发了Se–Se连接的二聚体（D2）的形成。这两种新的大环的形成是通过1 H NMR和77还确认了Se NMR和客体分子的必要性。将ebselen部分和Se-S键或Se-Se键引入大环可能为其赋予了新的响应性和生物活性，以及​​新型的宿主-客体化学。
• Inhibition of thioredoxin reductase by a novel series of bis-1,2-benzisoselenazol-3(2H)-ones: Organoselenium compounds for cancer therapy
  作者：Jie He、Dongdong Li、Kun Xiong、Yongjie Ge、Hongwei Jin、Guozhou Zhang、Mengshi Hong、Yongliang Tian、Jin Yin、Huihui Zeng

  DOI：10.1016/j.bmc.2012.04.033

  日期：2012.6

  Thioredoxin reductase (TrxR) is critical for cellular redox regulation and is involved in tumor proliferation, apoptosis and metastasis. Its C-terminal redox-active center contains a cysteine (Cys497) and a unique selenocysteine (Sec498), which are exposed to solvent and easily accessible. Thus, it is becoming an important target for anticancer drugs. Selective inhibition of TrxR by 1,2-(bis-1,2-benzisoselenazol-3(2H)-one)ethane (4a) prevents proliferation of several cancer cell lines both in vivo and in vitro. Using the structure of 4a as a starting point, a series of novel bis-1,2-benzisoselenazol-3(2H)-ones was designed, prepared and tested to explore the structure-activity relationships (SARs) for this class of inhibitor and to improve their potency. Notably, 1,2-(5,5'-dimethoxybis(1,2-benzisoselenazol-3(2H)-one))ethane (12) was found to be more potent than 4a in both in vitro and in vivo evaluation. Its binding sites were confirmed by biotin-conjugated iodoacetamide assay and a SAR model was generated to guide further structural modification. (C) 2012 Elsevier Ltd. All rights reserved.