1,3-di(4-carboxyphenyl)isobenzofuran | 1213236-94-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: 1,3-di(4-carboxyphenyl)isobenzofuran
• 英文别名: 4-[3-(4-Carboxyphenyl)-2-benzofuran-1-yl]benzoic acid；4-[3-(4-carboxyphenyl)-2-benzofuran-1-yl]benzoic acid
• CAS: 1213236-94-2
• 化学式: C₂₂H₁₄O₅
• 分子量: 358.35
• InChiKey: SMSCXWZXXFNXBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-di(4-carboxyphenyl)isobenzofuran 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以87%的产率得到
  参考文献：
  名称：

  水溶性 1,3-二芳基异苯并杂：合成和表征

  摘要：

  开发了水溶性 1,3-二芳基异苯并杂酚（包括异苯并呋喃、异苯并噻吩和异苯并硒酚）的有效合成路线。基于我们的二芳基异苯并呋喃的一锅合成方法，新的 D-π-D 和 A-π-A 类型的二芳基异苯并杂环变得容易获得，并且它们可以顺利地转化为水溶性异苯并杂环。还评估了新制备的异苯并杂环的光物理性质。

  DOI：

  10.1246/cl.170137
• 作为产物：
  描述：

  2-醛基苯甲酸甲酯 在 正丁基锂 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 22.17h， 生成 1,3-di(4-carboxyphenyl)isobenzofuran
  参考文献：
  名称：

  水溶性 1,3-二芳基异苯并杂：合成和表征

  摘要：

  开发了水溶性 1,3-二芳基异苯并杂酚（包括异苯并呋喃、异苯并噻吩和异苯并硒酚）的有效合成路线。基于我们的二芳基异苯并呋喃的一锅合成方法，新的 D-π-D 和 A-π-A 类型的二芳基异苯并杂环变得容易获得，并且它们可以顺利地转化为水溶性异苯并杂环。还评估了新制备的异苯并杂环的光物理性质。

  DOI：

  10.1246/cl.170137

文献信息

• A Nucleic Acid Dependent Chemical Photocatalysis in Live Human Cells
  作者：Dumitru Arian、Emiliano Cló、Kurt V. Gothelf、Andriy Mokhir

  DOI：10.1002/chem.200902377

  日期：2010.1.4

  Only two nucleic acid directed chemical reactions that are compatible with live cells have been reported to date. Neither of these processes generate toxic species from nontoxic starting materials. Reactions of the latter type could be applied as gene‐specific drugs, for example, in the treatment of cancer. We report here the first example of a chemical reaction that generates a cytotoxic drug from

  迄今为止，仅报道了两种与活细胞相容的核酸定向化学反应。这些过程均未从无毒的原料中产生有毒物质。后一种类型的反应可以用作基因特异性药物，例如，用于治疗癌症。我们在这里报告化学反应的第一个例子，该化学反应在活的哺乳动物细胞中存在特定内源性核糖核酸的情况下，从无毒前药产生细胞毒性药物。在这种情况下，前药是三线态氧而药物是单线态氧。该反应的关键成分是惰性分子（InP-2'-OMe-RNA / Q-2'-OMe-RNA; P：光敏剂; Q：淬灭剂），其成为活性光敏剂（InP-2'-OMe ‐RNA）存在单链核酸靶标的情况。在红光照射下，光敏剂每个核酸靶标产生6000多当量的有毒单重态氧。该反应是高度序列特异性的。为了检测活细胞中单线态氧的产生，我们制备了一种可透过膜和水溶性的荧光清除剂，它是2,5-二苯基异苯并呋喃的衍生物。与单线态氧反应后，清除剂分解，这表现为荧光强度降低。可通过流式细胞术方便地监
• Control of the Photocatalytic Activity of Bimetallic Complexes of Pyropheophorbide-<i>a</i> by Nucleic Acids
  作者：Dumitru Arian、Larisa Kovbasyuk、Andriy Mokhir

  DOI：10.1021/ic201408h

  日期：2011.12.5

  Photo catalytic activity of a photosensitizer (PS) in an oligodeoxyribonucleotide duplex 5'-PS similar to ODN1/ODN2 similar to Q-3' is inhibited because of close proximity of a quencher Q, The ODN2 in this duplex is selected to be longer than the ODN1. Therefore, in the presence of a nucleic acid (analyte), which is fully complementary to the ODN2 strand, the duplex is decomposed with formation of an analyte/ODN2Q duplex and a catalytically active, single stranded PS similar to ODN1. In this way the catalytic activity of the PS can be controlled by the specific nucleic acids. We applied this reaction earlier for the amplified detection of ribonucleic acids in live cells (Arian, D.; Clo, E.; Gothelf, K; Mokhir, A. Chem.- Ear J. 2010, 16(1), 288). As a photosensitizer (PS) we used In3+(pyropheophorbide-a)chloride and as a quencher (Q) - Black-Hole-Quencher-3 (BHQ-3). The In3+ complex is a highly active photocatalyst in aqueous solution. However, it can coordinate additional ligands containing thiols (e.g., proteins, peptides, and aminoacids), that modulate properties of the complex itself and of the corresponding bio- molecules. These possible interactions can lead to undesired side effects of nucleic acid controlled photocatalysts (PS similar to ODN1/ODN2-Q) in live cells. In this work we explored the possibility to substitute the In3+ complex for those ones of divalent metal ions, Zn2+ and Pd2+, which exhibit lower or no tendency to coordinate the fifth ligand. We found that one of the compounds tested (Pd(pyropheophorbide-a) is as potent and as stable photosensitizer as its In3+ analogue, but does not coordinate additional ligands that makes it more suitable for cellular applications. When the Pd complex was introduced in the duplex PS similar to ODN1/ODN2-Qas a PS, its photocatalytic activity could be controlled by nucleic acids as efficiently as that of the corresponding In3+ complex.