4,4’-dihydroxy-3,3’-di-(trimethylammonium iodide-methyl)biphenyl

• 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: 4,4’-dihydroxy-3,3’-di-(trimethylammonium iodide-methyl)biphenyl
• 英文别名: 4,4'-dihydroxy-3,3'-di-(trimethylammonium iodide-methyl) biphenyl；[2-Hydroxy-5-[4-hydroxy-3-[(trimethylazaniumyl)methyl]phenyl]phenyl]methyl-trimethylazanium;iodide
• 化学式: C₂₀H₃₀N₂O₂*2I
• 分子量: 584.279
• InChiKey: UPSORWVEIGNHJY-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 4,4’-dihydroxy-3,3’-di-(trimethylammonium iodide-methyl)biphenyl 生成 3,3'-Bis-(tert-butylamino-methyl)-biphenyl-4,4'-diol
  参考文献：
  名称：

  Biological studies of photoinducible phenol quaternary ammonium derivatives

  摘要：

  Three water-soluble DNA cross-linking phenol quaternary ammonium derivatives 3, 4, and 5 could inhibit the transcription in vitro by photoactivation. DNA interstrand cross-linking action might be the key factor to inhibit transcription by these compounds. Further tumor cell apoptosis was observed by flow cytometry it indicated that cross-linking agent 5 could significantly induce the late apoptosis of tumor cells. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.007
• 作为产物：
  描述：

  4,4'-二羟基联苯 以 乙醇 、 乙腈 为溶剂， 反应 6.0h， 生成 4,4’-dihydroxy-3,3’-di-(trimethylammonium iodide-methyl)biphenyl
  参考文献：
  名称：

  A Potent, Water-Soluble and Photoinducible DNA Cross-Linking Agent

  摘要：

  Water-soluble DNA cross-linking phenol and biphenol derivatives 3 and 6 have been synthesized by a Mannich reaction. Both of them can cross-link DNA by photoactivation using visible light (wavelength > 400 nm). Compound 6 can cross-link DNA at pH 5.0 and 7.7, whereas no cross-link was observed at pH 10.0. Density functional theory (DFT) calculation indicated that 6 displays a twist structure. Therefore, it could bind to DNA naturally and has potent property to cross-link DNA after photoactivation.

  DOI：

  10.1021/ja029040o

文献信息

• A thiol-inducible and quick-response DNA cross-linking agent
  作者：Yuanzhen Xu、Hongbo Wei、Jianjun Chen、Kun Gao

  DOI：10.1016/j.bmcl.2018.11.040

  日期：2019.1

  release the corresponding phenol derivatives (4–6) within 5 min. The quick response of 1–3 toward thiols was determined by 1H NMR and HPLC. Moreover, our results indicated that 1 could induce DNA cross-linking in the presence of glutathione, probably due to the quinone methide formation of phenol intermediate 4 followed by departure of 2,4-dinitrobenzenesulfonyl group.

  三个新的2,4-二硝基苯衍生物1 - 3使用一个简单的过程中的第一次成功制备。它们被硫醇（谷胱甘肽和1-半胱氨酸）有效触发，在5分钟内释放出相应的苯酚衍生物（4 – 6）。的快速反应1 - 3朝向硫醇通过测定1 H NMR和HPLC。此外，我们的结果表明1可以在存在谷胱甘肽的情况下诱导DNA交联，这可能是由于苯酚中间体4的醌甲基化物形成，接着是2,4-二硝基苯磺酰基的离开。