(E)-4-((4-hydroxyphenyl)diazenyl)benzoic acid methyl ester | 151901-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: (E)-4-((4-hydroxyphenyl)diazenyl)benzoic acid methyl ester
• 英文别名: 4-[2-(4-hydroxyphenyl)diazenyl]benzoic acid-methyl ester；methyl (E)-4-((4-hydroxyphenyl)diazenyl)benzoate
• CAS: 151901-38-1
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: DRPBGLUKSFZDGU-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.25
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-4-((4-hydroxyphenyl)diazenyl)benzoic acid methyl ester 在 18-冠醚-6 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 DPTS 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 168.0h， 生成
  参考文献：
  名称：

  Long-Range Ordering of Highly Charged Self-Assembled Nanofilaments

  摘要：

  Charged nanoscale filaments are well-known in natural systems such as filamentous viruses and the cellular cytoskeleton. The unique properties of these structures have inspired the design of self-assembled nanofibers for applications in regenerative medicine, drug delivery, and catalysis, among others. We report here on an amphiphile of completely different chemistry based on azobenzene and a quaternary ammonium bromide headgroup that self-assembles into highly charged nanofibers in water and orders into two-dimensional crystals. Interestingly small-angle X-ray scattering (SAXS) shows that these fibers of 5.6 nm cross-sectional diameter order into crystalline arrays with remarkably large interfiber spacings of up to 130 nm. Solution concentration and temperature can be adjusted to control the interfiber spacings, and addition of salt destroyed the crystal packing indicating the electrostatic repulsions are necessary for the observed ordering. Our findings here demonstrate the universal nature of this phenomenon in systems of highly charged nanoscale filaments.

  DOI：

  10.1021/ja5082519
• 作为产物：
  描述：

  对氨基苯甲酸 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 73.5h， 生成 (E)-4-((4-hydroxyphenyl)diazenyl)benzoic acid methyl ester
  参考文献：
  名称：

  Long-Range Ordering of Highly Charged Self-Assembled Nanofilaments

  摘要：

  Charged nanoscale filaments are well-known in natural systems such as filamentous viruses and the cellular cytoskeleton. The unique properties of these structures have inspired the design of self-assembled nanofibers for applications in regenerative medicine, drug delivery, and catalysis, among others. We report here on an amphiphile of completely different chemistry based on azobenzene and a quaternary ammonium bromide headgroup that self-assembles into highly charged nanofibers in water and orders into two-dimensional crystals. Interestingly small-angle X-ray scattering (SAXS) shows that these fibers of 5.6 nm cross-sectional diameter order into crystalline arrays with remarkably large interfiber spacings of up to 130 nm. Solution concentration and temperature can be adjusted to control the interfiber spacings, and addition of salt destroyed the crystal packing indicating the electrostatic repulsions are necessary for the observed ordering. Our findings here demonstrate the universal nature of this phenomenon in systems of highly charged nanoscale filaments.

  DOI：

  10.1021/ja5082519

文献信息

• INHIBIT logic operations based on light-driven β-cyclodextrin pseudo[1]rotaxane with room temperature phosphorescence addresses
  作者：Jingjing Cao、Xiang Ma、Mingri Min、Tiantian Cao、Shuaifan Wu、He Tian

  DOI：10.1039/c3cc49820d

  日期：——

  INHIBIT logic gates based on light-driven β-cyclodextrin pseudo[1]rotaxane were fabricated conveniently utilizing reversible ICD and RTP as output addresses respectively.

  基于光驱动β-环糊精伪[1]轮烷的INHIBIT逻辑门被方便地制造出来，分别利用可逆的ICD和RTP作为输出地址。
• Azo-PROTAC: Novel Light-Controlled Small-Molecule Tool for Protein Knockdown
  作者：Yu-Hui Jin、Meng-Chen Lu、Yan Wang、Wen-Xin Shan、Xuan-Yu Wang、Qi-Dong You、Zheng-Yu Jiang

  DOI：10.1021/acs.jmedchem.9b02058

  日期：2020.5.14

  designed photoswitchable azobenzene-proteolysis targeting chimeras (Azo-PROTACs) by including azobenzene moieties between ligands for the E3 ligase and the protein of interest. Azo-PROTACs are light-controlled small-molecule tools for protein knockdown in cells. The light-induced configuration change can switch the active state to induce protein degradation activity, which can be reversely controlled

  可逆地改变内源性蛋白质水平是持续存在的问题。在这里，我们设计了针对嵌合体（Azo-PROTACs）的光开关偶氮苯蛋白水解靶向嵌合体（Azo-PROTACs），方法是在E3连接酶的配体和目标蛋白之间包括偶氮苯部分。偶氮PROTAC是光控小分子工具，用于细胞中的蛋白敲低。光诱导的构型变化可以切换活性状态以诱导蛋白质降解活性，而蛋白质降解活性可以通过完整细胞中的曝光来反向控制。我们比较了具有不同构型和接头长度的偶氮PROTAC的蛋白质降解能力。在骨髓性白血病K562细胞中使用对BCR-ABL融合蛋白和ABL蛋白具有最佳降解能力的稳定形式，
• 一种蛋白靶向降解嵌合分子、制备方法及应用
  申请人：中国药科大学

  公开号：CN109761970B

  公开（公告）日：2020-06-09

  本发明公开了一种蛋白靶向降解嵌合分子、制备方法及应用。本发明提供的蛋白靶向降解嵌合分子可不同程度地抑制BCR‑ABL和/或CRBN阳性的白血病K562细胞中BCR‑ABL和/或CRBN蛋白的表达，因而可以用于制备治疗BCR‑ABL和/或CRBN阳性的白血病的药物，其中，n＝3的蛋白靶向降解嵌合分子具有优异的光致异构化活性，可以用于制备光照调控降解BCR‑ABL和/或CRBN蛋白的试剂或药物；本发明还提供了一种合成该系列蛋白靶向降解嵌合分子的方法。
• PROTEOLYSIS TARGETING CHIMERIC MOLECULE, PREPARATION METHOD, AND APPLICATION
  申请人：CHINA PHARMACEUTICAL UNIVERSITY

  公开号：US20210338695A1

  公开（公告）日：2021-11-04

  It discloses a proteolysis targeting chimeric molecule, a preparation method and an application thereof. The proteolysis targeting chimeric molecule provided by the disclosure can inhibit the expression of BCR-ABL and/or CRBN protein in BCR-ABL and/or CRBN positive leukemia K562 cells to varying degrees, and thus can be used to prepare drugs for treating BCR-ABL and/or CRBN positive leukemia, wherein the proteolysis targeting chimeric molecule with n=3 has excellent photo-isomerization activity, and can be used in preparation of the reagents or drugs for light-regulated degradation of BCR-ABL and/or CRBN protein. The disclosure also provides a method for synthesizing the series of proteolysis targeting chimeric molecules.