(4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol)) | 1246672-86-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol))
• 英文别名: 4-[[(4-Hydroxy-3,5-dimethoxyphenyl)methyl-prop-2-ynylamino]methyl]-2,6-dimethoxyphenol；4-[[(4-hydroxy-3,5-dimethoxyphenyl)methyl-prop-2-ynylamino]methyl]-2,6-dimethoxyphenol
• CAS: 1246672-86-5
• 化学式: C₂₁H₂₅NO₆
• 分子量: 387.433
• InChiKey: OHMSZDOIHXEWFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3,3′-((2-((3-azido-2-hydroxypropoxy)methyl)-2-ethylpropane-1,3-diyl)bis(oxy))bis(1-azidopropan-2-ol)) 、 (4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol)) 在 铜 作用下， 以 四氢呋喃 为溶剂， 77.0~85.0 ℃ 、1.72 MPa 条件下， 反应 8.0h， 以77%的产率得到4-[[[1-[3-[2,2-Bis[[3-[4-[[bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]triazol-1-yl]-2-hydroxypropoxy]methyl]butoxy]-2-hydroxypropyl]triazol-4-yl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol
  参考文献：
  名称：

  Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers

  摘要：

  Syringaldehyde- and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cydoaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. To produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (<5% yield). However, they were an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as the background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 mu M in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.

  DOI：

  10.1021/jo401603d
• 作为产物：
  描述：

  炔丙胺 、 丁香醛 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 生成 (4,4'-((prop-2-yn-1-ylazanediyl)bis(methylene))bis(2,6-dimethoxyphenol))
  参考文献：
  名称：

  给电子基团对多酚基抗氧化剂树枝状聚合物的影响。

  摘要：

  许多研究报告了抗氧化剂在人类疾病中的有益作用。在其生物学效应中，大多数抗氧化剂清除体内的反应性自由基，从而减少与许多疾病的发病机理相关的氧化应激。抗氧化剂树状聚合物是最近报道的一类新的有效抗氧化剂化合物。在这项研究中，合成六种带有或不带有供电子基团（甲氧基）的多酚类抗氧化剂树状大分子，以阐明供电子基团（EDG）对其抗氧化活性的影响。用炔丙基胺将丁醛（2个邻甲氧基），香兰素（1个邻甲氧基）和4-羟基苯甲醛（0个甲氧基）衍生化，以形成树枝状聚合物的结构单元。六个树枝状大分子都含有聚醚核，它们是通过将季戊四醇和甲基α-d-吡喃葡萄糖苷连接到内部制备的间隔单元上而合成的。为了制备第1代抗氧化剂树状聚合物，使用微波能和粒状金属铜催化剂通过炔-叠氮化物1,3-环加成点击化学将核和构件连接在一起。这些反应条件导致没有铜污染的目标树枝状聚合物的高收率。根据DPPH抗氧化剂分析，与丁香醛和香兰素相比，用丁香

  DOI：

  10.1016/j.biochi.2015.02.001

文献信息

• DENDRITIC NANO-ANTIOXIDANTS
  申请人：Lee Choon Young

  公开号：US20100247439A1

  公开（公告）日：2010-09-30

  Provided are dendritic nano-antioxidant compounds according to Formula I, which may further comprise active agents covalently or non-covalently attached. Further provided are compositions comprising the disclosed compounds. Also disclosed are cosmetic compositions and dietary supplements comprising the compounds according to Formula I. The invention additionally provides methods of reducing free radicals or oxidative stress in a cell, a method of treating a subject, and a method of treating a condition comprising administering the compounds according to Formula I.

  本发明提供了公式I的树突型纳米抗氧化化合物，该化合物可以进一步包含共价或非共价附着的活性剂。还提供了包含所述化合物的组合物。还公开了包含公式I的化合物的化妆品组合物和膳食补充剂。此外，本发明还提供了减少细胞中自由基或氧化应激的方法，治疗受试者的方法以及治疗包括给予公式I的化合物的病症的方法。
• US8895032B2
  申请人：——

  公开号：US8895032B2

  公开（公告）日：2014-11-25
• Effect of electron donating groups on polyphenol-based antioxidant dendrimers
  作者：Choon Young Lee、Cyprien N. Nanah、Rich A. Held、Amanda R. Clark、Uyen G.T. Huynh、Marina C. Maraskine、Rebecca L. Uzarski、John McCracken、Ajit Sharma

  DOI：10.1016/j.biochi.2015.02.001

  日期：2015.4

  EDG groups. Similar results were obtained when the dendrimers were used to protect DNA and human LDL against organic carbon and nitrogen-based free radicals. In addition, the antioxidant dendrimers did not show any pro-oxidant activity on DNA in the presence of physiological amounts of copper. Although the dendrimers showed potent antioxidant activities against carbon and nitrogen free radicals, EPR

  许多研究报告了抗氧化剂在人类疾病中的有益作用。在其生物学效应中，大多数抗氧化剂清除体内的反应性自由基，从而减少与许多疾病的发病机理相关的氧化应激。抗氧化剂树状聚合物是最近报道的一类新的有效抗氧化剂化合物。在这项研究中，合成六种带有或不带有供电子基团（甲氧基）的多酚类抗氧化剂树状大分子，以阐明供电子基团（EDG）对其抗氧化活性的影响。用炔丙基胺将丁醛（2个邻甲氧基），香兰素（1个邻甲氧基）和4-羟基苯甲醛（0个甲氧基）衍生化，以形成树枝状聚合物的结构单元。六个树枝状大分子都含有聚醚核，它们是通过将季戊四醇和甲基α-d-吡喃葡萄糖苷连接到内部制备的间隔单元上而合成的。为了制备第1代抗氧化剂树状聚合物，使用微波能和粒状金属铜催化剂通过炔-叠氮化物1,3-环加成点击化学将核和构件连接在一起。这些反应条件导致没有铜污染的目标树枝状聚合物的高收率。根据DPPH抗氧化剂分析，与丁香醛和香兰素相比，用丁香
• Copper-Granule-Catalyzed Microwave-Assisted Click Synthesis of Polyphenol Dendrimers
  作者：Choon Young Lee、Rich Held、Ajit Sharma、Rom Baral、Cyprien Nanah、Dan Dumas、Shannon Jenkins、Samik Upadhaya、Wenjun Du

  DOI：10.1021/jo401603d

  日期：2013.11.15

  Syringaldehyde- and vanillin-based antioxidant dendrimers were synthesized via microwave-assisted alkyne-azide 1,3-dipolar cydoaddition using copper granules as a catalyst. The use of Cu(I) as a catalyst resulted in copper contaminated dendrimers. To produce copper-free antioxidant dendrimers for biological applications, Cu(I) was substituted with copper granules. Copper granules were ineffective at both room temperature and under reflux conditions (<5% yield). However, they were an excellent catalyst when dendrimer synthesis was performed under microwave irradiation, giving yields up to 94% within 8 h. ICP-mass analysis of the antioxidant dendrimers obtained with this method showed virtually no copper contamination (9 ppm), which was the same as the background level. The synthesized antioxidants, free from copper contamination, demonstrated potent radical scavenging with IC50 values of less than 3 mu M in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. In comparison, dendrimers synthesized from Cu(I)-catalyzed click chemistry showed a high level of copper contamination (4800 ppm) and no detectable antioxidant activity.