4-[[[4-[[Bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol | 1201916-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[[[4-[[Bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol
• CAS: 1201916-25-7
• 化学式: C₄₄H₅₂N₂O₁₂
• 分子量: 800.903
• InChiKey: KVSVXNRDYPZJNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  58
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1,4-苯二甲胺 、 丁香醛 在 三乙酰氧基硼氢化钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 123.0h， 以81%的产率得到4-[[[4-[[Bis[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]phenyl]methyl-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]amino]methyl]-2,6-dimethoxyphenol
  参考文献：
  名称：

  Synthesis and antioxidant properties of dendritic polyphenols

  摘要：

  Three dendritic polyphenols (generation 1) were synthesized: a syringaldehyde-based dendrimer (1), a vanillin-based dendrimer (2), and an iodinated vanillin-based dendrimer (3). They all showed strong antioxidant activity according to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical assay. The syringaldehyde dendrimer was twice and 10 times stronger than quercetin and Trolox, respectively. The vanillin-based dendrimer and its more hydrophobic iodinated derivative were also more potent antioxidants than quercetin and Trolox. The DPPH order of potency was 1 > 2, 3 > quercetin > Trolox. All three dendrimers also protected human LDL from free radical attack in a dose-dependent manner. Their order of free radical scavenging was 1 > 3 > 2 > quercetin > Trolox. The increased hydrophobic nature of the iodinated derivative may have contributed to its better LDL protection than 2. Protection of linoleic acid oxidation was studied by the beta-carotene-linoleate assay. Dendrimer 1 was clearly superior to the other antioxidants in protecting the fatty acid. In case of DNA protection against free radical damage, the order of activity was 1 > quercetin > 2 > 3, Trolox. Pro-oxidant effect on copper-induced DNA oxidation showed the following order: quercetin, Trolox > 1 > 2 > 3. Results of the study show that dendritic antioxidants, even at the generation 1 level, provide promising antioxidant properties for their potential use as drug candidates for diseases associated with oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.088

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
• Synthesis and antioxidant properties of dendritic polyphenols
  作者：Choon Young Lee、Ajit Sharma、Jae Eun Cheong、Julie L. Nelson

  DOI：10.1016/j.bmcl.2009.09.088

  日期：2009.11

  Three dendritic polyphenols (generation 1) were synthesized: a syringaldehyde-based dendrimer (1), a vanillin-based dendrimer (2), and an iodinated vanillin-based dendrimer (3). They all showed strong antioxidant activity according to the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical assay. The syringaldehyde dendrimer was twice and 10 times stronger than quercetin and Trolox, respectively. The vanillin-based dendrimer and its more hydrophobic iodinated derivative were also more potent antioxidants than quercetin and Trolox. The DPPH order of potency was 1 > 2, 3 > quercetin > Trolox. All three dendrimers also protected human LDL from free radical attack in a dose-dependent manner. Their order of free radical scavenging was 1 > 3 > 2 > quercetin > Trolox. The increased hydrophobic nature of the iodinated derivative may have contributed to its better LDL protection than 2. Protection of linoleic acid oxidation was studied by the beta-carotene-linoleate assay. Dendrimer 1 was clearly superior to the other antioxidants in protecting the fatty acid. In case of DNA protection against free radical damage, the order of activity was 1 > quercetin > 2 > 3, Trolox. Pro-oxidant effect on copper-induced DNA oxidation showed the following order: quercetin, Trolox > 1 > 2 > 3. Results of the study show that dendritic antioxidants, even at the generation 1 level, provide promising antioxidant properties for their potential use as drug candidates for diseases associated with oxidative stress. (C) 2009 Elsevier Ltd. All rights reserved.