tris-[2-(3',4',5'-trihydroxybenzamido)ethyl]amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: tris-[2-(3',4',5'-trihydroxybenzamido)ethyl]amine
• 英文别名: tris[2-(3',4',5'-trihydroxybenzamido)ethyl]amine；N,N',N''-trisgalloyl tris-(2-aminoethyl) amine；N,N',N''-trigalloyl tris-(2-aminoethyl)amine；N-[2-[bis[2-[(3,4,5-trihydroxybenzoyl)amino]ethyl]amino]ethyl]-3,4,5-trihydroxy-benzamide；N-[2-[bis[2-[(3,4,5-trihydroxybenzoyl)amino]ethyl]amino]ethyl]-3,4,5-trihydroxybenzamide
• 化学式: C₂₇H₃₀N₄O₁₂
• 分子量: 602.555
• InChiKey: TXNJOUQFOJQLMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  273
• 氢给体数：
  12
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  N,Na(2),Na(2)a(2)-(Nitrilotri-2,1-ethanediyl)tris[3,4,5-trimethoxybenzamide] 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到tris-[2-(3',4',5'-trihydroxybenzamido)ethyl]amine
  参考文献：
  名称：

  Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors

  摘要：

  Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV.Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties.The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.033

文献信息

• Simple, Clean and Highly Efficient Synthesis of Polyphenolic Amides Catalysed by Ferric Exchanged Montmorillonite
  作者：Dhrubajyoti Mahanta、Jyotirekha G. Handique

  DOI：10.2174/157017811799304241

  日期：2011.11.1

  A mild, efficient and highly convenient protocol is reported for the synthesis of a series of polyphenolic amides using ferric exchanged montmorillonite as a strong solid acid catalyst. This heterogeneous catalyst has an advantage of a strikingly simple work up procedure over conventional homogeneous acids. The catalyst is recoverable and recyclable.

  报告采用铁交换蒙脱石作为强固酸催化剂，合成了一系列多酚酰胺，该方法温和、高效、操作简便。与传统的均相酸催化剂相比，这种异相催化剂的优点是操作过程非常简单。催化剂可回收和循环使用。
• Synthetic Gallic Acid Derivatives as Models for a Comprehensive Study of Antioxidant Activity
  作者：Florence Belin、Philippe Barthélémy、Karine Ruiz、Jean Michel Lacombe、Bernard Pucci

  DOI：10.1002/hlca.200390053

  日期：2003.2

  The synthesis and antioxidant efficiencies of amphiphilic gallic acid derivatives are reported. To specify the impact of chemical structure on the antioxidant efficiency, several structural modifications of gallic acid were performed. The following structural features were chosen: i) introduction of hydrophobic or hydrophilic residues on the gallic acid and the type of their linkage, ii) the hydrophilic

  报道了两亲没食子酸衍生物的合成和抗氧化剂效率。为了说明化学结构对抗氧化剂效率的影响，对没食子酸进行了几种结构修饰。选择了以下结构特征：i）在没食子酸上引入疏水或亲水残基以及它们的连接类型，ii）整个分子的亲水性和/或亲脂性。所制备的不同系列的理化研究表明，该多酚的抗氧化效率明显取决于与亲水和疏水部分的连接性质。始终需要推挽效应，酯或酰胺键似乎很适合提高抗氧化剂的效率。第二，观察到在所施加的氧化条件下，亲水性和/或亲脂性极大地影响了没食子酸衍生物的抗氧化活性。获得的结果与极性悖论相符，疏水性衍生物抑制了水相中的氧化，而亲水性产品则无效。
• Handique, Jyotirekha G.; Mahanta, Dhrubajyoti; Devi, Archana, Letters in Organic Chemistry, 2013, vol. 10, # 1, p. 53 - 59
  作者：Handique, Jyotirekha G.、Mahanta, Dhrubajyoti、Devi, Archana、Boruah, Manas P.

  DOI：——

  日期：——
• Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
  作者：Eva Rivero-Buceta、Paula Carrero、Elisa G. Doyagüez、Andrés Madrona、Ernesto Quesada、María José Camarasa、María Jesús Peréz-Pérez、Pieter Leyssen、Jan Paeshuyse、Jan Balzarini、Johan Neyts、Ana San-Félix

  DOI：10.1016/j.ejmech.2015.01.033

  日期：2015.3

  Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV.Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties.The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.