N,N',N"-tris(3,4,5-trihydroxybenzoyl)spermidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N',N"-tris(3,4,5-trihydroxybenzoyl)spermidine
• 英文别名: 3,4,5-trihydroxy-N-[4-[(3,4,5-trihydroxybenzoyl)-[3-[(3,4,5-trihydroxybenzoyl)amino]propyl]amino]butyl]benzamide
• 化学式: C₂₈H₃₁N₃O₁₂
• 分子量: 601.567
• InChiKey: GXEQDEYMUKRWKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  261
• 氢给体数：
  11
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3,4,5-trimethoxy-N-[4-[(3,4,5-trimethoxybenzoyl)-[3-[(3,4,5-trimethoxybenzoyl)amino]propyl]amino]butyl]benzamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到N,N',N"-tris(3,4,5-trihydroxybenzoyl)spermidine
  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

• 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.