N-(6-(3,4,5-trihydroxybenzamido)hexyl)-3,4,5-trihydroxybenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(6-(3,4,5-trihydroxybenzamido)hexyl)-3,4,5-trihydroxybenzamide
• 英文别名: N,N'-hexamethylenebis(3,4,5-trihydroxybenzamide)；N,N'-bisgalloyl 1,6-diaminohexane；N,N'-1,6-hexanediylbis(3,4,5-trihydroxybenzamide)；3,4,5-trihydroxy-N-[6-[(3,4,5-trihydroxybenzoyl)amino]hexyl]benzamide
• 化学式: C₂₀H₂₄N₂O₈
• 分子量: 420.419
• InChiKey: UMVKGIFAQHIGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  180
• 氢给体数：
  8
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲酸 在 五氯化磷 、 三溴化硼 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 N-(6-(3,4,5-trihydroxybenzamido)hexyl)-3,4,5-trihydroxybenzamide
  参考文献：
  名称：

  Synthesis and in Vitro Evaluation of Two Progressive Series of Bifunctional Polyhydroxybenzamide Catechol-O-methyltransferase Inhibitors

  摘要：

  Two progressive series of molecules with two polyhydroxybenzamide substructures were synthesized and tested as potential inhibitors of catechol-O-methyltransferase (COMT). These compounds were designed for the purpose of enhanced enzyme binding with duplicated substructures separated by a linker section of various lengths. Our results show that potency and mode of inhibition observed with the ''bifunctional'' compounds were a reflection of their bifunctional nature. Furthermore, potency and mode of inhibition were dependent on the length of the linker section. Of the assayed compounds, the optimum linker was found to be diaminopropane. For example, N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide) and N,N'-1,3-propanediylbis(3,4,5-trihydroxybenzamide) demonstrated strong inhibitory action against COMT, with apparent K-i values of 0.3 and 6.0 mu M, respectively.

  DOI：

  10.1021/jm9605187

文献信息

• Structure-Activity Relationship of Bis-Galloyl Derivatives Related to (-)-Epigallocatechin Gallate
  作者：Kosuke Dodo、Taro Minato、Yuichi Hashimoto

  DOI：10.1248/cpb.57.190

  日期：——

  Green tea and (−)-epigallocatechin gallate (EGCG: one of main components of green tea) are well known to have preventive activities against human cancers. Previously, using a galloyl group as a core structure derived from EGCG, we developed alkyl gallate and gallamide derivatives, which showed strong antiproliferative activity towards human leukemia HL-60 cells by inducing apoptosis. Here, as a further structural development study, we planned to introduce an additional galloyl group into alkyl gallates and gallamides. According to this strategy, various bisgallate and bisgallamide derivatives were synthesized and tested for antiproliferative activity towards HL-60 cells. In gallamide derivatives having a short alkyl chain, the additional galloyl group enhanced the antiproliferative activity. In contrast, in the gallate derivatives, the additional galloyl group had no effect on the antiproliferative activity.

  绿茶和（−）-表没食子酸没食子酯（EGCG：绿茶的主要成分之一）众所周知对人类癌症具有预防活性。之前，我们利用从EGCG衍生的没食子酰基作为核心结构，开发了烷基没食子酸酯和没食子酰胺衍生物，这些衍生物通过诱导细胞凋亡对人类白血病HL-60细胞表现出强的抗增殖活性。在这里，作为进一步的结构开发研究，我们计划在烷基没食子酸酯和没食子酰胺中引入额外的没食子酰基。根据这一策略，合成了多种双没食子酸酯和双没食子酰胺衍生物，并测试其对HL-60细胞的抗增殖活性。在具有短烷基链的没食子酰胺衍生物中，额外的没食子酰基增强了抗增殖活性。相反，在没食子酸酯衍生物中，额外的没食子酰基对抗增殖活性没有影响。
• 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。
• 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.
• Synthesis and <i>in Vitro</i> Evaluation of Two Progressive Series of Bifunctional Polyhydroxybenzamide Catechol-<i>O</i>-methyltransferase Inhibitors
  作者：Sharon E. Brevitt、Eng Wui Tan

  DOI：10.1021/jm9605187

  日期：1997.6.1

  Two progressive series of molecules with two polyhydroxybenzamide substructures were synthesized and tested as potential inhibitors of catechol-O-methyltransferase (COMT). These compounds were designed for the purpose of enhanced enzyme binding with duplicated substructures separated by a linker section of various lengths. Our results show that potency and mode of inhibition observed with the ''bifunctional'' compounds were a reflection of their bifunctional nature. Furthermore, potency and mode of inhibition were dependent on the length of the linker section. Of the assayed compounds, the optimum linker was found to be diaminopropane. For example, N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide) and N,N'-1,3-propanediylbis(3,4,5-trihydroxybenzamide) demonstrated strong inhibitory action against COMT, with apparent K-i values of 0.3 and 6.0 mu M, respectively.