N,N',N''-triscaffeoyl tris-(2-aminoethyl)amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N',N''-triscaffeoyl tris-(2-aminoethyl)amine
• 英文别名: N,N'-1,3-propanediylbis(3,4-dihydroxybenzamide)；N,N''-1,3-Propanediylbis(3,4-dihydroxybenzamide)；N-[3-[(3,4-dihydroxybenzoyl)amino]propyl]-3,4-dihydroxybenzamide
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: ORSDFVQUISPDOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  藜芦酸 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,N',N''-triscaffeoyl tris-(2-aminoethyl)amine
  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

• 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。
• [EN] PHARMACOLOGICAL AGENTS FOR TREATING CONDITIONS OF THE EYE<br/>[FR] AGENTS PHARMACOLOGIQUES POUR TRAITER DES PATHOLOGIES OCULAIRES
  申请人：[en]PLEX PHARMACEUTICALS, INC.

  公开号：WO2022104383A1

  公开（公告）日：2022-05-19

  Provided are compounds useful for treating, preventing, reducing the occurrence of, slowing the progression of, or reducing, ameliorating, or alleviating the symptoms associated with a condition selected from the group consisting of: presbyopia, cataract, transthyretin (TTR)- associated amyloidosis, myopia, or other conditions or disorders associated with the eye, including COMT inhibitors and pro-drugs thereof, and methods of using these compounds.
• 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.