2,5-bis-[6-(4-hydroxy-3-methoxy-benzylamino)-hexylamino]-[1,4]benzoquinone | 1130608-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-bis-[6-(4-hydroxy-3-methoxy-benzylamino)-hexylamino]-[1,4]benzoquinone
• 英文别名: 2,5-Bis[6-[(4-hydroxy-3-methoxyphenyl)methylamino]hexylamino]cyclohexa-2,5-diene-1,4-dione
• CAS: 1130608-89-7
• 化学式: C₃₄H₄₈N₄O₆
• 分子量: 608.778
• InChiKey: ASJXQHKDXMZZHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  44
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苄基(6-氨基己基)氨基甲酸酯盐酸盐(1:1) 在 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 2,5-bis-[6-(4-hydroxy-3-methoxy-benzylamino)-hexylamino]-[1,4]benzoquinone
  参考文献：
  名称：

  Multitargeted drugs discovery: Balancing anti-amyloid and anticholinesterase capacity in a single chemical entity

  摘要：

  Memoquin (1) is a lead compound multitargeted against Alzheimer's disease (AD). It is an AChE inhibitor, free-radical scavenger, and inhibitor of amyloid-beta (A beta) aggregation. A new series of 1 derivatives was designed and synthesized by linking its 2,5-diamino-benzoquinone core with motifs that are present in the structure of known amyloid binding agents like curcumin, the benzofuran derivative SKF64346, or the benzothiazole bearing compounds KHG21834 and BTA-1. The weaker AChE inhibitory potencies and the concomitant nearly equipotent anti-amyloid activities of the new compounds with respect to 1 resulted in a more balanced biological profile against both targets. Selected compounds turned out to be effective A beta aggregation inhibitors in a cell-based assay. By properly combining two or more distinct pharmacological properties in a molecule, we can achieve greater effectiveness compared to single-targeted drugs for investigating AD. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.093

文献信息

• [EN] ORGANIC COMPOUNDS USEFUL FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES, USES AND METHODS FOR THE PREPARATION THEREOF<br/>[FR] COMPOSÉS ORGANIQUES UTILES POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES, LEURS UTILISATIONS ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：UNIV BOLOGNA ALMA MATER

  公开号：WO2009034457A1

  公开（公告）日：2009-03-19

  Compounds having a general formula (I) are used for the treatment of neurodegenerative diseases, wherein at least one of R1 ed R8 is chosen from the group consisting of (II), (III), (V), (VI), (XVII).

  具有通式（I）的化合物用于治疗神经退行性疾病，其中R1和R8中至少有一个选择自由基组（II）、（III）、（V）、（VI）、（XVII）中的一种。
• Multitargeted drugs discovery: Balancing anti-amyloid and anticholinesterase capacity in a single chemical entity
  作者：Maria Laura Bolognesi、Manuela Bartolini、Andrea Tarozzi、Fabiana Morroni、Federica Lizzi、Andrea Milelli、Anna Minarini、Michela Rosini、Patrizia Hrelia、Vincenza Andrisano、Carlo Melchiorre

  DOI：10.1016/j.bmcl.2010.12.093

  日期：2011.5

  Memoquin (1) is a lead compound multitargeted against Alzheimer's disease (AD). It is an AChE inhibitor, free-radical scavenger, and inhibitor of amyloid-beta (A beta) aggregation. A new series of 1 derivatives was designed and synthesized by linking its 2,5-diamino-benzoquinone core with motifs that are present in the structure of known amyloid binding agents like curcumin, the benzofuran derivative SKF64346, or the benzothiazole bearing compounds KHG21834 and BTA-1. The weaker AChE inhibitory potencies and the concomitant nearly equipotent anti-amyloid activities of the new compounds with respect to 1 resulted in a more balanced biological profile against both targets. Selected compounds turned out to be effective A beta aggregation inhibitors in a cell-based assay. By properly combining two or more distinct pharmacological properties in a molecule, we can achieve greater effectiveness compared to single-targeted drugs for investigating AD. (C) 2010 Elsevier Ltd. All rights reserved.