4-[(3-Aminopropylamino)methyl]-2-methoxyphenol | 1178285-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-[(3-Aminopropylamino)methyl]-2-methoxyphenol
• CAS: 1178285-73-8
• 化学式: C₁₁H₁₈N₂O₂
• 分子量: 210.276
• InChiKey: FLSMPEBFNMFZGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-二甲氧基-1,4-苯醌 、 4-[(3-Aminopropylamino)methyl]-2-methoxyphenol 以 乙醇 为溶剂， 生成 2,5-Bis[3-[(4-hydroxy-3-methoxyphenyl)methylamino]propylamino]cyclohexa-2,5-diene-1,4-dione
  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
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 4-[(3-Aminopropylamino)methyl]-2-methoxyphenol
  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

• 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.