7-[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptyloxy]-9-oxa-1-azaanthracen-10-one | 1333995-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptyloxy]-9-oxa-1-azaanthracen-10-one
• 英文别名: 8-[7-(1,2,3,4-Tetrahydroacridin-9-ylamino)heptoxy]chromeno[2,3-b]pyridin-5-one
• CAS: 1333995-52-0
• 化学式: C₃₂H₃₃N₃O₃
• 分子量: 507.632
• InChiKey: BFOOQYHXKGWIBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-胺-1,2,3,4-四氢盐酸氯酯 、 7-(7-bromoheptyloxy)-9-oxa-1-azaanthracen-10-one 在 四丁基硫酸氢铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 以7.6%的产率得到7-[7-(1,2,3,4-tetrahydroacridin-9-ylamino)heptyloxy]-9-oxa-1-azaanthracen-10-one
  参考文献：
  名称：

  Multi-target strategy to address Alzheimer’s disease: Design, synthesis and biological evaluation of new tacrine-based dimers

  摘要：

  The multifactorial nature of Alzheimer's disease (AD) offers us a textbook example where parental compounds, mostly marketed, are modified with the aim of improving and/or conferring two or even more biological activities to contrast or less frequently revert the disease's symptoms. This is the case of tacrine and its dimeric derivative bis(7)-tacrine which, for instance, paved the way for the development of a broad collection of very interesting homo- and heterodimeric structures, conceived in light of the emerging multi-target approach for AD-related drug discovery. As a contribution to the topic, we report here the design, synthesis and biological evaluation of 12 compounds referable to bis(7)-tacrine. In addition to the cholinesterase activity, some of the selected compounds (7-9 and 12) were capable of inhibiting the non-enzymatic function of AChE and/or showed a remarkable activity against BACE1. Thus, the present study outlines a series of newly synthesized molecules, structurally related to bis(7)-tacrine, endowed with extended biological profile in agreement with the emerging multi-target paradigm. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.004

文献信息

• Multi-target strategy to address Alzheimer’s disease: Design, synthesis and biological evaluation of new tacrine-based dimers
  作者：Stefano Rizzo、Alessandra Bisi、Manuela Bartolini、Francesca Mancini、Federica Belluti、Silvia Gobbi、Vincenza Andrisano、Angela Rampa

  DOI：10.1016/j.ejmech.2011.07.004

  日期：2011.9

  The multifactorial nature of Alzheimer's disease (AD) offers us a textbook example where parental compounds, mostly marketed, are modified with the aim of improving and/or conferring two or even more biological activities to contrast or less frequently revert the disease's symptoms. This is the case of tacrine and its dimeric derivative bis(7)-tacrine which, for instance, paved the way for the development of a broad collection of very interesting homo- and heterodimeric structures, conceived in light of the emerging multi-target approach for AD-related drug discovery. As a contribution to the topic, we report here the design, synthesis and biological evaluation of 12 compounds referable to bis(7)-tacrine. In addition to the cholinesterase activity, some of the selected compounds (7-9 and 12) were capable of inhibiting the non-enzymatic function of AChE and/or showed a remarkable activity against BACE1. Thus, the present study outlines a series of newly synthesized molecules, structurally related to bis(7)-tacrine, endowed with extended biological profile in agreement with the emerging multi-target paradigm. (C) 2011 Elsevier Masson SAS. All rights reserved.