N-((7-methoxydibenzo[b,d]furan-1-yl)methyl)propan-2-amine | 1421007-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: N-((7-methoxydibenzo[b,d]furan-1-yl)methyl)propan-2-amine
• 英文别名: N-[(7-methoxydibenzofuran-1-yl)methyl]propan-2-amine
• CAS: 1421007-14-8
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: IGFHLBTUVSKECP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-((7-methoxydibenzo[b,d]furan-1-yl)methyl)propan-2-amine 在 吡啶 、 silver nitrate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 N-isopropyl-N-[(7-methoxydibenzo[b,d]furan-1-yl)methyl]-3-nitropropanamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents

  摘要：

  Facing the multifactorial nature of Alzheimer's disease, twelve dibenzofuran/carbazole derivatives, which can be considered as the D-ring opened analogs of galantamine, have been designed and synthesized as multifunctional anti-Alzheimer agents. In vitro tests revealed that compounds 3 and 5, which bear a nitrate moiety in the molecule, showed a potent inhibition activity towards AChE and compound 3 showed a good A beta 42 aggregation inhibitory activity. Moreover, 3 and 5 could also release a relative low concentration of NO in vitro and they did not show toxicity to neuronal cells, while exerted a neuroprotective effect against the A beta-induced toxicity. More importantly, compound 3 showed a significant spatial memory improving effect in vivo, and a good safety in the ex vivo toxicity study. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.035
• 作为产物：
  描述：

  4-methoxy-2-(3-methylphenoxy)-1-nitrobenzene 在 copper(I) oxide 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 硫酸 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 potassium iodide 、 sodium nitrite 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 水 为溶剂， 60.0 ℃ 、3.0 MPa 条件下， 反应 11.5h， 生成 N-((7-methoxydibenzo[b,d]furan-1-yl)methyl)propan-2-amine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents

  摘要：

  Facing the multifactorial nature of Alzheimer's disease, twelve dibenzofuran/carbazole derivatives, which can be considered as the D-ring opened analogs of galantamine, have been designed and synthesized as multifunctional anti-Alzheimer agents. In vitro tests revealed that compounds 3 and 5, which bear a nitrate moiety in the molecule, showed a potent inhibition activity towards AChE and compound 3 showed a good A beta 42 aggregation inhibitory activity. Moreover, 3 and 5 could also release a relative low concentration of NO in vitro and they did not show toxicity to neuronal cells, while exerted a neuroprotective effect against the A beta-induced toxicity. More importantly, compound 3 showed a significant spatial memory improving effect in vivo, and a good safety in the ex vivo toxicity study. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.035

文献信息

• Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents
  作者：Lei Fang、Xubin Fang、Shaohua Gou、Amelie Lupp、Isabell Lenhardt、Yanyan Sun、Zhangjian Huang、Yao Chen、Yihua Zhang、Christian Fleck

  DOI：10.1016/j.ejmech.2014.02.035

  日期：2014.4

  Facing the multifactorial nature of Alzheimer's disease, twelve dibenzofuran/carbazole derivatives, which can be considered as the D-ring opened analogs of galantamine, have been designed and synthesized as multifunctional anti-Alzheimer agents. In vitro tests revealed that compounds 3 and 5, which bear a nitrate moiety in the molecule, showed a potent inhibition activity towards AChE and compound 3 showed a good A beta 42 aggregation inhibitory activity. Moreover, 3 and 5 could also release a relative low concentration of NO in vitro and they did not show toxicity to neuronal cells, while exerted a neuroprotective effect against the A beta-induced toxicity. More importantly, compound 3 showed a significant spatial memory improving effect in vivo, and a good safety in the ex vivo toxicity study. (C) 2014 Elsevier Masson SAS. All rights reserved.