N-(4-aminobutyl)benzofuran-2-carboxamide

• 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-(4-aminobutyl)benzofuran-2-carboxamide
• 英文别名: N-(4-aminobutyl)-1-benzofuran-2-carboxamide
• 化学式: C₁₃H₁₆N₂O₂
• mdl: MFCD13166066
• 分子量: 232.282
• InChiKey: RPSAVXWOVCYBAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  68.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-甲氧基-2-氧代-2H-色烯-3-羧酸 、 N-(4-aminobutyl)benzofuran-2-carboxamide 在 N-甲基吗啉 、 1-丙基磷酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Development of coumarin–benzofuran hybrids as versatile multitargeted compounds for the treatment of Alzheimer’s Disease

  摘要：

  Alzheimer’s disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin–benzofuran hybrids have been designed and screened as anti‐Alzheimer’s disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug‐likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid‐β (Aβ) self‐aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug‐like moieties as efficient anti‐AD agents.

  DOI：

  10.1111/cbdd.13316
• 作为产物：
  描述：

  水杨醛 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-(4-aminobutyl)benzofuran-2-carboxamide
  参考文献：
  名称：

  新型他克林-苯并呋喃杂种作为治疗阿尔茨海默氏病的潜在多靶点药物候选物

  摘要：

  抽象的 为寻求对抗阿尔茨海默氏病（AD）的多靶点药物的广泛兴趣，基于众所周知的乙酰胆碱酯酶（AChE）抑制剂他克林（TAC）的重新定位，设计并开发了一系列新的杂种与苯并呋喃（BF）衍生物偶联。BF框架旨在赋予共轭分子以抑制AChE（双峰方式）和淀粉样β肽聚集的能力，此外还为具有羟基的杂合体提供金属（Fe，Cu）螯合能力和伴随的额外抗氧化活性。代换。新的TAC-BF共轭物显示出非常好的AChE抑制活性（亚微摩尔范围），并且具有抑制自身和Cu介导的Aβ聚集的能力，这取决于每个主要部分的接头大小和取代基。1-42诱导的毒性。结构-活性关系分析提供了最佳结构参数的见解，以考虑到未来在AD治疗中的潜在应用。

  DOI：

  10.1080/14756366.2019.1689237

文献信息

• Novel tacrine–benzofuran hybrids as potential multi-target drug candidates for the treatment of Alzheimer’s Disease
  作者：Gaia Fancellu、Karam Chand、Daniel Tomás、Elisabetta Orlandini、Luca Piemontese、Diana F. Silva、Sandra M. Cardoso、Sílvia Chaves、M. Amélia Santos

  DOI：10.1080/14756366.2019.1689237

  日期：2020.1.1

  conjugates showed very good activity for AChE inhibition (sub-micromolar range) and good capacity for the inhibition of self- and Cu-mediated Aβ aggregation, with dependence on the linker size and substituent groups of each main moiety. Neuroprotective effects were also found for the compounds through viability assays of neuroblastoma cells, after Aβ1-42 induced toxicity. Structure-activity relationship analysis

  抽象的 为寻求对抗阿尔茨海默氏病（AD）的多靶点药物的广泛兴趣，基于众所周知的乙酰胆碱酯酶（AChE）抑制剂他克林（TAC）的重新定位，设计并开发了一系列新的杂种与苯并呋喃（BF）衍生物偶联。BF框架旨在赋予共轭分子以抑制AChE（双峰方式）和淀粉样β肽聚集的能力，此外还为具有羟基的杂合体提供金属（Fe，Cu）螯合能力和伴随的额外抗氧化活性。代换。新的TAC-BF共轭物显示出非常好的AChE抑制活性（亚微摩尔范围），并且具有抑制自身和Cu介导的Aβ聚集的能力，这取决于每个主要部分的接头大小和取代基。1-42诱导的毒性。结构-活性关系分析提供了最佳结构参数的见解，以考虑到未来在AD治疗中的潜在应用。
• Development of coumarin–benzofuran hybrids as versatile multitargeted compounds for the treatment of Alzheimer’s Disease
  作者：Asha Hiremathad、Karam Chand、Rangappa S. Keri

  DOI：10.1111/cbdd.13316

  日期：2018.8

  Alzheimer’s disease (AD), the most common cause of dementia, is a neurodegenerative disorder characterized by progressive deterioration of memory and cognition. The evidenced multifactorial nature of AD has been considered the main reason for the absence of cure so far. Therefore, the development of novel hybrids to treat the disease is very much essential. Focusing on this, a novel series of coumarin–benzofuran hybrids have been designed and screened as anti‐Alzheimer’s disease agents. The strategy is to obtain an effective mimetic of donepezil, which is acetylcholinesterase inhibitor. Herein, the two main scaffolds namely coumarin and benzofuran are known pharmacophore moieties and we have performed their molecular design, pharmacokinetic descriptor studies for drug‐likeliness. Further, in vitro studies such as antioxidant capacity, acetylcholinesterase (AChE) inhibition and amyloid‐β (Aβ) self‐aggregation inhibition have also been performed. Most importantly, these studies revealed that the newly synthesized hybrids can be versatile and promising drug‐like moieties as efficient anti‐AD agents.