4-(2,3-dihydrobenzo[f][1,4]oxazepin-4(5H)-yl)butan-1-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-(2,3-dihydrobenzo[f][1,4]oxazepin-4(5H)-yl)butan-1-amine
• 英文别名: 4-(3,5-dihydro-2H-1,4-benzoxazepin-4-yl)butan-1-amine
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: QSFIXYCWLCKEMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,3-dihydrobenzo[f][1,4]oxazepin-4(5H)-yl)butan-1-amine 、 水杨酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 以50.4%的产率得到N-(4-(2,3-dihydrobenzo[f][1,4]oxazepin-4(5H)-yl)butyl)-2-hydroxybenzamide
  参考文献：
  名称：

  新型水杨酰胺衍生物作为有效的多功能药物，可治疗阿尔茨海默氏病：设计，合成和生物学评估。

  摘要：

  设计，合成和评估了一系列水杨酰胺衍生物，作为治疗阿尔茨海默氏病的多功能药物。体外测定表明，大多数衍生物是选择性的AChE抑制剂。他们表现出良好的自我和Cu2 +诱导的Aβ1-42聚集的抑制活性，以及​​显着的抗氧化活性。其中，化合物15b显示出对RatAChE和EeAChE的良好抑制活性，IC 50值分别为10.4μM和15.2μM。此外，15b表现出较高的抗氧化活性（2.46 Trolox当量），良好的自我和Cu2 +诱导的Aβ1-42聚集抑制能力（在25.0μM时分别为42.5％和31.4％）以及对自我和Cu2 +诱导的Aβ1的中等分解能力。 -42聚集原纤维（25μM时分别为23.4％和27.0％）。此外，图15b还显示了生物金属螯合能力，抗神经炎能力和BBB通透性。这些多功能特性表明，化合物15b值得选择用于进一步的药代动力学，毒性和行为研究，以测试其在AD治疗中的潜力。

  DOI：

  10.1016/j.bioorg.2018.11.022
• 作为产物：
  描述：

  2,3,4,5-四氢苯并[f][1,4]氧氮杂卓 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 4-(2,3-dihydrobenzo[f][1,4]oxazepin-4(5H)-yl)butan-1-amine
  参考文献：
  名称：

  Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer’s disease

  摘要：

  A series of chromone-2-carboxamido-alkylbenzylamines were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good multifunctional activities. Among them, compound 49 displayed excellent inhibitory potency toward acetylcholinesterase (AChE), moderate anti-oxidative activity, selective biometal chelating, and possessed good inhibitory effects on self-induced and Cu2+-induced Ab aggregation. Both kinetic analysis of AChE inhibition and molecular modeling study indicated that 49 was a mixed-type inhibitor, binding simultaneously to the catalytic active site and peripheral anionic site of AChE. These results suggested that 49 might be a potential multifunctional agent for AD treatment. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.042

文献信息

• Discovery of novel 2,5-dihydroxyterephthalamide derivatives as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Qing Song、Yan Li、Zhongcheng Cao、Hongyan Liu、Chaoquan Tian、Ziyi Yang、Xiaoming Qiang、Zhenghuai Tan、Yong Deng

  DOI：10.1016/j.bmc.2018.11.015

  日期：2018.12

  excellent inhibitory effects on self-induced Aβ1–42 aggregation (IC50 = 3.05 μM) and Cu2+-induced Aβ1–42 aggregation (71.7% at 25.0 μM), and displayed significant disaggregation ability to self- and Cu2+-induced Aβ1–42 aggregation fibrils (75.2% and 77.2% at 25.0 μM, respectively). Furthermore, 9d also showed biometal chelating abilities, antioxidant activity, anti-neuroinflammatory activities and appropriate

  设计，合成和评估了一系列2,5-二羟基对苯二甲酰胺衍生物，并将其作为治疗阿尔茨海默氏病的多功能药物。体外测定表明大多数衍生物表现出良好的多功能活性。其中，化合物9d对大鼠AChE和Ee AChE均表现出最佳的抑制活性（IC 50 分别为0.56μM和5.12μM）。此外，图9D显示对自感应的优良抑制作用β 1-42聚集（IC 50  = 3.05μM）和Cu 2+诱导的阿β 1-42聚合（在25.0μM71.7％），并将其显示给自我显著分解能力和Cu 2+诱导的阿β 1-42聚集原纤维（75.2％和77.2％在25.0μM，分别地）。此外，9d还显示出生物金属螯合能力，抗氧化活性，抗神经炎活性和适当的BBB通透性。这些多功能特性突显了9d作为有希望的候选物，可用于针对AD的新药开发的进一步研究。
• Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer’s disease
  作者：Qiang Liu、Xiaoming Qiang、Yan Li、Zhipei Sang、Yuxing Li、Zhenghuai Tan、Yong Deng

  DOI：10.1016/j.bmc.2015.01.042

  日期：2015.3

  A series of chromone-2-carboxamido-alkylbenzylamines were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good multifunctional activities. Among them, compound 49 displayed excellent inhibitory potency toward acetylcholinesterase (AChE), moderate anti-oxidative activity, selective biometal chelating, and possessed good inhibitory effects on self-induced and Cu2+-induced Ab aggregation. Both kinetic analysis of AChE inhibition and molecular modeling study indicated that 49 was a mixed-type inhibitor, binding simultaneously to the catalytic active site and peripheral anionic site of AChE. These results suggested that 49 might be a potential multifunctional agent for AD treatment. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel salicylamide derivatives as potent multifunctional agents for the treatment of Alzheimer's disease: Design, synthesis and biological evaluation
  作者：Qing Song、Yan Li、Zhongcheng Cao、Xiaoming Qiang、Zhenghuai Tan、Yong Deng

  DOI：10.1016/j.bioorg.2018.11.022

  日期：2019.3

  A series of salicylamide derivatives were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease. In vitro assays demonstrated that most of the derivatives were selective AChE inhibitors. They showed good inhibitory activities of self- and Cu2+-induced Aβ1-42 aggregation, and significant antioxidant activities. Among them, compound 15b exhibited good

  设计，合成和评估了一系列水杨酰胺衍生物，作为治疗阿尔茨海默氏病的多功能药物。体外测定表明，大多数衍生物是选择性的AChE抑制剂。他们表现出良好的自我和Cu2 +诱导的Aβ1-42聚集的抑制活性，以及​​显着的抗氧化活性。其中，化合物15b显示出对RatAChE和EeAChE的良好抑制活性，IC 50值分别为10.4μM和15.2μM。此外，15b表现出较高的抗氧化活性（2.46 Trolox当量），良好的自我和Cu2 +诱导的Aβ1-42聚集抑制能力（在25.0μM时分别为42.5％和31.4％）以及对自我和Cu2 +诱导的Aβ1的中等分解能力。 -42聚集原纤维（25μM时分别为23.4％和27.0％）。此外，图15b还显示了生物金属螯合能力，抗神经炎能力和BBB通透性。这些多功能特性表明，化合物15b值得选择用于进一步的药代动力学，毒性和行为研究，以测试其在AD治疗中的潜力。