N-(4-hydroxycoumarin-3-yl)acrylamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(4-hydroxycoumarin-3-yl)acrylamide
• 英文别名: N-(4-Hydroxycoumarin-3-yl)acrylamide (3)；N-(4-hydroxy-2-oxochromen-3-yl)prop-2-enamide
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: BDBIVFHRDBXBPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基-3-硝基香豆素 在 吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-(4-hydroxycoumarin-3-yl)acrylamide
  参考文献：
  名称：

  Evaluation of Trypanocidal and Antioxidant Activities of a Selected Series of 3-amidocoumarins

  摘要：

  背景：由于全球化，被忽视的疾病变得越来越普遍。这激发了针对恰加斯病等寄生虫病治疗新药开发的活跃研究。 目的：为了寻找新的杀锥虫剂，我们报告了一系列新型3-酰胺香豆素（有无羟基取代基在香豆素环的4位）的体外评估。 方法：进行了电化学和生物学测试，以评估这些化合物的抗氧化和杀锥虫潜力，并更好地理解其活性涉及的机制。 结果：大多数研究化合物对epimastigote和trypomastigote形式都显示出高度的杀锥虫活性，IC50值在低微摩尔范围内。其中一些化合物比参考化合物硝呋莫司具有更高的活性和选择性。 结论：化合物2是该系列中最活跃的，对小鼠RAW 264.7巨噬细胞也没有细胞毒性。进行了电化学和自由基清除实验，为最佳衍生物的特性提供了新的信息，并展示了新型3-酰胺香豆素的潜在治疗应用。

  DOI：

  10.2174/1573406414666180419113437

文献信息

• Development of novel adenosine receptor ligands based on the 3-amidocoumarin scaffold
  作者：Maria J. Matos、Santiago Vilar、Sonja Kachler、Maria Celeiro、Saleta Vazquez-Rodriguez、Lourdes Santana、Eugenio Uriarte、George Hripcsak、Fernanda Borges、Karl-Norbert Klotz

  DOI：10.1016/j.bioorg.2015.05.008

  日期：2015.8

  With the aim of finding new adenosine receptor (AR) ligands presenting the 3-amidocoumarin scaffold, a study focusing on the discovery of new chemical entities was carried out. The synthesized compounds 1-8 were evaluated in radioligand binding (A(1), A(2A) and A(3)) and adenylyl cyclase activity (A(2B)) assays in order to determine their affinity for human AR subtypes. The 3-benzamide derivative 4 showed the highest affinity of the whole series and was more than 30-fold selective for the A(3) AR (K-i = 3.24 mu M). The current study supported that small structural changes in this scaffold allowed modulating the affinity resulting in novel promising classes of A(1), A(2A), and/or A(3) AR ligands. We also performed docking calculations in hA(2A) and hA(3) to identify the hypothetical binding mode for the most active compounds. In addition, some ADME properties were calculated in order to better understand the potential of these compounds as drug candidates. (C) 2015 Elsevier Inc. All rights reserved.
• Evaluation of Trypanocidal and Antioxidant Activities of a Selected Series of 3-amidocoumarins
  作者：Mauricio Moncada-Basualto、Michel Lapier、Juan Diego Maya、Betty Matsuhiro、Claudio Olea-Azar、Giovanna L. Delogu、Eugenio Uriarte、Lourdes Santana、Maria Joao Matose

  DOI：10.2174/1573406414666180419113437

  日期：2018.7.12

  Background: Neglected diseases are becoming more prevalent due to globalization. This has inspired active research in the development of new drugs for the treatment of parasitic diseases such as Chagas disease. Objectives: With the aim of finding new trypanocidal agents, we report the in vitro evaluation of a new series of 3-amidocoumarins with or without hydroxyl substituents at position 4 of the coumarin ring. Methods: Electrochemical and biological assays were performed in order to assess the antioxidant and trypanocidal potential of these compounds and to better understand the mechanisms involved in their activity. Results: Most of the studied compounds showed high trypanocidal activity against both epimastigote and trypomastigote forms, with IC50 values in the low micromolar range. Some of them have greater activity and selectivity than the reference compound, nifurtimox. Conclusion: Compound 2 is the most active of this series, being also non-cytotoxic against murine RAW 264.7 macrophages. Electrochemical and radical scavenging experiments were carried out, providing new information about the profile of the best derivatives, and the potential therapeutic application of the new 3-amidocoumarins.

  背景：由于全球化，被忽视的疾病变得越来越普遍。这激发了针对恰加斯病等寄生虫病治疗新药开发的活跃研究。 目的：为了寻找新的杀锥虫剂，我们报告了一系列新型3-酰胺香豆素（有无羟基取代基在香豆素环的4位）的体外评估。 方法：进行了电化学和生物学测试，以评估这些化合物的抗氧化和杀锥虫潜力，并更好地理解其活性涉及的机制。 结果：大多数研究化合物对epimastigote和trypomastigote形式都显示出高度的杀锥虫活性，IC50值在低微摩尔范围内。其中一些化合物比参考化合物硝呋莫司具有更高的活性和选择性。 结论：化合物2是该系列中最活跃的，对小鼠RAW 264.7巨噬细胞也没有细胞毒性。进行了电化学和自由基清除实验，为最佳衍生物的特性提供了新的信息，并展示了新型3-酰胺香豆素的潜在治疗应用。