N-(3-hydroxypropyl)-2-oxo-2H-chromene-3-carboxamide | 337311-54-3

• 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-(3-hydroxypropyl)-2-oxo-2H-chromene-3-carboxamide
• 英文别名: N-(3-hydroxypropyl)-2-oxochromene-3-carboxamide
• CAS: 337311-54-3
• 化学式: C₁₃H₁₃NO₄
• mdl: MFCD01822293
• 分子量: 247.251
• InChiKey: JUBJBRUNVWXANX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  在 盐酸 、 水 作用下， 生成 N-(3-hydroxypropyl)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships

  摘要：

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.009

文献信息

• A highly selective fluorescent sensor for Fe3+ ion based on coumarin derivatives
  作者：Guo Feng Chen、Hui Ming Jia、Li Yan Zhang、Jing Hu、Bao Hua Chen、Ya Li Song、Ji Tai Li、Guo Yi Bai

  DOI：10.1007/s11164-012-0924-z

  日期：2013.11

  Four amide-containing coumarin derivatives were synthesized. These sensors exhibited a selective fluorescence quenching effect to Fe3+. Among them, sensor 4 shows a pronounced selectivity for Fe3+ over a wide range of tested metal ions in acetonitrile.

  合成了四种含酰胺的香豆素衍生物。这些传感器对Fe3+表现出选择性的荧光淬灭效应。其中，传感器4在宽范围的测试金属离子中对Fe3+表现出明显的选择性，尤其是在乙腈中。
• New chromene scaffolds for adenosine A2A receptors: Synthesis, pharmacology and structure–activity relationships
  作者：Filipe Areias、Marta Costa、Marián Castro、José Brea、Elisabet Gregori-Puigjané、M. Fernanda Proença、Jordi Mestres、María I. Loza

  DOI：10.1016/j.ejmech.2012.05.009

  日期：2012.8

  In silico screening of a c ollection of 1584 academic compounds identified a small molecule hit for the human adenosine A(2A) receptor (pK(i) = 6.2) containing a novel chromene scaffold (3a). To explore the structure activity relationships of this new chemical series for adenosine receptors, a focused library of 43 2H-chromene-3-carboxamide derivatives was synthesized and tested in radioligand binding assays at human adenosine A(1), A(2A), A(2B) and A(3) receptors. The series was found to be enriched with bioactive compounds for adenosine receptors, with 14 molecules showing submicromolar affinity (pK(i) >= 6.0) for at least one adenosine receptor subtype. These results provide evidence that the chromene scaffold, a core structure present in natural products from a wide variety of plants, vegetables, and fruits, constitutes a valuable source for novel therapeutic agents. (C) 2012 Elsevier Masson SAS. All rights reserved.