ethyl 2-[(2-oxo-2H-chromen-4-yl)oxy]propanoate | 312929-05-8

• 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: ethyl 2-[(2-oxo-2H-chromen-4-yl)oxy]propanoate
• 英文别名: Ethyl 2-(2-oxochromen-4-yl)oxypropanoate
• CAS: 312929-05-8
• 化学式: C₁₄H₁₄O₅
• 分子量: 262.262
• InChiKey: VUVAYYSXHCBGGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(2-oxo-2H-chromen-4-yl)oxy]propanoate 在 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2-oxo-2H-chromen-4-yloxy)-N-(pyridin-4-yl)propanamide
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors

  摘要：

  A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy) propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.082
• 作为产物：
  描述：

  4-羟基香豆素 、 2-溴丙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 ethyl 2-[(2-oxo-2H-chromen-4-yl)oxy]propanoate
  参考文献：
  名称：

  N-[(吲哚基)乙基)香豆素-基氧基)]链烷酰胺的合成及抗乙酰胆碱酯酶活性

  摘要：

  合成了通过接头连接的新型香豆素-色胺系统，并通过经典的 Ellman 测试在体外针对乙酰胆碱酯酶进行了评估。

  DOI：

  10.3184/174751917x14859570937677

文献信息

• Synthesis and Anti-Acetylcholinesterase Activity of N-[(indolyl)ethyl)-coumarin-yloxy)]Alkanamides
  作者：Sarah Ghanei-Nasab、Hamid Nadri、Alireza Moradi、Azam Marjani、Shabnam Shabani、Loghman Firoozpour、Setareh Moghimi、Mehdi Khoobi、Farzin Hadizadeh、Alireza Foroumadi

  DOI：10.3184/174751917x14859570937677

  日期：2017.2

  Novel coumarin–tryptamine systems attached through a linker were synthesised and evaluated in vitro against acetylcholinesterase by the classical Ellman's test.

  合成了通过接头连接的新型香豆素-色胺系统，并通过经典的 Ellman 测试在体外针对乙酰胆碱酯酶进行了评估。
• Synthesis and pharmacological evaluation of N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide as cyclooxygenase inhibitors
  作者：D. Rambabu、Naveen Mulakayala、Ismail、K. Ravi Kumar、G. Pavan Kumar、Chaitanya Mulakayala、Chitta Suresh Kumar、Arunasree M. Kalle、M.V. Basaveswara Rao、Srinivas Oruganti、Manojit Pal

  DOI：10.1016/j.bmcl.2012.08.082

  日期：2012.11

  A series of novel N-substituted 2-(2-oxo-2H-chromen-4-yloxy)propanamide derivatives were synthesized via converting the readily available 4-hydroxy coumarin to the corresponding ethyl 2-(2-oxo-2H-chromen-4-yloxy) propanoate followed by hydrolysis and then reacting with different substituted amines. The molecular structures of two representative compounds, that is, 3 and 5l were confirmed by single crystal X-ray diffraction study. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. The compound 5i showed balanced selectivity towards COX-2 over COX-1 inhibition and good docking scores when docked into the COX-2 protein. (C) 2012 Elsevier Ltd. All rights reserved.