4-(1-morpholino-1-oxopropan-2-yloxy)-2H-chromen-2-one | 1412905-12-4

• 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: 4-(1-morpholino-1-oxopropan-2-yloxy)-2H-chromen-2-one
• 英文别名: 4-(1-Morpholin-4-yl-1-oxopropan-2-yl)oxychromen-2-one；4-(1-morpholin-4-yl-1-oxopropan-2-yl)oxychromen-2-one
• CAS: 1412905-12-4
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: QQUHEKDMKBLNRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  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 4-(1-morpholino-1-oxopropan-2-yloxy)-2H-chromen-2-one
  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

文献信息

• 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.