N-(3-chloro-2-methylphenyl)-2-(2-oxo-2H-chromen-4-yloxy)propanamide | 1412905-06-6

• 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-chloro-2-methylphenyl)-2-(2-oxo-2H-chromen-4-yloxy)propanamide
• 英文别名: N-(3-chloro-2-methylphenyl)-2-(2-oxochromen-4-yl)oxypropanamide
• CAS: 1412905-06-6
• 化学式: C₁₉H₁₆ClNO₄
• 分子量: 357.793
• InChiKey: GROHBJLESHZNGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 在 potassium carbonate 、 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 、 丙酮 为溶剂， 反应 7.0h， 生成 N-(3-chloro-2-methylphenyl)-2-(2-oxo-2H-chromen-4-yloxy)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

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.