ethyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzoate | 1068575-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzoate
• CAS: 1068575-23-4
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: TWEVDNMURIVVML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.53
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzoate 在 N-甲基吗啉 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 potassium trimethylsilonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 3-[3-bromo-4-[(2,4-difluorobenzyl)oxy]-6-methyl-2-oxopyridin-1(2H)-yl]benzamide
  参考文献：
  名称：

  Design, synthesis and activity of a potent, selective series of N -aryl pyridinone inhibitors of p38 kinase

  摘要：

  A series of N-aryl pyridinone inhibitors of p38 mitogen activated protein (MAP) kinase were designed and prepared based on the screening hit SC-25028 (1) and structural comparisons to VX-745 (5). The focus of the investigation targeted the dependence of potency and metabolic stability on the benzyloxy connectivity, the role of the C-6 position and the substitution pattern on the N-phenyl ring. Further optimization produced the highly selective and potent pyridinones 2 and 3. These inhibitors exhibited activity in both acute and chronic models of inflammation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.120
• 作为产物：
  描述：

  3-氨基苯甲酸乙酯 、 4-羟基-6-甲基-2-吡喃酮 以 邻二氯苯 为溶剂， 反应 0.25h， 以37%的产率得到ethyl 3-(4-hydroxy-6-methyl-2-oxopyridin-1(2H)-yl)benzoate
  参考文献：
  名称：

  Design, synthesis and activity of a potent, selective series of N -aryl pyridinone inhibitors of p38 kinase

  摘要：

  A series of N-aryl pyridinone inhibitors of p38 mitogen activated protein (MAP) kinase were designed and prepared based on the screening hit SC-25028 (1) and structural comparisons to VX-745 (5). The focus of the investigation targeted the dependence of potency and metabolic stability on the benzyloxy connectivity, the role of the C-6 position and the substitution pattern on the N-phenyl ring. Further optimization produced the highly selective and potent pyridinones 2 and 3. These inhibitors exhibited activity in both acute and chronic models of inflammation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.120