Ethyl 3-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxopropanoate | 146447-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Ethyl 3-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxopropanoate
• CAS: 146447-03-2
• 化学式: C₁₂H₁₂ClFO₄
• 分子量: 274.676
• InChiKey: XZFGFPPWZGJQQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  异硫氰酸乙酯 、 Ethyl 3-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxopropanoate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Isoxazolo[3,4-b]quinoline-3,4(1H,9H)-diones as unique, potent and selective inhibitors for Pim-1 and Pim-2 kinases: Chemistry, biological activities, and molecular modeling

  摘要：

  A series of isoxazolo[3,4-b]quinoline-3,4(1H,9H)-diones were synthesized as potent inhibitors against Pim-1 and Pim-2 kinases. The structure-activity-relationship studies started from a high-throughput screening hit and was guided by molecular modeling of inhibitors in the active site of Pim-1 kinase. Installing a hydroxyl group on the benzene ring of the core has the potential to form a key hydrogen bond interaction to the hinge region of the binding pocket and thus resulted in the most potent inhibitor, 19, with K-i values at 2.5 and 43.5 nM against Pim-1 and Pim-2, respectively. Compound 19 also exhibited an activity pro. le with a high degree of kinase selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.079
• 作为产物：
  描述：

  1-(4-Chloro-2-fluoro-5-methoxyphenyl)ethanone 、 碳酸二乙酯 在 sodium hydride 作用下， 生成 Ethyl 3-(4-chloro-2-fluoro-5-methoxyphenyl)-3-oxopropanoate
  参考文献：
  名称：

  Isoxazolo[3,4-b]quinoline-3,4(1H,9H)-diones as unique, potent and selective inhibitors for Pim-1 and Pim-2 kinases: Chemistry, biological activities, and molecular modeling

  摘要：

  A series of isoxazolo[3,4-b]quinoline-3,4(1H,9H)-diones were synthesized as potent inhibitors against Pim-1 and Pim-2 kinases. The structure-activity-relationship studies started from a high-throughput screening hit and was guided by molecular modeling of inhibitors in the active site of Pim-1 kinase. Installing a hydroxyl group on the benzene ring of the core has the potential to form a key hydrogen bond interaction to the hinge region of the binding pocket and thus resulted in the most potent inhibitor, 19, with K-i values at 2.5 and 43.5 nM against Pim-1 and Pim-2, respectively. Compound 19 also exhibited an activity pro. le with a high degree of kinase selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.08.079