7-chloro-9-ethyl-6-methoxy-1H,3H,4H,9H-quinolino[2,3-c][1,2]oxazole-3,4-dione | 1082203-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-chloro-9-ethyl-6-methoxy-1H,3H,4H,9H-quinolino[2,3-c][1,2]oxazole-3,4-dione
• 英文别名: 7-chloro-9-ethyl-6-methoxy-1H-[1,2]oxazolo[3,4-b]quinoline-3,4-dione
• CAS: 1082203-90-4
• 化学式: C₁₃H₁₁ClN₂O₄
• 分子量: 294.694
• InChiKey: ICKGZXSYHSVKJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-chloro-9-ethyl-6-methoxy-1H,3H,4H,9H-quinolino[2,3-c][1,2]oxazole-3,4-dione 在 aluminum (III) chloride 作用下， 以 甲苯 为溶剂， 以43%的产率得到7-chloro-9-ethyl-6-hydroxyisoxazolo[3,4-b]quinoline-3,4(1H,9H)-dione
  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：

  在 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 水 为溶剂， 以41%的产率得到7-chloro-9-ethyl-6-methoxy-1H,3H,4H,9H-quinolino[2,3-c][1,2]oxazole-3,4-dione
  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