1-benzoyl-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione | 670259-07-1

• 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: 1-benzoyl-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione
• 英文别名: 1-benzoyl-3-methyl-2H-naphtho[1,2,3-de]quinoline-2,7(3H)-dione；16-benzoyl-14-methyl-14-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,9(17),10,12-heptaene-8,15-dione
• CAS: 670259-07-1
• 化学式: C₂₄H₁₅NO₃
• 分子量: 365.388
• InChiKey: ZWGSMJQVTOURMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  分散红9 、 苯甲酰乙酸乙酯 在 sodium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 8.0h， 以91%的产率得到1-benzoyl-3-methyl-3H-naphtho[1,2,3-de]quinoline-2,7-dione
  参考文献：
  名称：

  Identification of 3H-Naphtho[1,2,3-de]quinoline-2,7-diones as Inhibitors of Apoptosis Signal-Regulating Kinase 1 (ASK1)

  摘要：

  Apoptosis signal-regulating kinase 1 (ASK1) has recently emerged as an attractive therapeutic target for the treatment of cardiac and neurodegenerative disorders. The selective inhibitors of ASK1 may become important compounds for the development of clinical agents. We have identified the ASK1 inhibitor among 3H-naphtho[1,2,3-de]quinoline-2,7-diones using receptor-based virtual screening. In vitro kinase assay revealed that ethyl 2,7-dioxo-2,7-dihydro-3H-naphtho [1,2,3-de]quinoline-1-carboxylate (NQDI-1) inhibited ASK1 with a K-i of 500 nM. The competitive character of inhibition is demonstrated in Lineweaver-Burk plots. In our preliminary selectivity study this compound exhibited strong specific inhibitory activity toward ASK1.

  DOI：

  10.1021/jm200117h