1-isobutoxy-3-methoxy-10-methyl-7-nitro-6-[4-(2-pyridinyl)-1-piperazinyl]-9(10H)-acridinone | 1152309-51-7

• 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-isobutoxy-3-methoxy-10-methyl-7-nitro-6-[4-(2-pyridinyl)-1-piperazinyl]-9(10H)-acridinone
• 英文别名: 3-Methoxy-10-methyl-1-(2-methylpropoxy)-7-nitro-6-(4-pyridin-2-ylpiperazin-1-yl)acridin-9-one
• CAS: 1152309-51-7
• 化学式: C₂₈H₃₁N₅O₅
• 分子量: 517.585
• InChiKey: AZAKAJKRKVBAFY-UHFFFAOYSA-N

物化性质

• 熔点：
  294-296 °C
• 沸点：
  735.2±60.0 °C(predicted)
• 密度：
  1.280±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-isobutoxy-3-methoxy-10-methyl-7-nitro-6-[4-(2-pyridinyl)-1-piperazinyl]-9(10H)-acridinone 在 氢气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 以32%的产率得到7-amino-1-isobutoxy-3-methoxy-10-methyl-6-[4-(2-pyridynyl)-1-piperazinyl]-9(10H)-acridinone
  参考文献：
  名称：

  Inhibition of Subgenomic Hepatitis C Virus RNA Replication by Acridone Derivatives: Identification of an NS3 Helicase Inhibitor

  摘要：

  We report the synthesis and structure - activity relationship (SAR) of a large series of acridones and acridone-fragment derivatives designed on the basis of the selective antihepatitis C virus (HCV) activity shown by acridone 2, previously studied as a potential antibovine viral diarrhea virus (BVDV) compound. The evaluation of their ability to inhibit the HCV replication in Huh-5-2 cells led to the identification of new, selective inhibitors. This indicates that the acridone skeleton, when properly functionalized, is a suitable scaffold to obtain potential anti-HCV agents. Interestingly, during identification of possible cellular and viral targets, it was discovered that compound 23 exerts inhibitory activity on the HCV NS3 helicase, a very promising target for the development of anti-HCV drugs.

  DOI：

  10.1021/jm801608u
• 作为产物：
  描述：

  1-hydroxy-3-methoxy-10-methyl-7-nitro-6-[4-(2-pyridinyl)-1-piperazinyl]-9(10H)-acridinone 、 碘代异丁烷 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以45%的产率得到1-isobutoxy-3-methoxy-10-methyl-7-nitro-6-[4-(2-pyridinyl)-1-piperazinyl]-9(10H)-acridinone
  参考文献：
  名称：

  Inhibition of Subgenomic Hepatitis C Virus RNA Replication by Acridone Derivatives: Identification of an NS3 Helicase Inhibitor

  摘要：

  We report the synthesis and structure - activity relationship (SAR) of a large series of acridones and acridone-fragment derivatives designed on the basis of the selective antihepatitis C virus (HCV) activity shown by acridone 2, previously studied as a potential antibovine viral diarrhea virus (BVDV) compound. The evaluation of their ability to inhibit the HCV replication in Huh-5-2 cells led to the identification of new, selective inhibitors. This indicates that the acridone skeleton, when properly functionalized, is a suitable scaffold to obtain potential anti-HCV agents. Interestingly, during identification of possible cellular and viral targets, it was discovered that compound 23 exerts inhibitory activity on the HCV NS3 helicase, a very promising target for the development of anti-HCV drugs.

  DOI：

  10.1021/jm801608u