7-amino-6-[4-(1,3-benzoxazol-2-yl)-1-piperazinyl]-1-hydroxy-3-methoxy-10-methyl-9(10H)-acridinone | 1152309-17-5

• 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-amino-6-[4-(1,3-benzoxazol-2-yl)-1-piperazinyl]-1-hydroxy-3-methoxy-10-methyl-9(10H)-acridinone
• 英文别名: 7-Amino-6-[4-(1,3-benzoxazol-2-yl)piperazin-1-yl]-1-hydroxy-3-methoxy-10-methyl-acridin-9-one；7-amino-6-[4-(1,3-benzoxazol-2-yl)piperazin-1-yl]-1-hydroxy-3-methoxy-10-methylacridin-9-one
• CAS: 1152309-17-5
• 化学式: C₂₆H₂₅N₅O₄
• 分子量: 471.516
• InChiKey: FYOZEAZUNXOJKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-amino-6-[4-(1,3-benzoxazol-2-yl)-1-piperazinyl]-1,3-dimethoxy-10-methyl-9(10H)-acridinone 在 氢溴酸 、 溶剂黄146 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 8.0h， 以41%的产率得到7-amino-6-[4-(1,3-benzoxazol-2-yl)-1-piperazinyl]-1-hydroxy-3-methoxy-10-methyl-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