methyl 5-amino-2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-5-nitro-4-[4-(2-pyridinyl)-1-piperazinyl]benzoate | 1152309-56-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: methyl 5-amino-2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-5-nitro-4-[4-(2-pyridinyl)-1-piperazinyl]benzoate
• 英文别名: methyl 5-amino-2-(3,5-dimethoxy-N-methylanilino)-4-(4-pyridin-2-ylpiperazin-1-yl)benzoate
• CAS: 1152309-56-2
• 化学式: C₂₆H₃₁N₅O₄
• 分子量: 477.563
• InChiKey: IBFIXXJKXCSSQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-amino-2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-5-nitro-4-[4-(2-pyridinyl)-1-piperazinyl]benzoate 在 lithium hydroxide monohydrate 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以11%的产率得到5-amino-2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-4-[4-(2-pyridinyl)-1-piperazinyl]benzoic acid
  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：

  methyl 2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-5-nitro-4-[4-(2-pyridinyl)-1-piperazinyl]benzoate 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45%的产率得到methyl 5-amino-2-[N-(3,5-dimethoxyphenyl)-N-methylamino]-5-nitro-4-[4-(2-pyridinyl)-1-piperazinyl]benzoate
  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

文献信息

• Inhibition of Subgenomic Hepatitis C Virus RNA Replication by Acridone Derivatives: Identification of an NS3 Helicase Inhibitor
  作者：Giuseppe Manfroni、Jan Paeshuyse、Serena Massari、Samantha Zanoli、Barbara Gatto、Giovanni Maga、Oriana Tabarrini、Violetta Cecchetti、Arnaldo Fravolini、Johan Neyts

  DOI：10.1021/jm801608u

  日期：2009.5.28

  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.