1-(5-fluoro-2-nitrophenyl)-4-(2-pyridinyl)piperazine | 1152309-57-3

• 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: 1-(5-fluoro-2-nitrophenyl)-4-(2-pyridinyl)piperazine
• 英文别名: 1-(5-Fluoro-2-nitrophenyl)-4-pyridin-2-ylpiperazine
• CAS: 1152309-57-3
• 化学式: C₁₅H₁₅FN₄O₂
• 分子量: 302.308
• InChiKey: CITARAWENUTXBO-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  495.0±45.0 °C(predicted)
• 密度：
  1.336±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(5-fluoro-2-nitrophenyl)-4-(2-pyridinyl)piperazine 、 3,5-dimethoxy-N-methylaniline 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 以56%的产率得到N-(3,5-dimethoxyphenyl)-N-methyl-4-nitro-3-[4-(2-pyridinyl)-1-piperazinyl]aniline
  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-(2-吡啶基)哌嗪 、 2,4-二氟硝基苯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以58%的产率得到1-(5-fluoro-2-nitrophenyl)-4-(2-pyridinyl)piperazine
  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.