2-(4-chloro-3-nitrophenyl)-5,7-dimethoxy-1-methylquinolin-4(1H)-one | 1132660-81-1

• 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: 2-(4-chloro-3-nitrophenyl)-5,7-dimethoxy-1-methylquinolin-4(1H)-one
• CAS: 1132660-81-1
• 化学式: C₁₈H₁₅ClN₂O₅
• 分子量: 374.78
• InChiKey: OBOGZWUSJQARSM-UHFFFAOYSA-N

物化性质

• 熔点：
  240-241 °C(Solv: dimethyl sulfoxide (67-68-5))
• 沸点：
  582.8±50.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  83.6
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-3-nitrophenyl)-5,7-dimethoxy-1-methylquinolin-4(1H)-one 在 氢氧化钾 、 水 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以80%的产率得到2-(4-hydroxy-3-nitrophenyl)-5,7-dimethoxy-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-phenylquinolones targeted at Tat/TAR recognition

  摘要：

  Tat (transactivator of transcription) is a small HIV protein rich in arginines that interacts with a viral RNA structure called TAR (trans-activation responsive region). Tat-TAR interaction is essential for viral gene expression, replication and pathogenesis. Small molecules able to interfere with TAR and to compete for Tat binding possess antiviral activity due to inhibition of viral transcription and expression, thus impairing formation of infectious virions. We report here, the synthesis and biological evaluation of a new series of quinolone derivatives, namely 2-phenylquinolones, designed with the aim of interfering with the protein/RNA complex. These new derivatives are able to efficiently interfere with Tat/TAR complex in vitro depending on precise structural requirements as demonstrated by fluorescence quenching assay analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.034
• 作为产物：
  描述：

  N-(2-acetyl-3,5-dimethoxyphenyl)-4-chloro-N-methyl-3-nitrobenzamide 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以74%的产率得到2-(4-chloro-3-nitrophenyl)-5,7-dimethoxy-1-methylquinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-phenylquinolones targeted at Tat/TAR recognition

  摘要：

  Tat (transactivator of transcription) is a small HIV protein rich in arginines that interacts with a viral RNA structure called TAR (trans-activation responsive region). Tat-TAR interaction is essential for viral gene expression, replication and pathogenesis. Small molecules able to interfere with TAR and to compete for Tat binding possess antiviral activity due to inhibition of viral transcription and expression, thus impairing formation of infectious virions. We report here, the synthesis and biological evaluation of a new series of quinolone derivatives, namely 2-phenylquinolones, designed with the aim of interfering with the protein/RNA complex. These new derivatives are able to efficiently interfere with Tat/TAR complex in vitro depending on precise structural requirements as demonstrated by fluorescence quenching assay analysis. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.034

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.