N-[2-(3-aminopropoxy)-5-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)phenyl]-4-(dimethylamino)butanamide | 1132660-94-6

• 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: N-[2-(3-aminopropoxy)-5-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)phenyl]-4-(dimethylamino)butanamide
• 英文别名: N-[2-(3-aminopropoxy)-5-(5,7-dimethoxy-1-methyl-4-oxo-2-quinolyl)phenyl]-4-(dimethylamino)butanamide；N-[2-(3-aminopropoxy)-5-(5,7-dimethoxy-1-methyl-4-oxoquinolin-2-yl)phenyl]-4-(dimethylamino)butanamide
• CAS: 1132660-94-6
• 化学式: C₂₇H₃₆N₄O₅
• 分子量: 496.607
• InChiKey: ONRXNJPPMRYHRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  t-butyl 3-(4-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)-2-{[4-(dimethylamino)butanoyl]amino}phenoxy)propylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以10%的产率得到N-[2-(3-aminopropoxy)-5-(5,7-dimethoxy-1-methyl-4-oxo-1,4-dihydroquinolin-2-yl)phenyl]-4-(dimethylamino)butanamide
  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

• Synthesis and biological evaluation of 2-phenylquinolones targeted at Tat/TAR recognition
  作者：Giuseppe Manfroni、Barbara Gatto、Oriana Tabarrini、Stefano Sabatini、Violetta Cecchetti、Giulia Giaretta、Cristina Parolin、Claudia Del Vecchio、Arianna Calistri、Manlio Palumbo、Arnaldo Fravolini

  DOI：10.1016/j.bmcl.2008.12.034

  日期：2009.2

  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.