6-chloro-N-[3-(dimethylamino)propyl]-5-oxobenzo[a]phenoxazine-11-carboxamide | 1268672-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-chloro-N-[3-(dimethylamino)propyl]-5-oxobenzo[a]phenoxazine-11-carboxamide
• CAS: 1268672-94-1
• 化学式: C₂₂H₂₀ClN₃O₃
• 分子量: 409.872
• InChiKey: ZUFKBDSGYXFYQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-2-氨基苯甲酸 在 1-氯-N,N,2-三甲基丙烯胺 、 potassium acetate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 6-chloro-N-[3-(dimethylamino)propyl]-5-oxobenzo[a]phenoxazine-11-carboxamide
  参考文献：
  名称：

  G-Quadruplex-Binding Benzo[a]phenoxazines Down-Regulate c-KIT Expression in Human Gastric Carcinoma Cells

  摘要：

  There is considerable interest in the structure and function of G-quadruplex nucleic acid secondary structures, their cellular functions, and their potential as therapeutic targets. G-Quadruplex sequence motifs are prevalent in gene pro-moter regions and it has been hypothesized that G-quadruplex structure formation is associated with the transcriptional status of the downstream gene. Using a functional cell-based assay, we have identified two novel G-quadruplex ligands that reduce the transcription of a luciferase reporter driven from the G-quadruplex-containing c-KIT promoter. We have further shown that endogenous c-KIT expression in a human gastric carcinoma cell line is also reduced on treatment with these molecules. Biophysical analysis using surface plasmon resonance has shown that these molecules preferentially bind with high affinity to one of the two G-quadruplex sequences in the c-KIT promoter over double-stranded DNA. This work highlights the utility of cell-based reporter assays to identify new G-quadruplex binding molecules that modulate transcription and identifies benzo[a]phenoxazine derivatives as potential antitumor agents.

  DOI：

  10.1021/ja109474c