(S)-1-(1,4-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl benzoate | 1239314-56-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: (S)-1-(1,4-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl benzoate
• CAS: 1239314-56-7
• 化学式: C₂₅H₂₄O₆
• 分子量: 420.462
• InChiKey: VDTGGHQMUFTWJN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.89
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-1-(1,4-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl benzoate 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 生成 (S)-1-((5E,8E)-5,8-bis(hydroxyimino)-1,4-dimethoxy-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl benzoate
  参考文献：
  名称：

  Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents

  摘要：

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.

  DOI：

  10.1016/j.bmcl.2014.07.012
• 作为产物：
  描述：

  (S)-4-methyl-1-(1,4,5,8-tetramethoxynaphthalen-2-yl)pent-3-en-1-yl benzoate 在 ammonium cerium (IV) nitrate 作用下， 以 水 为溶剂， 反应 0.25h， 生成 (S)-1-(1,4-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl benzoate
  参考文献：
  名称：

  Synthesis and evaluation of novel alkannin and shikonin oxime derivatives as potent antitumor agents

  摘要：

  A set of forty alkannin and shikonin oxime derivatives were firstly designed and synthesized. Their cytotoxicities against three kinds of tumor cells and a normal cell line were tested and compared with alkannin and shikonin. The cell-based investigation demonstrated that some oxime derivatives were more or comparatively effective to the lead compounds, especially their selective and excellent antitumor activities towards K562 cells with no toxicity in normal cells. We may conclude that oximate modification to the mother nucleus of alkannin and shikonin is an available approach to acquire potent antitumor agents.

  DOI：

  10.1016/j.bmcl.2014.07.012