N,N-dimethyl-2-( (7-hydroxyquinolin-8-yl)-methylene)-hydrazinecarbothioamide | 1537866-15-1

• 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: N,N-dimethyl-2-( (7-hydroxyquinolin-8-yl)-methylene)-hydrazinecarbothioamide
• CAS: 1537866-15-1
• 化学式: C₁₃H₁₄N₄OS
• 分子量: 274.346
• InChiKey: LYEAESRMZPGQFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.75
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  7-hydroxyquinoline-8-carbaldehyde 、 4,4-二甲基-3-氨基硫脲单水合物 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以79%的产率得到N,N-dimethyl-2-( (7-hydroxyquinolin-8-yl)-methylene)-hydrazinecarbothioamide
  参考文献：
  名称：

  Iron Chelators in Photodynamic Therapy Revisited: Synergistic Effect by Novel Highly Active Thiosemicarbazones

  摘要：

  In photodynamic therapy (PDT), a noninvasive anticancer treatment, visible light, is used as a magic bullet selectively destroying cancer cells by a photosensitizer that is nontoxic in the dark. Protoporphyrin IX (PpIX) is a natural photosensitizer synthesized in the cell, which is also a chelating agent that if bonded to Fe2+ forms heme, a central component of hemoglobin. Therefore, xenobiotic iron chelators can disturb iron homeostasis, increasing the accumulation of PpIX, obstructing the last step of heme biosynthesis, and enhancing PDT efficiency. However, the attempts to use this promising idea have not proved to be hugely successful. Herein, we revisited this issue by analyzing the application of iron chelators highly toxic in the dark, which should have higher Fe2+ affinity than the nontoxic chelators used so far. We have designed and prepared thiosemicarbazones (TSC) with the highest dark cellular cytotoxicity among TSCs ever reported. We demonstrate that compound 2 exerts powerful PDT enhancement when used in combination with 5-aminolevulinic acid (ALA), a precursor of PpIX.

  DOI：

  10.1021/ml400422a