2-(benzo[d]thiazol-2-ylmethylene)-N,N-dimethylhydrazinecarbothioamide | 1035163-12-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-ylmethylene)-N,N-dimethylhydrazinecarbothioamide
• 英文别名: 3-(1,3-benzothiazol-2-ylmethylideneamino)-1,1-dimethylthiourea
• CAS: 1035163-12-2
• 化学式: C₁₁H₁₂N₄S₂
• 分子量: 264.375
• InChiKey: ABPSNKQSKCJNIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.52
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯并噻唑-2-甲醛 、 4,4-二甲基-3-氨基硫脲单水合物 以 异丙醇 为溶剂， 反应 0.42h， 以87%的产率得到2-(benzo[d]thiazol-2-ylmethylene)-N,N-dimethylhydrazinecarbothioamide
  参考文献：
  名称：

  A Series of α-Heterocyclic Carboxaldehyde Thiosemicarbazones Inhibit Topoisomerase IIα Catalytic Activity

  摘要：

  A series of novel thiosemicarbazone derivatives bearing condensed heterocyclic carboxaldehyde moieties were designed and synthesized. Among them, TSC24 exhibited broad antiproliferative activity in a panel of human tumor cells and suppressed tumor growth in mice. The mechanism research revealed that TSC24 was not only an iron chelator but also a topoisomerase II alpha catalytic inhibitor. Its inhibition on topoisomerase II alpha was due to direct interaction with the ATPase domain of topoisomerase I la which led to the block of ATP hydrolysis. Molecular docking predicted that TSC24 might bind at the ATP binding site, which was confirmed by the competitive inhibition assay. These results about the mechanisms involved in the anticancer activities of thiosemicarbazones will aid in the rational design of novel topoisomerase II-targeted drugs and will provide insights into the discovery and development of novel cancer therapeutics based on the dual activity to chelate iron and to inhibit the catalytic activity of topoisomerase II alpha.

  DOI：

  10.1021/jm9014394