(E)-N-phenyl-2-(pyridin-4-ylmethylene)hydrazine-1-carbothioamide | 67526-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-N-phenyl-2-(pyridin-4-ylmethylene)hydrazine-1-carbothioamide
• 英文别名: pyridine-4-carbaldehyde-(4-phenyl thiosemicarbazone)；Pyridin-4-carbaldehyd-(4-phenyl-thiosemicarbazon)；1-phenyl-3-[(E)-pyridin-4-ylmethylideneamino]thiourea
• CAS: 67526-44-7
• 化学式: C₁₃H₁₂N₄S
• 分子量: 256.331
• InChiKey: QCORIWKQACWACT-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫代异氰酸苯酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (E)-N-phenyl-2-(pyridin-4-ylmethylene)hydrazine-1-carbothioamide
  参考文献：
  名称：

  Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

  摘要：

  In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 mu M, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial-mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112349

文献信息

• Grammaticakis, Bulletin de la Societe Chimique de France, 1956, p. 109,115
  作者：Grammaticakis

  DOI：——

  日期：——