(E)-2-(4-(bis(2-hydroxyethyl)amino)benzylidene)hydrazinecarbothioamide | 88615-44-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-2-(4-(bis(2-hydroxyethyl)amino)benzylidene)hydrazinecarbothioamide
• 英文别名: 4-[bis-(2-hydroxy-ethyl)-amino]-benzaldehyde-thiosemicarbazone；4-[Bis-(2-hydroxy-aethyl)-amino]-benzaldehyd-thiosemicarbazon
• CAS: 88615-44-5
• 化学式: C₁₂H₁₈N₄O₂S
• 分子量: 282.367
• InChiKey: VZHRYQQPWWHDKD-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.11
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-[N,N-双(2-羟乙基)氨基]苯甲醛 、 氨基硫脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以64%的产率得到(E)-2-(4-(bis(2-hydroxyethyl)amino)benzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Syntheses, quantum mechanical modeling, biomolecular interaction and in vitro anticancer – Tubulin activity of thiosemicarbazones

  摘要：

  A new series of thiosemicarbazones were designed and synthesized. Their structures were confirmed by spectral characterization and single crystal XRD studies. Compounds MTSC-2 and ETSC-3 crystallized in the orthorhombic crystal system with space group Pbc2(1) and Pca2(1) respectively. Density functional theory computational studies were performed on MTSC-2 and ETSC-3 along with natural bond orbital analysis and Mulliken population analysis to study the structural and electronic properties of the thiosemicarbazones. The HOMOs of the two thiosemicarbazones are - 5.2943 and - 5.1133 eV respectively while the LUMO5 are - 1.6879 and - 1.6398 eV respectively. The energy gap is 3.6064 and 3.4736 eV respectively. Molecular docking studies were performed to determine the binding mode of the thiosemicarbazones against beta-tubulin. The theoretical studies were further supplemented with tubulin polymerization inhibition assay. All the four thiosemicarbazones proved effective in inhibiting the polymerization of alpha- and beta-tubulin heterodimers into microtubules. The anticancer activity of these compounds showed their extreme potency against A549 and HepG2 cancer cell lines with IC50, values of 0.051 - 0.189 mu m and 0.042 - 0.136 mu m respectively. Compound PTSC-4 showed the highest activity both against tubulin and the two cancer cell lines. This was in correlation with the theoretical studies. Hence, these four compounds, specifically PTSC-4, can be considered to be potential leads in the development of nonmetallic anticancer agents.

  DOI：

  10.1016/j.bioorg.2020.104081