(E)-2-((1H-indol-3-yl)methylene)-N-phenylhydrazine-1-carbothioamide | 7274-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-2-((1H-indol-3-yl)methylene)-N-phenylhydrazine-1-carbothioamide
• 英文别名: 2-((1H-Indol-3-yl)methylene)-N-phenylhydrazinecarbothioamide；1-[(E)-1H-indol-3-ylmethylideneamino]-3-phenylthiourea
• CAS: 7274-93-3
• 化学式: C₁₆H₁₄N₄S
• 分子量: 294.38
• InChiKey: FMUWNGSZLDHRAS-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (E)-2-((1H-indol-3-yl)methylene)-N-phenylhydrazine-1-carbothioamide 以 甲醇 为溶剂， 反应 1.17h， 以79%的产率得到
  参考文献：
  名称：

  Synthesis, cytotoxicity and docking studies (with SARS-CoV-2) of water-soluble binuclear Ru-p-cymene complex holding indole thiosemicarbazone ligand

  摘要：

  DOI：

  10.1016/j.inoche.2021.109029
• 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)-2-((1H-indol-3-yl)methylene)-N-phenylhydrazine-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

• Synthesis of Ni(II) complexes bearing indole-based thiosemicarbazone ligands for interaction with biomolecules and some biological applications
  作者：Jebiti Haribabu、Kumaramangalam Jeyalakshmi、Yuvaraj Arun、Nattamai S. P. Bhuvanesh、Paramasivan Thirumalai Perumal、Ramasamy Karvembu

  DOI：10.1007/s00775-016-1424-1

  日期：2017.6

  A series of new Ni(II) complexes containing indole-based thiosemicarbazone ligands was synthesized and characterized by elemental analyses, and UV-visible, FT-IR, 1H & 13C NMR and mass spectroscopic techniques. The Ni(II) complexes (1-4) bear the general formula [NiC10H9N2NHCSNH(R)}2] where R = hydrogen (1), 4-methyl (2), 4-phenyl (3) and 4-cyclohexyl (4). Molecular structure of ligands (L3 and L4)

  合成了一系列含有吲哚基硫代半碳酰胺配体的新型Ni（II）配合物，并通过元素分析，紫外可见，FT-IR，1H和13C NMR和质谱技术对其进行了表征。Ni（II）配合物（1-4）具有通式[Ni C10H9N2NHCSNH（R）} 2]，其中R =氢（1），4-甲基（2），4-苯基（3）和4-环己基（4）。配体（L3和L4）和配合物（2、3和4）的分子结构通过单晶X射线晶体学证实。四个配位的Ni（II）配合物显示出正方形的平面几何形状。Ni（II）配合物与小牛胸腺DNA（CT-DNA）的相互作用已通过吸收光谱法和溴化乙锭（EB）竞争结合研究进行了评估，该研究揭示了配合物与CT-DNA的嵌入相互作用。凝胶电泳实验表明，复合物可切割DNA，而无需任何外部试剂。此外，使用紫外可见，荧光和同步荧光光谱方法研究了该复合物与牛血清白蛋白（BSA）的相互作用，这表明该复合物可以与BSA牢固结合。分子对接用
• Effect of N-benzyl group in indole scaffold of thiosemicarbazones on the biological activity of their Pd(II) complexes: DFT, biomolecular interactions, in silico docking, ADME and cytotoxicity studies
  作者：Nithya Balakrishnan、Jebiti Haribabu、Rahime Eshaghi Malekshah、Srividya Swaminathan、Chandrasekar Balachandran、Nattamai Bhuvanesh、Shin Aoki、Ramasamy Karvembu

  DOI：10.1016/j.ica.2022.120805

  日期：2022.5

  cisplatin. Beneficially, the active complex showed less toxicity against IMR-90 normal cells. Further, the results of AO-EB staining studies indicated that the complexes induced cell death via apoptosis pathway. The steric influence of the substituted indole moiety, its limited electronic effects and lesser stability in aqueous systems retarded the Pd(II) complexes of N-benzyl substituted indole TSCs

  一系列N-苄基取代的吲哚基氨基硫脲 (TSC) 配体 (L4-L6) 和钯 (II) TSC 配合物 [Pd(L) 2 ] ( 1 - 6 ) (L = 单阴离子双齿未/ N-取代基于吲哚的 TSC 配体）已使用分析和光谱工具合成和表征。L4- L6和配合物(2-4和6)的确切分子结构通过单晶X射线衍射(XRD)方法确定。光谱和晶体学研究表明，Pd(II) 离子与 TSC 作为一元双齿配体配位，形成两个具有方形平面几何形状的五元环。N的影响采用DFT方法研究了配合物中TSCs吲哚支架中的-苄基取代，并探讨了构效关系（SAR）。就其亲脂性和口服生物利用度而言，彻底分析了配体及其复合物的计算机ADME 特性。配合物 ( 1 - 6) 表现出与小牛胸腺 DNA (CT DNA) 的强烈嵌入，通过吸收/发射光谱滴定和粘度测量对其进行了检查。类似地，牛血清白蛋白 (BSA) 与使用光谱方法检查的复合
• Identification of (E)-1-((1H-indol-3-yl)methylene)-4-substitute-thiosemicarbazones as potential anti-hepatic fibrosis agents
  作者：Gang Lin、Yijing Zhong、Shengwei Hu、Fengming He、Zhaolin Zhang、Weibi Li、Hongyu Hu、Jin-Zhang Zeng

  DOI：10.1016/j.bioorg.2023.107022

  日期：2024.2