2-benzoylpyridine 4,4-diethyl-3-thiosemicarbazone | 168003-30-3

• 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: 2-benzoylpyridine 4,4-diethyl-3-thiosemicarbazone
• 英文别名: 1,1-diethyl-3-[(E)-[phenyl(2-pyridyl)methylene]amino]thiourea；1,1-diethyl-3-[(E)-[phenyl(pyridin-2-yl)methylidene]amino]thiourea
• CAS: 168003-30-3
• 化学式: C₁₇H₂₀N₄S
• 分子量: 312.439
• InChiKey: NGDTWGMNFOZDDX-KNTRCKAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoylpyridine 4,4-diethyl-3-thiosemicarbazone 、 copper dichloride 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Copper(II) complexes of 2-benzoylpyridine 4N-substituted thiosemicarbazones

  摘要：

  2-Benzoylpyridine N-4-substituted thiosemicarbazones commonly coordinate as neutral tridentate ligands to give five coordinate [Cu(HL)Cl-2] complexes when prepared in boiling isopropanol. However, when prepared in boiling ethanol, the anion (loss of the N-3-hydrogen) coordinates as a tridentate ligand to give [CuLCl] complexes. Representative crystal structures of both stoichiometries have been determined. Spectral characterization of both the 2-benzoylpyridine N-4-substituted thiosemicarbazones and their copper(II) complexes includes IR, UV-vis, EPR and NMR studies. Growth inhibition studies of the thiosemicarbazones and their complexes were performed against two human pathogenic fungi.

  DOI：

  10.1016/0277-5387(95)00010-p
• 作为产物：
  描述：

  [[(二乙基氨基)硫代甲酰]硫代]乙酸 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-benzoylpyridine 4,4-diethyl-3-thiosemicarbazone
  参考文献：
  名称：

  Novel Second-Generation Di-2-Pyridylketone Thiosemicarbazones Show Synergism with Standard Chemotherapeutics and Demonstrate Potent Activity against Lung Cancer Xenografts after Oral and Intravenous Administration in Vivo

  摘要：

  We developed a series of second-generation di-2-pyridyl ketone thiosemicarbazone (DpT) and 2-benzoylpyridine thiosemicarbazone (BpT) ligands to improve the efficacy safety profile of these potential antitumor agents. Two novel DpT analogues, Dp4e4mT and DpC, exhibited pronounced and selective activity against human lung cancer xenografts in vivo via the intravenous and oral routes. Importantly, these analogues did not induce the cardiotoxicity observed at high nonoptimal doses of the first-generation DpT analogue, Dp44mT. The Cu(II) complexes of these ligands exhibited potent antiproliferative activity having redox potentials in a range accessible to biological reductants. The activity of the copper complexes of Dp4e4mT and DpC against lung cancer cells was synergistic in combination with gemcitabine or cisplatin. It was demonstrated by EPR spectroscopy that dimeric copper compounds of the type [CuLCl](2), identified crystallographically, dissociate in solution to give monomeric 1:1 Cu:ligand complexes. These monomers represent the biologically active form of the complex.

  DOI：

  10.1021/jm300768u

文献信息

• Anti-cancer and anti-angiogenic activities of some synthetic Ni(II) thiosemicarbazone complexes
  作者：Chinmoy Biswas、Vinu Vijayan、Subhra Jyoti Panda、Chandra Shekhar Purohit、Manikantan Syamala Kiran、Rajarshi Ghosh

  DOI：10.1016/j.poly.2024.116888

  日期：2024.4

  Three Ni(II) complexes of thiosemicarbazone, two mononuclear and one dinuclear, has been synthesized and X-ray crystallographically characterized. Each of the metal centers in and are found to have square planar geometries. adopts octahedral geometry at its Ni(II) center. All the complexes show anti-cancer and anti-angiogenic activities. According to Chorio-Allantoic Membrane (CAM) assay, all the Ni(II)

  合成了三种缩氨基硫脲 Ni(II) 配合物（两种单核和一种双核）并进行了 X 射线晶体学表征。发现每个金属中心都具有正方形平面几何形状。Ni(II) 中心采用八面体几何形状。所有复合物均显示出抗癌和抗血管生成活性。根据绒毛尿囊膜 (CAM) 测定，所有 Ni(II) 复合物均被发现在 24 小时内分别促进毛细血管生长 18.18%、-10.7% 和 –22.7%。在主动脉弓测定中，复合物显示样品对主动脉组成细胞（即内皮细胞、成纤维细胞和平滑肌细胞）的增殖和迁移的抑制作用。
• Novel Second-Generation Di-2-Pyridylketone Thiosemicarbazones Show Synergism with Standard Chemotherapeutics and Demonstrate Potent Activity against Lung Cancer Xenografts after Oral and Intravenous Administration in Vivo
  作者：David B. Lovejoy、Danae M. Sharp、Nicole Seebacher、Peyman Obeidy、Thomas Prichard、Christian Stefani、Maram T. Basha、Philip C. Sharpe、Patric J. Jansson、Danuta S. Kalinowski、Paul V. Bernhardt、Des R. Richardson

  DOI：10.1021/jm300768u

  日期：2012.8.23

  We developed a series of second-generation di-2-pyridyl ketone thiosemicarbazone (DpT) and 2-benzoylpyridine thiosemicarbazone (BpT) ligands to improve the efficacy safety profile of these potential antitumor agents. Two novel DpT analogues, Dp4e4mT and DpC, exhibited pronounced and selective activity against human lung cancer xenografts in vivo via the intravenous and oral routes. Importantly, these analogues did not induce the cardiotoxicity observed at high nonoptimal doses of the first-generation DpT analogue, Dp44mT. The Cu(II) complexes of these ligands exhibited potent antiproliferative activity having redox potentials in a range accessible to biological reductants. The activity of the copper complexes of Dp4e4mT and DpC against lung cancer cells was synergistic in combination with gemcitabine or cisplatin. It was demonstrated by EPR spectroscopy that dimeric copper compounds of the type [CuLCl](2), identified crystallographically, dissociate in solution to give monomeric 1:1 Cu:ligand complexes. These monomers represent the biologically active form of the complex.
• Copper(II) complexes of 2-benzoylpyridine 4N-substituted thiosemicarbazones
  作者：Douglas X. West、Janeice S. Ives、Jacqueline Krejci、Michelle M. Salberg、Terri L. Zumbahlen、Gordon A. Bain、Anthony E. Liberta、Jesus Valdes-Martinez、Simon Hernandez-Ortiz、Ruben A. Toscano

  DOI：10.1016/0277-5387(95)00010-p

  日期：1995.8

  2-Benzoylpyridine N-4-substituted thiosemicarbazones commonly coordinate as neutral tridentate ligands to give five coordinate [Cu(HL)Cl-2] complexes when prepared in boiling isopropanol. However, when prepared in boiling ethanol, the anion (loss of the N-3-hydrogen) coordinates as a tridentate ligand to give [CuLCl] complexes. Representative crystal structures of both stoichiometries have been determined. Spectral characterization of both the 2-benzoylpyridine N-4-substituted thiosemicarbazones and their copper(II) complexes includes IR, UV-vis, EPR and NMR studies. Growth inhibition studies of the thiosemicarbazones and their complexes were performed against two human pathogenic fungi.