bis(4-ethyl-3-thiosemicarbazone)-2,6-diacetylpyridine | 908080-16-0

• 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: bis(4-ethyl-3-thiosemicarbazone)-2,6-diacetylpyridine
• 英文别名: bis(4-N-ethylthiosemicarbazone)-2,6-diacetylpyridine；2,6-diacetylpyridine bis(4-ethylthiosemicarbazone)；2,6-Diacetylpyridine bis(n4-ethylthiosemicarbazone)；1-ethyl-3-[1-[6-[N-(ethylcarbamothioylamino)-C-methylcarbonimidoyl]pyridin-2-yl]ethylideneamino]thiourea
• CAS: 908080-16-0
• 化学式: C₁₅H₂₃N₇S₂
• 分子量: 365.527
• InChiKey: ZINONERQPCFXDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  150
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(4-ethyl-3-thiosemicarbazone)-2,6-diacetylpyridine 以 甲醇 、 氘代二甲亚砜 为溶剂， 生成 [Cd(bis(4-N-ethylthiosemicarbazone)-2,6-diacetylpyridine^(2-))]2*DMSO-d6
  参考文献：
  名称：

  Pentadentate thiosemicarbazones as versatile chelating systems. A comparative structural study of their metallic complexes

  摘要：

  我们采用化学和电化学方法，制备了一些过渡金属和后过渡金属配合物，这些配合物来自五齿硫代氨基甲酰肼配体双（4-N-乙基硫代氨基甲酰肼）-2,6-二乙酰基吡啶 H2LEt。这些配合物已经合成并完全表征，包括配体 H2LEt 及其锰、镉和铅配合物的晶体结构。我们还分别对银、镉、锡和铅化合物进行了多核 109Ag、113Cd、119Sn 和 207Pb 研究。此外，我们在此对五齿硫代氨基甲酰肼配合物的不同结构进行了比较研究，试图检查不同因素（如实验程序、金属大小、配体结构和金属氧化态）对所形成配合物的最终结构的影响。我们的目标是更好地了解五齿硫代氨基甲酰肼配体的配位趋势。

  DOI：

  10.1039/b810601k
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 、 4-乙基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 bis(4-ethyl-3-thiosemicarbazone)-2,6-diacetylpyridine
  参考文献：
  名称：

  Cytotoxic activity of expanded coordination bis-thiosemicarbazones and copper complexes thereof

  摘要：

  A series of bis-thiosemicarbazone agents with coordinating groups capable of multiple metal coordination modes has been generated and evaluated for potential cytotoxic effects against melanoma (MelRm) and breast adenocarcinoma (MCF-7) cell lines. The bis-thiosemicarbazones in this study generally demonstrated superior cytotoxic activity against MelRm than MCF-7 in the absence of metal ion supplementation, but in most cases could not be considered superior to the reference thiosemicarbazone Dp44mT. The key structural features for the cytotoxic activity were the central metal binding atom on the aromatic core, the thiocarbonyl residue and the nature of substitution on the N4-terminus in terms of size and lipophilicity. The cytotoxicity of bis-thiosemicarbazone ligands improved significantly with Cu(II) supplementation, particularly against MCF-7 cells. The mechanism of cytotoxicity of bis-thiosemicarbazones was proposed to be dependent on the combined effect of metal mobilisation and ROS generation which is so called a "double-punch effect".

  DOI：

  10.1007/s00775-016-1390-7

文献信息

• Synthesis and spectral investigations of Mn(II) complexes of pentadentate bis(thiosemicarbazones)
  作者：Suja Krishnan、K. Laly、M.R. Prathapachandra Kurup

  DOI：10.1016/j.saa.2009.11.022

  日期：2010.2

  molecules and coordinate to Mn(II) ion through two thione sulfur atoms, two azomethine nitrogens and the pyridine nitrogen, suggesting a heptacoordination. While in compound [Mn(Ac4Ph)H2O], the dianionic ligand is coordinated to the metal suggesting six coordination in this case. Magnetic studies indicate the high spin state of Mn(II). Conductivity measurements reveal their non-electrolyte nature. EPR

  双（硫代半氨基甲酮）的五种Mn（II）络合物，分别表示为[Mn（H 2 Ac4Ph）Cl 2 ]（1），[Mn（Ac4Ph）H 2 O]（2），[Mn（H 2 Ac4Cy）Cl合成了2 ]·H 2 O（3），[Mn（H 2 Ac4Et）Cl 2 ]·3H 2 O（4）和[Mn（H 2 Ac4Et）（OAc）2 ]·3H 2 O（5）并具有元素分析，电子，红外和EPR光谱技术的特点。除[Mn（Ac4Ph）H 2以外的所有配合物O]，配体充当五齿中性分子，并通过两个硫酮硫原子，两个偶氮甲碱氮原子和吡啶氮原子与Mn（II）离子配位，表明存在七配位。而在化合物[Mn（Ac4Ph）H 2 O]中，双阴离子配体与金属配位，表明在这种情况下为六价配位。磁性研究表明Mn（II）的高自旋态。电导率测量显示其非电解质性质。EPR研究表明[Mn（Ac4Ph）H 2 O]的5 g值显示零场分裂。
• Route to Cluster Helicates
  作者：Manuel R. Bermejo、Ana M. González-Noya、Rosa M. Pedrido、María J. Romero、Miguel Vázquez

  DOI：10.1002/anie.200500840

  日期：2005.7.4
• Pentadentate thiosemicarbazones as versatile chelating systems. A comparative structural study of their metallic complexes
  作者：Rosa Pedrido、Ana M. González-Noya、Maria J. Romero、Miguel Martínez-Calvo、Miguel Vázquez López、Esther Gómez-Fórneas、Guillermo Zaragoza、Manuel R. Bermejo

  DOI：10.1039/b810601k

  日期：——

  We have prepared some transition and post-transition metal complexes derived from the pentadentate thiosemicarbazone ligand bis(4-N-ethylthiosemicarbazone)-2,6-diacetylpyridine H2LEt, by both chemical and electrochemical procedures. The complexes have been synthesised and fully characterised, including the crystal structures for the ligand H2LEt and its manganese, cadmium and lead complexes. We have also performed multinuclear 109Ag, 113Cd, 119Sn and 207Pb studies for silver, cadmium, tin and lead compounds, respectively. Moreover we present here a comparative study on the different structures found for pentadentate thiosemicarbazonate complexes, trying to check the influence of different factors, such as experimental procedure, size of metal, structure of the ligand, and metal oxidation state, on the final structure of the complex formed. Our aim is gaining a better insight into the coordination trends of pentadentate thiosemicarbazone ligands.

  我们采用化学和电化学方法，制备了一些过渡金属和后过渡金属配合物，这些配合物来自五齿硫代氨基甲酰肼配体双（4-N-乙基硫代氨基甲酰肼）-2,6-二乙酰基吡啶 H2LEt。这些配合物已经合成并完全表征，包括配体 H2LEt 及其锰、镉和铅配合物的晶体结构。我们还分别对银、镉、锡和铅化合物进行了多核 109Ag、113Cd、119Sn 和 207Pb 研究。此外，我们在此对五齿硫代氨基甲酰肼配合物的不同结构进行了比较研究，试图检查不同因素（如实验程序、金属大小、配体结构和金属氧化态）对所形成配合物的最终结构的影响。我们的目标是更好地了解五齿硫代氨基甲酰肼配体的配位趋势。
• Cytotoxic activity of expanded coordination bis-thiosemicarbazones and copper complexes thereof
  作者：Fady N. Akladios、Scott D. Andrew、Christopher J. Parkinson

  DOI：10.1007/s00775-016-1390-7

  日期：2016.12

  A series of bis-thiosemicarbazone agents with coordinating groups capable of multiple metal coordination modes has been generated and evaluated for potential cytotoxic effects against melanoma (MelRm) and breast adenocarcinoma (MCF-7) cell lines. The bis-thiosemicarbazones in this study generally demonstrated superior cytotoxic activity against MelRm than MCF-7 in the absence of metal ion supplementation, but in most cases could not be considered superior to the reference thiosemicarbazone Dp44mT. The key structural features for the cytotoxic activity were the central metal binding atom on the aromatic core, the thiocarbonyl residue and the nature of substitution on the N4-terminus in terms of size and lipophilicity. The cytotoxicity of bis-thiosemicarbazone ligands improved significantly with Cu(II) supplementation, particularly against MCF-7 cells. The mechanism of cytotoxicity of bis-thiosemicarbazones was proposed to be dependent on the combined effect of metal mobilisation and ROS generation which is so called a "double-punch effect".