di-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone | 847867-85-0

• 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: di-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone
• 英文别名: di-2-pyridyl ketone N(4)-methyl, N(4)-phenylthiosemicarbazone；3-(Dipyridin-2-ylmethylideneamino)-1-methyl-1-phenylthiourea；3-(dipyridin-2-ylmethylideneamino)-1-methyl-1-phenylthiourea
• CAS: 847867-85-0
• 化学式: C₁₉H₁₇N₅S
• 分子量: 347.443
• InChiKey: XTRLGFDFFXTJRS-UHFFFAOYSA-N

物化性质

• 沸点：
  515.2±48.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(ll) bromide 、 di-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone 以 甲醇 、 氯仿 为溶剂， 以33%的产率得到[Cu(di-2-pyridyl ketone N(4)-methyl, N(4)-phenylthiosemicarbazone-1H)Br]2
  参考文献：
  名称：

  Novel binuclear copper(II) complexes of di-2-pyridyl ketone N(4)-methyl, N(4)-phenylthiosemicarbazone: Structural and spectral investigations

  摘要：

  Four binuclear complexes [Cu(dptsc)Cl](2) center dot 3H(2)O (1), [Cu(dptsc)Br](2) (2), [Cu(dptsc)(p-N-3)](2) (3) and [Cu(dptsc)(NO3)](2) center dot H2O (4) (where Hdptsc = di-2-pyridyl ketone N(4)-methyl, N(4)-phenylthiosemicarbazone) have been synthesized and physicochemically characterized. Each Cu(II) atom in the monomeric unit exists in a penta-coordinate environment. The molecular structures of [Cu(dptsc)Br](2) and [Cu(dptsc)(mu-N-3)](2) are resolved by single-crystal X-ray diffraction studies. Both the crystals are centrosymmetric dimers where each ligand unit coordinates through one of the pyridyl nitrogens, azomethine nitrogen and thiolate sulfur to Cu(II). A distorted square pyramidal geometry is observed around Cu(II) for both the complexes, where the N(2) nitrogen of the second ligand unit coordinates to the first Cu(II) center in compound 2 and N(6) nitrogen of the azido group bridges both the Cu(II) centers in compound 3. Spectral characterization corroborate the structural studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.03.064
• 作为产物：
  描述：

  2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid 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 di-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone
  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

• Increased generation of intracellular reactive oxygen species initiates selective cytotoxicity against the MCF-7 cell line resultant from redox active combination therapy using copper–thiosemicarbazone complexes
  作者：Fady N. Akladios、Scott D. Andrew、Christopher J. Parkinson

  DOI：10.1007/s00775-016-1350-2

  日期：2016.6

  The combination of cytotoxic copper-thiosemicarbazone complexes with phenoxazines results in an up to 50-fold enhancement in the cytotoxic potential of the thiosemicarbazone against the MCF-7 human breast adenocarcinoma cell line over the effect attributable to drug additivity-allowing minimization of the more toxic copper-thiosemicarbazone component of the therapy. The combination of a benzophenoxazine with all classes of copper complex examined in this study proved more effective than combinations of the copper complexes with related isoelectronic azines. The combination approach results in rapid elevation of intracellular reactive oxygen levels followed by apoptotic cell death. Normal fibroblasts representative of non-cancerous cells (MRC-5) did not display a similar elevation of reactive oxygen levels when exposed to similar drug levels. The minimization of the copper-thiosemicarbazone component of the therapy results in an enhanced safety profile against normal fibroblasts.
• Di-2-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone
  作者：Varughese Philip、V. Suni、M. R. Prathapachandra Kurup

  DOI：10.1107/s0108270104025235

  日期：2004.12.15

  The molecule of the title compound, C19H17N5S, adopts a Z configuration about the azomethine bond and exists as the thione tautomer. The overall structure of the molecule is distributed in four different planes. An intramolecular hydrogen bond involving the pyridyl N atom and the H atom attached to the hydrazine N atom leads to the formation of a six- membered ring.
• Manganese(II) complexes of substituted di-2-pyridyl ketone thiosemicarbazones: Structural and spectral studies
  作者：Varughese Philip、V. Suni、Maliyeckal R. Prathapachandra Kurup、Munirathinam Nethaji

  DOI：10.1016/j.saa.2005.07.013

  日期：2006.5

  The reaction between manganese(II) acetate and two substituted thiosemicarbazones derived from di-2-pyridyl ketone (HL) in 1:2 molar ratio produces new complexes of general formula [MnL2]. The thiosemicarbazone moiety in HL deprotonates and gets coordinated to Mn(II) through the azomethine nitrogen, one of the pyridyl nitrogens, and the thiolate sulfur in both the complexes. The crystal structure of [MnL2] was established by single crystal X-ray diffraction and the compound crystallizes into a monoclinic lattice with P2(1)/c space group. Manganese(11) exists in a distorted octahedral geometry in the complexes. (c) 2005 Elsevier B.V. All rights reserved.