(Z)-2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide | 1342898-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide
• 英文别名: 2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide
• CAS: 1342898-07-0
• 化学式: C₁₉H₁₈ClN₅OS
• 分子量: 399.904
• InChiKey: CPEFLIXOEBZZLQ-OQKWZONESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.08
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide 、 copper diacetate 在 CH₃COONa 作用下， 以 乙醇 、 水 为溶剂， 以66.76%的产率得到Cu(2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide(-2H))(water)
  参考文献：
  名称：

  Synthesis, spectroscopic characterization and DNA nuclease activity of Cu(II) complexes derived from pyrazolone based NSO-donor Schiff base ligands

  摘要：

  Two neutral mononuclear Cu(II) complexes have been prepared in EtOH using Schiff bases derived from 4-toluoyl pyrazolone and thiosemicarbazide. Both the ligands have been characterized on the basis of elemental analysis, IR, H-1 NMR, C-13 NMR and mass spectral data. The molecular geometry of one of these ligands has been determined by single crystal X-ray study. It reveals that these ligands exist in amine-one tautomeric form in the solid state. Microanalytical data, Cu-estimation, molar conductivity, magnetic measurements, IR, UV-Visible, FAB-Mass, TG-DTA data and ESR spectral studies were used to confirm the structures of the complexes. Electronic absorption and IR spectra of the complexes suggest a square-planar geometry around the central metal ion. The interaction of complexes with pET30a plasmid DNA was investigated by spectroscopic measurements. Results suggest that the copper complexes bind to DNA via an intercalative mode and can quench the fluorescence intensity of EB bound to DNA. The interaction between the complexes and DNA has also been investigated by agarose gel electrophoresis, interestingly, we found that the copper(II) complexes can cleave circular plasmid DNA to nicked and linear forms. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2011.09.039
• 作为产物：
  描述：

  MCPMP 、 氨基硫脲 以 乙醇 为溶剂， 反应 6.0h， 以85.33%的产率得到(Z)-2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene)hydrazinecarbothioamide
  参考文献：
  名称：

  A new pyrazolone based ternary Cu(II) complex: Synthesis, characterization, crystal structure, DNA binding, protein binding and anti-cancer activity towards A549 human lung carcinoma cells with a minimum cytotoxicity to non-cancerous cells

  摘要：

  With the aim of exploring the anticancer properties of coordination compounds, we report for the first time the synthesis of the new ternary complex [Cu(TMCPMP-TS)(Phen)] (TMCPMP-TS; (Z)-2-((1-(3-chlorophenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(p-tolyl)methylene) hydrazinecarbothioamide and Phen; 1,10-phenanthroline). The complex was characterized by various techniques, including Xray crystallography which showed that the geometry of the metal centre was between square pyramidal and trigonal bipyramidal. The interaction with calf-thymus DNA showed binding through intercalation. The protein binding ability with bovine serum albumin revealed a stronger binding of complex as compared to the free ligands. The anticancer activity of the complex was investigated by exposing it to the A549 (human lung cancer) cell line, which showed mitochondrial damage via an oxidative mechanism. After 24 h treatment, the complex arrested S and G2/M phases in the cell cycle progression and induced cell death. The results envisaged herein indicate that Cu(TMCPMP-TS)(Phen) holds ample merit to develop it as a therapeutic agent against cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.08.051