N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole
• 英文别名: 3,5-dimethyl-1-(N-methyl)thiocarbamylpyrazole；3,5-dimethyl-pyrazole-1-carbothioic acid methylamide；N,3,5-trimethylpyrazole-1-carbothioamide
• 化学式: C₇H₁₁N₃S
• 分子量: 169.25
• InChiKey: HDJMYZQNUZPYEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole 在 silver nitrate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成
  参考文献：
  名称：

  Synthesis, cytotoxic activity and DNA interaction of Pd(II) complexes bearing N′-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole

  摘要：

  A new series of complexes of general formulae [PdX2(tmdmPz)] {X = Cl (1), Br (2), I (3), SCN (4); tmdmPz = N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole} have been synthesized and characterized by elemental analysis, molar conductivities, IR, H-1 and C-13{H-1} NMR spectroscopy. In these complexes, the tmdmPz coordinates to Pd(II) center as a neutral N,S-chelating ligand. The geometries of the complexes have been optimized with the DFT method. Cytotoxicity evaluation against LM3 (mammary adenocarcinoma) and LP07 (lung adenocarcinoma) cell lines indicated that complexes 1-4 were more active than cisplatin. The binding of the complexes with a purine base (guanosine) was investigated by H-1 NMR and mass spectrometry, showing that the coordination of guanosine occurs through N7. Electrophoretic DNA migration studies showed that all of them modify the DNA tertiary structure. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.08.040
• 作为产物：
  描述：

  4-甲基氨基硫脲 、 乙酰丙酮 在 盐酸 作用下， 以 水 为溶剂， 生成 N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole
  参考文献：
  名称：

  带有1-亚氨基硫代-3,5-二甲基吡唑的钯（II）配合物：合成，细胞毒性，DNA结合和酶抑制研究

  摘要：

  四种通式为[PdCl（L n）（PPh 3）]的钯（II）化合物{ L 1 = 3,5-二甲基吡唑-1-亚氨基硫醇盐（1）; L 2＝ 3，5-二甲基-吡唑-N-甲基-1-亚氨基硫醇盐（2）；L 3＝ 3，5-二甲基吡唑-N-乙基-1-亚氨基硫酸酯（3）；L 4＝ 3，5-二甲基吡唑-N-苯基-1-亚氨基硫醇酯（4）；和PPh 3＝三苯基膦}已合成。新型合成的化合物已通过C，H和N元素分析，1D（1 H和13 C）和2D（HSQC和HMBC）NMR，MS，FT-IR和摩尔电导率测量进行了表征。配合物3的分子结构已经通过单晶X射线晶体学解析。48小时后，在DMSO / D 2 O（7：3）溶液中研究了复合物在溶液中的稳定性。所有自由配体和稳定的钯络合物的抗增殖活性2 - 4使用人乳腺肿瘤细胞系MCF-7，肺肿瘤细胞系A549和人胎儿肺成纤维细胞系MRC-5测定。复杂3对MCF-7细胞具有比顺

  DOI：

  10.1039/d0nj02825h

文献信息

• Synthesis and characterization of two tris-chelate complexes of cobalt(III) with 3,5-dimethyl-1-(N-methyl/ethyl)thiocarbamylpyrazole (HL1, HL2)—biologically important bidentate ligands with one ambidentate donor site
  作者：Anil Kumar Barik、Sachindranath Paul、Ray J. Butcher、Susanta Kumar Kar

  DOI：10.1016/s0277-5387(00)00523-4

  日期：2000.12

  Abstract Cobalt(III) complexes, of two potentially pyrazole-derived bidentate ligands (with one ambidentate donor site), 3,5-dimethyl-1-( N -methyl/ethyl)thiocarbamylpyrazole (HL 1 for N -methyl, HL 2 for N -ethyl) have been synthesized and characterized by elemental analyses, IR, UV–Vis and 1 H NMR spectral studies. The structure of Co(L 2 ) 3 has been determined by single-crystal X-ray diffraction

  摘要钴（III）络合物，由两个潜在的吡唑衍生的双齿配体（具有一个不明确的供体位点），3,5-二甲基-1-（N-甲基/乙基）硫代氨基甲酰基吡唑（对于N-甲基为HL 1，对于HL 2为HL 2） N-乙基）已经合成，并通过元素分析，IR，UV-Vis和1 H NMR光谱研究进行了表征。Co（L 2）3的结构已经通过单晶X射线衍射研究确定。配合物（三斜空间群P 1）具有扭曲的八面体结构，其无配位配位体通过吡唑环氮（叔）和硫代氨基甲酰基亚氨基氮原子与Co（III）离子配位作为单价二齿螯合剂。规则八面体几何形状的变形归因于平面二齿配体施加的立体化学限制。
• Copper (II) and nickel (II) complexes of pyrazole derived ligands: Synthesis, characterization and coordinating properties of two substituted thiocarbamyl pyrazoles, 3,5-dimethyl-1-N-methyl/ethyl thiocarbamyl pyrazole (HL1, HL2), potential ligands for biological interest. X-ray crystallographic studies of Ni (L2)2
  作者：Anil Kumar Barik、Prasun Bandyopadhyay、Susanta Kumar Kar

  DOI：10.1016/s0277-5387(98)00241-1

  日期：1998.12

  The solid complexes of Cu(II) with different counterions and Nio(II) having no counterions with 3,5-dimethyl-1-N-methyl thiocarbamylpyrazole (HL1) and 3,5-dimethyl-1-N-ethyl thiocarbamylpyrazole (HL2), the ligands having coordination function of the pyrazole ring and the thiocarbamido group, have been prepared and their geometries established on the basis of molar conductance, magnetic susceptibility, IR, UV and visible spectral data. Magnetic and spectral features indicate paramagnetic [Cu(HL1/HL2)X-2] (X = Cl, Br), [Cu(HL1/HL2)(2)] (ClO4)(2) as either planar or tetragonally distorted octahedral species with the ligands in the neutral "thione" form, while Ni(L-1/L-2)(2) as the diamagnetic square planar species with the ligands in the deprotonated "thiol" form. X-ray crystallographic studies of Ni(L-2)(2) has unambiguously proved the distorted square planar environment around the central nickel(II) ion; the ligand molecules are cis-coordinated to the nickel(II) ion. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Palladium(<scp>ii</scp>) complexes bearing 1-iminothiolate-3,5-dimethylpyrazoles: synthesis, cytotoxicity, DNA binding and enzymatic inhibition studies
  作者：Thales Reggiani de Moura、Renan Diego Zanetti、Debora Eduarda Soares Silva、Renan Lira de Farias、Antonio Eduardo Mauro、José Clayston Melo Pereira、Aline Aparecida de Souza、Fábio da Silva Siqueira、Wagner Alves de Souza Júdice、Mauro Almeida Lima、Fillipe Vieira Rocha、Victor Marcelo Deflon、Adelino Vieira de Godoy Netto

  DOI：10.1039/d0nj02825h

  日期：——

  and 13C) and 2D (HSQC and HMBC) NMR, MS, FT-IR, and molar electrical conductivity measurements. The molecular structure of complex 3 has been solved by single-crystal X-ray crystallography. The stability of the complexes in solution was studied in a DMSO/D2O (7 : 3) solution after 48 h. The antiproliferative activity of all free ligands and the stable palladium complexes 2–4 was assayed using the human

  四种通式为[PdCl（L n）（PPh 3）]的钯（II）化合物 L 1 = 3,5-二甲基吡唑-1-亚氨基硫醇盐（1）; L 2＝ 3，5-二甲基-吡唑-N-甲基-1-亚氨基硫醇盐（2）；L 3＝ 3，5-二甲基吡唑-N-乙基-1-亚氨基硫酸酯（3）；L 4＝ 3，5-二甲基吡唑-N-苯基-1-亚氨基硫醇酯（4）；和PPh 3＝三苯基膦}已合成。新型合成的化合物已通过C，H和N元素分析，1D（1 H和13 C）和2D（HSQC和HMBC）NMR，MS，FT-IR和摩尔电导率测量进行了表征。配合物3的分子结构已经通过单晶X射线晶体学解析。48小时后，在DMSO / D 2 O（7：3）溶液中研究了复合物在溶液中的稳定性。所有自由配体和稳定的钯络合物的抗增殖活性2 - 4使用人乳腺肿瘤细胞系MCF-7，肺肿瘤细胞系A549和人胎儿肺成纤维细胞系MRC-5测定。复杂3对MCF-7细胞具有比顺
• Synthesis, cytotoxic activity and DNA interaction of Pd(II) complexes bearing N′-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole
  作者：Carolina V. Barra、Fillipe V. Rocha、Arnaud Gautier、Laurent Morel、Marcela B. Quilles、Iracilda Z. Carlos、Oswaldo Treu-Filho、Regina C.G. Frem、Antonio E. Mauro、Adelino V.G. Netto

  DOI：10.1016/j.poly.2013.08.040

  日期：2013.11

  A new series of complexes of general formulae [PdX2(tmdmPz)] X = Cl (1), Br (2), I (3), SCN (4); tmdmPz = N'-methyl-3,5-dimethyl-1-thiocarbamoylpyrazole} have been synthesized and characterized by elemental analysis, molar conductivities, IR, H-1 and C-13H-1} NMR spectroscopy. In these complexes, the tmdmPz coordinates to Pd(II) center as a neutral N,S-chelating ligand. The geometries of the complexes have been optimized with the DFT method. Cytotoxicity evaluation against LM3 (mammary adenocarcinoma) and LP07 (lung adenocarcinoma) cell lines indicated that complexes 1-4 were more active than cisplatin. The binding of the complexes with a purine base (guanosine) was investigated by H-1 NMR and mass spectrometry, showing that the coordination of guanosine occurs through N7. Electrophoretic DNA migration studies showed that all of them modify the DNA tertiary structure. (C) 2013 Elsevier Ltd. All rights reserved.