6-methyl-2-formyl4N-dimethylthiosemicarbazone | 210700-63-3

• 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: 6-methyl-2-formyl4N-dimethylthiosemicarbazone
• 英文别名: 1,1-Dimethyl-3-[(6-methylpyridin-2-yl)methylideneamino]thiourea
• CAS: 210700-63-3
• 化学式: C₁₀H₁₄N₄S
• 分子量: 222.314
• InChiKey: UGCNWDAIRROYFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  6-甲基-2-吡啶甲醛 、 6-methyl-2-formyl4N-dimethylthiosemicarbazone 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 4,4-二甲基-3-氨基硫脲单水合物
  参考文献：
  名称：

  基于修饰的人血清白蛋白IB亚域中的His146残基开发抗癌铜（II）多靶标前药

  摘要：

  设计具有改善的体内递送和治疗效率的多靶点抗癌药物提出了巨大的挑战。因此，我们建议基于棕榈酸（PA）修饰的人血清白蛋白（HSA-PA）IB亚域中的His146残基，设计一种衍生自硫半脲的抗癌多靶标金属前药。研究了六种Cu（II）化合物与6-甲基-2-甲酰基吡啶-4 N-取代的硫代半氨基甲酮的结构-活性关系，然后证实了4b在癌细胞DNA和蛋白质中的多靶标能力。HSA–PA– 4b复合物（HSA–PA– 4b）的结构揭示了4b结合到修饰的HSA的IB子结构域，并且His146取代4b中的硝酸盐配体，与Cu 2+配位，而PA通过与Lys199和His242形成氢键的羧基与IIA子结构域复合。体内数据显示4b和HSA–PA– 4b复合物抑制肺肿瘤的生长，并且PA修饰的HSA复合物的靶向能力和治疗功效强于单独的4b。

  DOI：

  10.1021/acs.molpharmaceut.8b00045

文献信息

• Synthesis, characterization, antifungal properties and X-ray crystal structures of five- and six-coordinate copper(II) complexes of the 6-methyl-2-formylpyridine4N-dimethylthiosemicarbazone
  作者：M.Akbar Ali、Aminul H Mirza、A Monsur、S Hossain、M Nazimuddin

  DOI：10.1016/s0277-5387(01)00724-0

  日期：2001.4

  Copper(II) complexes of formulas, [Cu(NNS)(NO3)(H2O)].H2O and [Cu(NNS)(2)] (NNS = anionic form of the 6-methyl-2formylpyridine(4)N-dimethylthiosemicarbazone) have been synthesized and characterized by a variety of physico-chemical techniques. Magnetic and spectroscopic data support a five-coordinate structure for the [Cu(NNS)(NO3)(H2O)].H2O complex and a distorted octahedral structure for the [Cu(NNS)(2)] complex. The crystal structures of both complexes have also been determined by X-ray diffraction. The mono-ligated nitrate-complex has a five-coordinate geometry, with the thiosemicarbazone ligand coordinated to the copper(II) ion as a uninegatively charged NNS tridentate chelating agent via the pyridine nitrogen atom, the azomethine nitrogen atom and the thiolate sulfur atom. The fourth and fifth coordination positions around the copper(II) ion are occupied by the nitrate and aqua ligands, respectively. The bis-ligand copper(II) complex, [Cu(NNS)(2)] has a distorted octahedral structure with two uninegatively charged tridentate NNS thiosemicarbazone ligands coordinated to the copper(II) ion via the pyridine nitrogen atoms, the azomethine nitrogen atoms and the mercaptide sulfur atoms in a meridional arrangement. The ligand is fungitoxic against the phytopathogenic fungi, A. alternata, F.equiseti and M. phaseolina but the complexes are less active than the free ligand. (C) 2001 Published by Elsevier Science Ltd.
• Developing an Anticancer Copper(II) Multitarget Pro-Drug Based on the His146 Residue in the IB Subdomain of Modified Human Serum Albumin
  作者：Jun Wang、Yi Gou、Zhenlei Zhang、Ping Yu、Jinxu Qi、Qipin Qin、Hongbin Sun、Xiaoyang Wu、Hong Liang、Feng Yang

  DOI：10.1021/acs.molpharmaceut.8b00045

  日期：2018.6.4

  efficiency in vivo presents a great challenge. Thus, we proposed to design an anticancer multitarget metal pro-drug derived from thiosemicarbazone based on the His146 residue in the IB subdomain of palmitic acid (PA)-modified human serum albumin (HSA-PA). The structure–activity relationship of six Cu(II) compounds with 6-methyl-2-formylpyridine-4N-substituted thiosemicarbazones were investigated, and then

  设计具有改善的体内递送和治疗效率的多靶点抗癌药物提出了巨大的挑战。因此，我们建议基于棕榈酸（PA）修饰的人血清白蛋白（HSA-PA）IB亚域中的His146残基，设计一种衍生自硫半脲的抗癌多靶标金属前药。研究了六种Cu（II）化合物与6-甲基-2-甲酰基吡啶-4 N-取代的硫代半氨基甲酮的结构-活性关系，然后证实了4b在癌细胞DNA和蛋白质中的多靶标能力。HSA–PA– 4b复合物（HSA–PA– 4b）的结构揭示了4b结合到修饰的HSA的IB子结构域，并且His146取代4b中的硝酸盐配体，与Cu 2+配位，而PA通过与Lys199和His242形成氢键的羧基与IIA子结构域复合。体内数据显示4b和HSA–PA– 4b复合物抑制肺肿瘤的生长，并且PA修饰的HSA复合物的靶向能力和治疗功效强于单独的4b。