6-methylpyridine-2-carboxaldehydethiosemicarbazone | 6853-69-6

• 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-methylpyridine-2-carboxaldehydethiosemicarbazone
• 英文别名: 6-methylpyridine-2-yl methylene hydrazine-1-carbothioamide；6-methyl-2-formylpyridinethiosemicarbazone；[(6-methylpyridin-2-yl)methylideneamino]thiourea
• CAS: 6853-69-6
• 化学式: C₈H₁₀N₄S
• 分子量: 194.26
• InChiKey: RGSKQRUEJICXLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 6-methylpyridine-2-carboxaldehydethiosemicarbazone 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到
  参考文献：
  名称：

  Synthesis, spectral characterization, and anticancer activity of 6-methylpyridine-2-carbaldehdyethiosemicarbazone and its complexes; crystal structure and DFT calculations of [Pd(mpyptsc)Cl]·DMSO

  摘要：

  DOI：

  10.1080/00958972.2014.942224
• 作为产物：
  描述：

  6-甲基-2-吡啶甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 6-methylpyridine-2-carboxaldehydethiosemicarbazone
  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

• Exploring Novel Pyridine Carboxamide Derivatives as Urease Inhibitors: Synthesis, Molecular Docking, Kinetic Studies and ADME Profile
  作者：Ayesha Naseer、Faisal Abdulrhman Osra、Asia Naz Awan、Aqeel Imran、Abdul Hameed、Syed Adnan Ali Shah、Jamshed Iqbal、Zainul Amiruddin Zakaria

  DOI：10.3390/ph15101288

  日期：——

  07 ± 0.043 µM, 2.18 ± 0.058 µM both possessed significant activity. Furthermore, molecular docking and kinetic studies were performed for the most potent inhibitors to demonstrate the binding mode of the active pyridine carbothioamide with the enzyme urease and its mode of interaction. The ADME profile also showed that all the synthesized molecules present oral bioavailability and high GI absorption

  与各种危及生命的病症例如胃癌和十二指肠癌相关的尿素分解细菌的耐药性的快速发展导致需要开发具有抗脲酶活性的新疗法。通过缩合反应合成了一系列具有新颖结构的吡啶甲酰胺和硫代甲酰胺衍生物，并研究了它们对脲酶的抑制作用。该系列中，5-氯吡啶-2基亚甲基肼硫甲酰胺(Rx-6)和吡啶2-基亚甲基肼甲酰胺(Rx-7) IC50 = 1.07 ± 0.043 µM、2.18 ± 0.058 µM均具有显着的活性。此外，对最有效的抑制剂进行了分子对接和动力学研究，以证明活性吡啶硫代甲酰胺与脲酶的结合模式及其相互作用模式。 ADME 曲线还表明，所有合成的分子均具有口服生物利用度和高胃肠道吸收。
• The preparation and characterization of some copper(II) Complexes of the 6-methyl-2-formylpyridine thiosemicarbazone and the x-ray crystal structure of the chloro(6-methyl-2-formylpyridinethiosemicabazonato) copper(II) complex
  作者：Mohammad A. Ali、Kanu K. Dey、Mohamed Nazimuddin、Frank E. Smith、Ray J. Butcher、Jerry P. Jasinski、John M. Jasinski

  DOI：10.1016/0277-5387(96)00003-4

  日期：1996.6

  Magnetic and spectral data support a square-planar structure for [Cu(NNS)X] (X = Cl, Br, NO 3 , CH 3 COO) and a distorted octahedral structure for [Cu(NNS) 2 ] · 0.5H 2 O. The crystal and molecular structure of [Cu(NSS)Cl] has been determined by X-ray diffraction. This complex has a distorted square-planar geometry with the copper(II) ion lying in an approximate plane of four coordinating atoms, three of which

  摘要通式为[Cu（NNS）X]·xH 2 O（NNS =由6-甲基吡啶-2-醛与硫代氨基脲缩合形成的带负电荷的三齿配体的铜（II）配合物； X = Cl，Br，NO 3和CH 3 COO； x = 0，1）和[Cu（NNS）2]·0.5H 2 O已制备并通过电导，磁，电子和红外光谱测量表征。磁性和光谱数据支持[Cu（NNS）X]的正方形平面结构（X = Cl，Br，NO 3，CH 3 COO）和[Cu（NNS）2]·0.5H 2 O的扭曲八面体结构通过X射线衍射确定了[Cu（NSS）Cl]的晶体和分子结构。该配合物的方形几何结构扭曲，铜（II）离子位于四个配位原子的近似平面中，其中三个来自6-甲基吡啶-2-羧甲醛硫代半脲，而第四个配位位点则被氯化物配体占据。硫半脲酮以硫醇盐形式存在，并通过吡啶氮原子，偶氮甲碱氮原子和硫醇硫原子与铜（II）离子配位。版权所有©1996 Elsevier Science
• Synthesis and characterization of some four- and five-coordinate copper(II) complexes of 6-methyl-2-formylpyridinethiosemicarbazone (HNNS) and the X-ray crystal structures of the [Cu(NNS)(CH3COO)(H2O)] and [Cu (HNNS) (H20) (S04)) - H2O complexes
  作者：Mohammad Akbar Ali、Nor Erawadi Hj Ibrahim、Ray J. Butcher、Jerry P. Jasinski、John M. Jasinski、Jeffrey C. Bryan

  DOI：10.1016/s0277-5387(97)00531-7

  日期：1998.5

  Copper(II) complexes of general formula, [Cu(NNS)(H2O)(x)X]. nH(2)O (NNS- = uninegatively charged tridentate thiosemicarbazone ligand formed from 6-methyl-2-formylpyridine; X = NCS-, CH3COO-, N-3(-); x = 0,1; n = 0.5, 1) and [Cu(HNNS)(H2O)(SO4)]. H2O have been synthesized and characterized by a variety of physico-chemical techniques. Magnetic and spectroscopic evidence support a square-planar structure for the [Cu(NNS)X] (X = NCS-, N-3(-)) complexes and a five-coordinate structure for the [Cu(HNNS)(H2O)(SO4)]. H2O complex. The crystal structures of the [Cu(NNS)(CH3COO)(H2O)] and [Cu(HNNS)(H2O)(SO4)]. H2O complexes have been determined by X-ray diffraction. The acetato complex has a distorted square-pyramidal geometry with the thiosemicarbazone ligand acting as a uninegatively charged tridentate NNS chelating agent and the fourth and fifth coordination positions of the copper(II) ion are occupied by a unidentate acetate and water ligand, respectively. The sulphate-complex is also five-coordinate with the thiosemicarbazone coordinated as a neutral NNS ligand and the fourth and fifth coordination sites are occupied by a water molecule and a unidentate sulphate ligand, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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。
• Synthesis, spectral characterization, and anticancer activity of 6-methylpyridine-2-carbaldehdyethiosemicarbazone and its complexes; crystal structure and DFT calculations of [Pd(mpyptsc)Cl]·DMSO
  作者：Shadia A. Elsayed、Ian S. Butler、Denis F.R. Gilson、Bertrand J. Jean-Claude、Sahar I. Mostafa

  DOI：10.1080/00958972.2014.942224

  日期：2014.8.18