2-(pyridin-2-ylmethylene)-N-(4'-tolyl)hydrazinecarbothioamide | 1154407-76-7

• 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: 2-(pyridin-2-ylmethylene)-N-(4'-tolyl)hydrazinecarbothioamide
• 英文别名: N(4)-para-tolyl 2-formylpyridine thiosemicarbazone；H2Fo4pT；1-(4-methylphenyl)-3-[(E)-pyridin-2-ylmethylideneamino]thiourea
• CAS: 1154407-76-7
• 化学式: C₁₄H₁₄N₄S
• 分子量: 270.358
• InChiKey: SUMXLQKGNVWFFU-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 2-(pyridin-2-ylmethylene)-N-(4'-tolyl)hydrazinecarbothioamide 以 乙醇 为溶剂， 以88%的产率得到chloro(N(4)-p-tolyl-2-formylpyridine-thiosemicarbazonato)copper(II)
  参考文献：
  名称：

  Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones

  摘要：

  Five copper(II) complexes with N(4)-ortho, N(4)-meta and N(4)-para-tolyl thiosemicarbazones derived from 2-formyl and 2-acetylpyridine were obtained and thoroughly characterized. The crystal structure of N(4)-meta-tolyl-2-acetylpyridine thiosemicarbazone (H2Ac4mT) was determined, as well as that of its copper(II) complex [Cu(2Ac4mT)Cl], which contains an anionic ligand and a chloride in the coordination sphere of the metal. The in vitro antimicrobial activities of all thiosemicarbazones and their copper(II) complexes were tested against Salmonella typhinturium and Candida albicans. Upon coordination a substantial decrease in the minimum inhibitory concentration, from 225 to 1478 mu mol L-1 for the thiosernicarbazones to 5-30 mu mol L-1 for the complexes was observe against the growth of Salmonella typhimurium and from 0.7-26 to 0.3-7 mu mol L-1 against the growth of C albicans, suggesting that complexation to copper(II) could be an interesting strategy of dose reduction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.03.002
• 作为产物：
  描述：

  对甲苯异硫氰酸酯 在 吡咯 、 一水合肼 、 异丙醇 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 2-(pyridin-2-ylmethylene)-N-(4'-tolyl)hydrazinecarbothioamide
  参考文献：
  名称：

  二芳基取代氨基硫脲：开发新德里金属-β-内酰胺酶-1抑制剂的有效支架

  摘要：

  由新德里金属-β-内酰胺酶（NDM-1）引起的超级细菌感染已成为一种新兴的公共卫生威胁。由于 NDM-1 在病原菌之间穿梭，因此抑制 NDM-1 已被证明具有挑战性。构建了一种有效的支架，二芳基取代的缩氨基硫脲，并用金属-β-内酰胺酶 (MβLs) 进行了测定。获得的 26 个分子特异性抑制 NDM-1，IC 50 0.038–34.7 µM 范围（1e、2e和3d除外），1c是最有效的抑制剂（IC 50 = 0.038 µM）。合成缩氨基硫脲的构效关系表明，二芳基取代物，特别是 2-吡啶和 2-羟基苯提高了抑制剂的抑制活性。缩氨基硫脲对大肠杆菌-NDM-1表现出协同抗分枝杆菌作用，导致美罗培南的 MIC 降低 2-512 倍，而1c恢复抗生素对临床分离株的 16-256-、16- 和 2 倍的活性ECs、肺炎克雷伯菌和铜绿假单胞菌分别含有 NDM-1。此外，小鼠实验表明，1c与美罗培南具

  DOI：

  10.1016/j.bioorg.2020.104576

文献信息

• Synthesis and characterization of some biologically active ruthenium(II) complexes of thiosemicarbazones of pyridine 2-aldehyde and thiophene 2-aldehyde involving some ring substituted 4-phenylthiosemicarbazides and 4-cyclohexylthiosemicarbazide. Crystal structure of cis-[Ru(PPh3)2(L6H)2](ClO4)2·2H2O [L6H=4-(cyclohexyl) thiosemicarbazone of pyridine 2-aldehyde]
  作者：Parbati Sengupta、Rupam Dinda、Saktiprosad Ghosh、William S Sheldrick

  DOI：10.1016/s0277-5387(02)01363-3

  日期：2003.2

  techniques. Electrochemical behavior of the complexes has been examined by cyclic voltammetry. Structure of one of the complexes cis-[Ru(PPh3)2(L6H)2](ClO4)2·2H2O, has been solved by single crystal X-ray diffraction technique. All the ligands are found to be chelated to the ruthenium(II) center in its thione form through its imine nitrogen and the thione sulfur. The pyridine ring nitrogen remained uncoordinated

  摘要合成了一系列潜在的NNS三齿状但功能上为NS二齿螯合配体的钌（II）配合物，它们是吡啶2-醛和噻吩2-醛（LH）的4-取代的4-苯基和4-环己基硫代半缩氮酮。使用Ru（PPh3）3Cl2作为起始原料。该配合物具有通式[Ru（PPh3）2（LH）2] X2，[L1H，L2H，L3H，L4H，L5H和L6H为4-（对氟苯基），4-（对氯苯基）4-吡啶2-醛和L7H的（对-碘苯基），4-（对-羟基苯基），4-（对-甲基苯基）和4-（对-环己基）硫代半氨基甲酮是噻吩2-醛的4-环己基硫代半碳酮（图1）和X = ClO4，PF6]。还合成了复合物[Ru（bipy）（L6H）2]（ClO4）2。所有的络合物都通过元素分析，溶液中电导的测量，在室温和光谱技术下的磁化率。通过循环伏安法检查了配合物的电化学行为。通过单晶X射线衍射技术已经解决了一种顺式[[Ru（PPh3）2（L6H）2]（ClO4）2·
• Fujikawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 1231,1233
  作者：Fujikawa et al.

  DOI：——

  日期：——
• Pape, Veronika F.S.; Tóth, Szilárd; Füredi, András, European Journal of Medicinal Chemistry, 2016, vol. 117, p. 335 - 354
  作者：Pape, Veronika F.S.、Tóth, Szilárd、Füredi, András、Szebényi, Kornélia、Lovrics, Anna、Szabó, Pál、Wiese, Michael、Szakács, Gergely

  DOI：——

  日期：——
• Diaryl-substituted thiosemicarbazone: A potent scaffold for the development of New Delhi metallo-β-lactamase-1 inhibitors
  作者：Jia-Qi Li、Le-Yun Sun、Zhihui Jiang、Cheng Chen、Han Gao、Jia-Zhu Chigan、Huan-Huan Ding、Ke-Wu Yang

  DOI：10.1016/j.bioorg.2020.104576

  日期：2021.2

  superbug infection caused by New Delhi metallo-β-lactamase (NDM-1) has become an emerging public health threat. Inhibition of NDM-1 has proven challenging due to its shuttling between pathogenic bacteria. A potent scaffold, diaryl-substituted thiosemicarbazone, was constructed and assayed with metallo-β-lactamases (MβLs). The obtained twenty-six molecules specifically inhibited NDM-1 with IC50 0.038–34.7 µM

  由新德里金属-β-内酰胺酶（NDM-1）引起的超级细菌感染已成为一种新兴的公共卫生威胁。由于 NDM-1 在病原菌之间穿梭，因此抑制 NDM-1 已被证明具有挑战性。构建了一种有效的支架，二芳基取代的缩氨基硫脲，并用金属-β-内酰胺酶 (MβLs) 进行了测定。获得的 26 个分子特异性抑制 NDM-1，IC 50 0.038–34.7 µM 范围（1e、2e和3d除外），1c是最有效的抑制剂（IC 50 = 0.038 µM）。合成缩氨基硫脲的构效关系表明，二芳基取代物，特别是 2-吡啶和 2-羟基苯提高了抑制剂的抑制活性。缩氨基硫脲对大肠杆菌-NDM-1表现出协同抗分枝杆菌作用，导致美罗培南的 MIC 降低 2-512 倍，而1c恢复抗生素对临床分离株的 16-256-、16- 和 2 倍的活性ECs、肺炎克雷伯菌和铜绿假单胞菌分别含有 NDM-1。此外，小鼠实验表明，1c与美罗培南具
• Coordination to copper(II) strongly enhances the in vitro antimicrobial activity of pyridine-derived N(4)-tolyl thiosemicarbazones
  作者：Isolda C. Mendes、Juliana P. Moreira、Antonio S. Mangrich、Solange P. Balena、Bernardo L. Rodrigues、Heloisa Beraldo

  DOI：10.1016/j.poly.2007.03.002

  日期：2007.8

  Five copper(II) complexes with N(4)-ortho, N(4)-meta and N(4)-para-tolyl thiosemicarbazones derived from 2-formyl and 2-acetylpyridine were obtained and thoroughly characterized. The crystal structure of N(4)-meta-tolyl-2-acetylpyridine thiosemicarbazone (H2Ac4mT) was determined, as well as that of its copper(II) complex [Cu(2Ac4mT)Cl], which contains an anionic ligand and a chloride in the coordination sphere of the metal. The in vitro antimicrobial activities of all thiosemicarbazones and their copper(II) complexes were tested against Salmonella typhinturium and Candida albicans. Upon coordination a substantial decrease in the minimum inhibitory concentration, from 225 to 1478 mu mol L-1 for the thiosernicarbazones to 5-30 mu mol L-1 for the complexes was observe against the growth of Salmonella typhimurium and from 0.7-26 to 0.3-7 mu mol L-1 against the growth of C albicans, suggesting that complexation to copper(II) could be an interesting strategy of dose reduction. (c) 2007 Elsevier Ltd. All rights reserved.