pyridine-2-carbaldehyde N(4)-p-methoxyphenylthiosemicarbazone | 92193-33-4

• 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: pyridine-2-carbaldehyde N(4)-p-methoxyphenylthiosemicarbazone
• 英文别名: 1-(2'-pyridinecarboxaldehyde)-4-(4'-methoxyphenyl)-3-thiosemicarbazone；1-(4-Methoxyphenyl)-3-(pyridin-2-ylmethylideneamino)thiourea
• CAS: 92193-33-4
• 化学式: C₁₄H₁₄N₄OS
• 分子量: 286.357
• InChiKey: ACMYXIUIPBOQHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 pyridine-2-carbaldehyde N(4)-p-methoxyphenylthiosemicarbazone 以 乙醇 为溶剂， 生成 [Cu(pyridine-2-carbaldehyde-N(4)-p-methoxyphenyl thiosemicarbazonate)Cl]
  参考文献：
  名称：

  Copper(II) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde: Crystal structure of a binuclear complex

  摘要：

  Ten copper(II) complexes {[(CuLCl)-Cl-1] (1), [(CuLNO3)-N-1](2) (2), [(CuLN3)-N-1](2) center dot 2/3HO (3), [CuL1](2)(ClO4)(2) center dot 2H(2)O (4), [(CuLCl)-Cl-2](2) (5), [(CuLN3)-N-2] (6), [Cu(HL2)SO4](2) center dot 4H(2)O (7), [Cu(HL2)(2)] (ClO4)(2) center dot 1/2EtOH (8), [(CuLCl)-Cl-3](2) (9), [CuL3 NCS] center dot 1/2H(2)O (10)) of three NNS donor thiosemicarbazone ligands {pyridine-2-carbaldehyde-N(4)-p-methoxyphenyl thiosemicarbazone [HL1], pyridine-2-carbaldehyde-N(4)-2-phenethyl thiosemicarbazone [HL2] and pyridine-2-carbaldehyde N(4)-(methyl), N(4)-(phenyl) thiosernicarbazone [HL3]) were synthesized and physico-chemically characterized. The crystal structure of compound 9 has been determined by X-ray diffraction studies and is found that the dimer consists of two square pyramidal Cu(II) centers linked by two chlorine atoms. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2006.09.091
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-(4-甲氧基苯基)-3-硫代氨基甲酰肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以66%的产率得到pyridine-2-carbaldehyde N(4)-p-methoxyphenylthiosemicarbazone
  参考文献：
  名称：

  Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells

  摘要：

  We have recently identified a new class of compounds that selectively kill cells that express P-glycoprotein (P-gp, MDR1), the ATPase efflux pump that confers multidrug resistance on cancer cells. Several isatin-beta-thiosemicarbazones from our initial study have been validated and a range of analogues synthesized and tested. A number demonstrated improved MDR1-selective activity over the lead, NSC73306 (1). Pharmacophores for cytotoxicity and MDR1 selectivity were generated to delineate the structural features required for activity. The MDR1-selective pharmacophore highlights the importance of aromatic/hydrophobic features at the N4 position of the thiosemicarbazone and the reliance on the isatin moiety as key bioisosteric contributors. Additionally, a quantitative structure-activity relationship (QSAR) model that yielded a cross-validated correlation coefficient of 0.85 effectively predicts the cytotoxicity of untested thiosemicarbazones. Together, the models serve as effective approaches for predicting structures with MDR1-selective activity and aid in directing the search for the mechanism of action of 1.

  DOI：

  10.1021/jm800861c

文献信息

• Nickel(II) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde: Crystal structures, spectral aspects and Hirshfeld surface analysis
  作者：P.F. Rapheal、E. Manoj、M.R. Prathapachandra Kurup、Hoong-Kun Fun

  DOI：10.1016/j.molstruc.2021.130362

  日期：2021.8

  Seven Ni(II) complexes [NiL12]•2H2O (1), [Ni2L22SO4]•1½H2O (2), [Ni(HL2)2](NO3)2•H2O•EtOH (3), [NiL2(HL2)]OAc•3H2O (4), [Ni(HL2)2](ClO4)2•2H2O (5), [NiL3OAc]•2½H2O (6), [NiL3NO3]•3H2O (7)} of three thiosemicarbazone ligands, viz•pyridine-2-carbaldehyde-N(4)-p-methoxyphenyl thiosemicarbazone (HL1), pyridine-2-carbaldehyde N(4)-phenethyl thiosemicarbazone (HL2) and pyridine-2-carbaldehyde-N(4)-pyridyl

  七的Ni（II）络合物[NIL 1 2 ] • 2H 2 O（1），[倪2大号2 2 SO 4 ] • 1½H 2 O（2）， [镍（HL 2）2 ]（NO 3）2 • H 2 O • EtOH（3），[NiL 2（HL 2）] OAc • 3H 2 O（4），[Ni（HL 2）2 ]（ClO 4）2• 2H 2 O（5），[NIL 3 OAC] • 2½H 2 O（6），[NIL 3 NO 3 ] • 3H 2 O（7的）} 3个缩氨基硫脲配位体，即•吡啶-2-甲醛-N（ 4）-对甲氧基苯基硫代半脲（HL 1），吡啶-2-甲醛N（4）-苯乙基硫代半脲（HL 2）和吡啶-2-甲醛-N（4）-吡啶基硫代半脲[HL 3通过部分元素分析，摩尔电导率测量，电子，红外光谱研究和磁化率测量，合成了[]和理化性质。在配合物中，硫代半氨基甲酮以硫酮形式和去质子化的硫醇盐形式配位。吡啶氮，偶氮甲碱氮和硫醇
• Syntheses and EPR spectral studies of manganese(II) complexes derived from pyridine-2-carbaldehyde based N(4)-substituted thiosemicarbazones: Crystal structure of one complex
  作者：P.F. Rapheal、E. Manoj、M.R. Prathapachandra Kurup

  DOI：10.1016/j.poly.2007.07.028

  日期：2007.10

  Five manganese(II) complexes [MnL21] center dot H2O center dot EtOH (1), [Mn(L-1)(HL1)]OAc (2), [MnL22] center dot 3H(2)O (3), [MnL23] center dot 3H(2)O (4) and [Mn(HL3)(2)](SCN)(2) center dot MeOH (5)} of three NNS donor N(4)-substituted thiosemicarbazone ligands (pyridine-2-carbaldehyde N(4)p-methoxyphenyl thiosemicarbazone [HL1], pyridine-2-carbaldehyde N(4)-2-phenethyl thiosemicarbazone [HL2] and pyridine-2-carbaldehyde N(4)-methyl, N(4)-phenyl thiosemicarbazone [HL3]) were synthesized and physico-chemically characterized. Compound 1 crystallized as [MnL21] center dot H2O and its structure has been determined by X-ray diffraction studies. It is found to have a distorted octahedral geometry. EPR spectra in DMF solutions at 77 K show hyperfine sextets with low intensity forbidden lines lying between each of the two main hyperfine lines. (C) 2007 Elsevier Ltd. All rights reserved.
• Structural and spectral studies of novel Co(III) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde
  作者：P.F. Rapheal、E. Manoj、M.R. Prathapachandra Kurup、E. Suresh

  DOI：10.1016/j.poly.2006.08.029

  日期：2007.2

  Seven bis(ligand) Co(III) complexes [CoL21]NO3 (.) H2O (1), [CoL21]Cl (.) 2H(2)O (2),[CoL21]ClO4, (3), [CoL22]NO3 (4), [CoL22]Cl. 2H(2)O (5), [CoL23]Br (.) 2H(2)O (6), [CoL23]ClO4 (.) H2O (7)} of three thiosemicarbazone ligands pyridine-2-carbaidehyde-N(4)-p-methoxy-phenyl thiosemicarbazone [HL1], pyridine-2-carbaldehyde-N(4)-2-phenylethyl thiosernicarbazone [HL2] and pyridine-2-carbaldehyde-N(4)-(methyl),N(4)-(phenyl) thiosemicarbazone [HL3]} were synthesized and physico-chemically characterized. All complexes are assigned octahedral geometries on the basis of spectral studies. The ligands deprotonate and coordinate by means of pyridine nitrogen, azomethine nitrogen, and thiolate sulfur atoms. The single crystal X-ray structures of HL3 and two nitrate compounds are discussed. The structural studies corroborate the spectral characterization. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Activity, and Pharmacophore Development for Isatin-β-thiosemicarbazones with Selective Activity toward Multidrug-Resistant Cells
  作者：Matthew D. Hall、Noeris K. Salam、Jennifer L. Hellawell、Henry M. Fales、Caroline B. Kensler、Joseph A. Ludwig、Gergely Szakács、David E. Hibbs、Michael M. Gottesman

  DOI：10.1021/jm800861c

  日期：2009.5.28

  We have recently identified a new class of compounds that selectively kill cells that express P-glycoprotein (P-gp, MDR1), the ATPase efflux pump that confers multidrug resistance on cancer cells. Several isatin-beta-thiosemicarbazones from our initial study have been validated and a range of analogues synthesized and tested. A number demonstrated improved MDR1-selective activity over the lead, NSC73306 (1). Pharmacophores for cytotoxicity and MDR1 selectivity were generated to delineate the structural features required for activity. The MDR1-selective pharmacophore highlights the importance of aromatic/hydrophobic features at the N4 position of the thiosemicarbazone and the reliance on the isatin moiety as key bioisosteric contributors. Additionally, a quantitative structure-activity relationship (QSAR) model that yielded a cross-validated correlation coefficient of 0.85 effectively predicts the cytotoxicity of untested thiosemicarbazones. Together, the models serve as effective approaches for predicting structures with MDR1-selective activity and aid in directing the search for the mechanism of action of 1.
• Copper(II) complexes of N(4)-substituted thiosemicarbazones derived from pyridine-2-carbaldehyde: Crystal structure of a binuclear complex
  作者：P.F. Rapheal、E. Manoj、M.R. Prathapachandra Kurup

  DOI：10.1016/j.poly.2006.09.091

  日期：2007.3

  Ten copper(II) complexes [(CuLCl)-Cl-1] (1), [(CuLNO3)-N-1](2) (2), [(CuLN3)-N-1](2) center dot 2/3HO (3), [CuL1](2)(ClO4)(2) center dot 2H(2)O (4), [(CuLCl)-Cl-2](2) (5), [(CuLN3)-N-2] (6), [Cu(HL2)SO4](2) center dot 4H(2)O (7), [Cu(HL2)(2)] (ClO4)(2) center dot 1/2EtOH (8), [(CuLCl)-Cl-3](2) (9), [CuL3 NCS] center dot 1/2H(2)O (10)) of three NNS donor thiosemicarbazone ligands pyridine-2-carbaldehyde-N(4)-p-methoxyphenyl thiosemicarbazone [HL1], pyridine-2-carbaldehyde-N(4)-2-phenethyl thiosemicarbazone [HL2] and pyridine-2-carbaldehyde N(4)-(methyl), N(4)-(phenyl) thiosernicarbazone [HL3]) were synthesized and physico-chemically characterized. The crystal structure of compound 9 has been determined by X-ray diffraction studies and is found that the dimer consists of two square pyramidal Cu(II) centers linked by two chlorine atoms. (c) 2006 Elsevier Ltd. All rights reserved.