2,2'-(1,3-phenylenebis(methanylylidene))bis(thiosemicarbazide) | 5445-15-8

• 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: 2,2'-(1,3-phenylenebis(methanylylidene))bis(thiosemicarbazide)
• 英文别名: Isophthalaldehyd-bis-thiosemicarbazon；isophthalaldehyde bis thiosemicarbazone；2,2'-(1,3-Phenylenedimethanylylidene)di(hydrazine-1-carboximidothioic acid)；[[3-[(carbamothioylhydrazinylidene)methyl]phenyl]methylideneamino]thiourea
• CAS: 5445-15-8
• 化学式: C₁₀H₁₂N₆S₂
• 分子量: 280.377
• InChiKey: BPBGBZSSUXXWPS-UHFFFAOYSA-N

物化性质

• 熔点：
  247 °C (decomp)
• 沸点：
  501.2±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-(1,3-phenylenebis(methanylylidene))bis(thiosemicarbazide) 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.3h， 生成 1,1'-(((1,3-phenylenebis(methaneylylidene))bis(hydrazin-1-yl-2-ylidene))bis(thiazole-2,5-diyl))bis(2,2-dimethylpropan-1-one)
  参考文献：
  名称：

  Efficient synthesis of new tetradentate ligands with potential applications for 64Cu PET-imaging

  摘要：

  We wish to report the synthesis of new tetradentate ligands in less than 3 h in good to excellent yields from a commercially available compound using microwave-assisted technology. First tests of complexation showed a high ability of these ligands to chelate Cu-64(II) in very diluted medium. These new systems have the potential to be used for nuclear medicine and particularly for PET-imaging. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.072
• 作为产物：
  描述：

  间苯二甲醛 、 氨基硫脲 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 2,2'-(1,3-phenylenebis(methanylylidene))bis(thiosemicarbazide)
  参考文献：
  名称：

  Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease

  摘要：

  A series of thirty (30) thiazole analogs were prepared, characterized by H-1 NMR, C-13 NMR and EI-MS and evaluated for Acetylcholinesterase and butyrylcholinesterase inhibitory potential. All analogs exhibited varied butyrylcholinesterase inhibitory activity with IC50 value ranging between 1.59 +/- 0.01 and 389.25 +/- 1.75 mu M when compared with the standard eserine (IC50, 0.85 +/- 0.0001 mu M). Analogs 15, 7, 12, 9, 14, 1, 30 with IC50 values 1.59 +/- 0.01, 1.77 +/- 0.01, 6.21 +/- 0.01, 7.56 +/- 0.01, 8.46 +/- 0.01, 14.81 +/- 0.32 and 16.54 +/- 0.21 mu M respectively showed excellent inhibitory potential. Seven analogs 15, 20, 19, 24, 28, 30 and 25 exhibited good acetylcholinesterase inhibitory potential with IC50 values 21.3 +/- 0.50, 35.3 +/- 0.64, 36.6 +/- 0.70, 44.81 +/- 0.81, 46.36 +/- 0.84, 48.2 +/- 0.06 and 48.72 +/- 0.91 mu M respectively. All other analogs also exhibited well to moderate enzyme inhibition. The binding mode of these compounds was confirmed through molecular docking. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.08.002

文献信息

• Thiosemicarbazones as Aedes aegypti larvicidal
  作者：João Bosco P. da Silva、Daniela Maria do A.F. Navarro、Aluizio G. da Silva、Geanne K.N. Santos、Kamilla A. Dutra、Diogo Rodrigo Moreira、Mozart N. Ramos、José Wanderlan P. Espíndola、Ana Daura T. de Oliveira、Dalci José Brondani、Ana Cristina L. Leite、Marcelo Zaldini Hernandes、Valéria R.A. Pereira、Lucas F. da Rocha、Maria Carolina A.B. de Castro、Beatriz C. de Oliveira、Que Lan、Kenneth M. Merz

  DOI：10.1016/j.ejmech.2015.04.061

  日期：2015.7

  A set of aryl- and phenoxymethyl-(thio)semicarbazones were synthetized, characterized and biologically evaluated against the larvae of Aedes aegypti (A. aegypti), the vector responsible for diseases like Dengue and Yellow fever. (Q)SAR studies were useful for predicting the activities of the compounds not included to create the QSAR model as well as to predict the features of a new compound with improved activity. Docking studies corroborated experimental evidence of AeSCP-2 as a potential target able to explain the larvicidal properties of its compounds. The trend observed between the in silica Docking scores and the in vitro pLC50 (equals -log LC50, at molar concentration) data indicated that the highest larvicidal compounds, or the compounds with the highest values for pLC50, are usually those with the higher docking scores (i.e., greater in silica affinity for the AeSCP-2 target). Determination of cytotoxicity for these compounds in mammal cells demonstrated that the top larvicide compounds are non-toxic. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Efficient synthesis of new tetradentate ligands with potential applications for 64Cu PET-imaging
  作者：Ewen Bodio、Karine Julienne、Sébastien G. Gouin、Alain Faivre-Chauvet、David Deniaud

  DOI：10.1016/j.bmcl.2010.12.072

  日期：2011.2

  We wish to report the synthesis of new tetradentate ligands in less than 3 h in good to excellent yields from a commercially available compound using microwave-assisted technology. First tests of complexation showed a high ability of these ligands to chelate Cu-64(II) in very diluted medium. These new systems have the potential to be used for nuclear medicine and particularly for PET-imaging. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease
  作者：Fazal Rahim、Muhammad Tariq Javed、Hayat Ullah、Abdul Wadood、Muhammad Taha、Muhammad Ashraf、Qurat-ul-Ain、Muhammad Anas Khan、Fahad Khan、Salma Mirza、Khalid M. Khan

  DOI：10.1016/j.bioorg.2015.08.002

  日期：2015.10

  A series of thirty (30) thiazole analogs were prepared, characterized by H-1 NMR, C-13 NMR and EI-MS and evaluated for Acetylcholinesterase and butyrylcholinesterase inhibitory potential. All analogs exhibited varied butyrylcholinesterase inhibitory activity with IC50 value ranging between 1.59 +/- 0.01 and 389.25 +/- 1.75 mu M when compared with the standard eserine (IC50, 0.85 +/- 0.0001 mu M). Analogs 15, 7, 12, 9, 14, 1, 30 with IC50 values 1.59 +/- 0.01, 1.77 +/- 0.01, 6.21 +/- 0.01, 7.56 +/- 0.01, 8.46 +/- 0.01, 14.81 +/- 0.32 and 16.54 +/- 0.21 mu M respectively showed excellent inhibitory potential. Seven analogs 15, 20, 19, 24, 28, 30 and 25 exhibited good acetylcholinesterase inhibitory potential with IC50 values 21.3 +/- 0.50, 35.3 +/- 0.64, 36.6 +/- 0.70, 44.81 +/- 0.81, 46.36 +/- 0.84, 48.2 +/- 0.06 and 48.72 +/- 0.91 mu M respectively. All other analogs also exhibited well to moderate enzyme inhibition. The binding mode of these compounds was confirmed through molecular docking. (C) 2015 Elsevier Inc. All rights reserved.