4-[4-methoxybenzylideneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol | 258855-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[4-methoxybenzylideneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-[(4-methoxyphenyl)methylideneamino]-3-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 258855-61-7
• 化学式: C₁₆H₁₄N₄OS
• 分子量: 310.379
• InChiKey: BXIQSSYWDJBGQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[4-methoxybenzylideneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol 在 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 26.0h， 生成 (E)-1-(4-methoxyphenyl)-N-[3-({[1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl]methyl}thio)-5-phenyl-4H-1,2,4-triazol-4-yl]methanimine
  参考文献：
  名称：

  Synthesis and Evaluation of Antioxidant, Antibacterial, and Target Protein-Molecular Docking of Novel 5-Phenyl-2,4-dihydro-3H-1,2,4-triazole Derivatives Hybridized with 1,2,3-Triazole via the Flexible SCH2-Bonding

  摘要：

  DOI：

  10.1134/s1070363220120300
• 作为产物：
  描述：

  potassium 3-benzoyldithiocarbazinate 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.17h， 生成 4-[4-methoxybenzylideneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Antibacterial, antioxidant and anthelmintic studies of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols

  摘要：

  A series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesised and their inclusion complexes have been prepared with -cyclodextrin. The compounds and their inclusion complexes have been characterised by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes. Finally, the compounds and their inclusion complexes are screened for antibacterial, antioxidant and anthelmintic activities. It is found that inclusion complexes of the newly synthesised compounds have appreciable stability and inclusion complex formation increases the antibacterial, antioxidant and anthelmintic activities significantly as compared to naked compound.

  DOI：

  10.1080/10610278.2015.1075533

文献信息

• Studies on Absorption and Emission Characteristics of Inclusion Complexes of Some 4-Arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols
  作者：Sunakar Panda、Sashikanta Nayak

  DOI：10.1007/s10895-015-1728-5

  日期：2016.3

  The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1, 2, 4-triazole-3-thiols have been prepared with β-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes and type of host-guest

  用β-环糊精制备了一系列4-芳基氨基-5-苯基-4H-1、2、4-三唑-3-硫醇的包合物。通过研究它们的物理和光谱特性，可以对化合物及其包合物进行表征。确定了热力学稳定性常数和活化自由能，以了解包合物的稳定性和主体-客体关系的类型。最后，对化合物（4-芳基氨基-5-苯基-4H-1、2，4-三唑-3-硫醇）及其包合物的吸收，激发和发射光谱进行了测定。发现包合物的形成引起新合成的化合物的吸收和荧光特性（激发和发射光谱）都发生急剧变化。
• On the possibility for synthesizing dihydrotriazolothiadiazoles by condensation of 4-amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones with aromatic aldehydes
  作者：A. Ya. Bespalov、T. L. Gorchakova、A. Yu. Ivanov、M. A. Kuznetsov、L. M. Kuznetsova、A. S. Pankova、L. I. Prokopenko、A. F. Khlebnikov

  DOI：10.1134/s1070428016030210

  日期：2016.3

  Regardless of the conditions, the condensation of 4-amino-2,4-dihydro-3H-1,2,4-triazole-3-thiones with aromatic aldehydes afforded the corresponding hydrazones as the only product. Both initial amines and resulting hydrazones exist as the thione rather than thiol tautomer. In no case bicyclic 5,6-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles that are isomeric to the hydrazones were detected. DFT

  无论条件如何，4-氨基-2,4-二氢-3 H -1,2,4-三唑-3-硫酮与芳族醛的缩合得到相应的为唯一产物。初始胺和生成的均以硫酮而不是硫醇互变异构体的形式存在。在任何情况下均未检测到与酮异构体的双环5,6-二氢[1,2,4]三唑并[3,4- b ] [1,3,4]噻二唑。B3LYP / 6-31 + g（d，p的DFT量子化学计算））具有完整几何优化的理论水平表明，甲醇和DMF中的structure结构比双环异构体稳定19-23 kcal / mol，这完全排除了这种环化的可能性。的硫酮互变异构体比硫醇结构稳定11-13 kcal / mol。
• Sireesha, Aliya B.; Reddy, Ch. Venkata Ramana; Devi, Ch. Sarala, Journal of the Indian Chemical Society, 2008, vol. 85, # 9, p. 926 - 929
  作者：Sireesha, Aliya B.、Reddy, Ch. Venkata Ramana、Devi, Ch. Sarala

  DOI：——

  日期：——
• Thiosemicarbazone fragment embedded within 1,2,4-triazole ring as inhibitors of Entamoeba histolytica
  作者：Shadab Miyan Siddiqui、Attar Salahuddin、Amir Azam

  DOI：10.1016/j.bmcl.2012.02.084

  日期：2012.4

  A series of 1,2,4-triazole derivatives containing thiosemicarbazone linkage was synthesized and evaluated for their in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. All the compounds were capable of inhibiting the growth of E. histolytica out of which four compounds (IC50 = 0.28-1.38 mu M) were found to have better efficacy than the standard drug Metronidazole (IC50 = 1.8 mu M). Cytotoxicity of the active compounds was assessed by MTT assay using human breast cancer MCF-7 cell line, which revealed that all the compounds were low cytotoxic in the concentration range of 2.5-250 mu M. (C) 2012 Elsevier Ltd. All rights reserved.