4-[(furan-2-yl)methyleneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol

• 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-[(furan-2-yl)methyleneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-[(Furan-2-ylmethylidene)amino]-5-phenyl-2,4-dihydro-3h-1,2,4-triazole-3-thione；4-(furan-2-ylmethylideneamino)-3-phenyl-1H-1,2,4-triazole-5-thione
• 化学式: C₁₃H₁₀N₄OS
• 分子量: 270.315
• InChiKey: DRVAQVMLKHKTRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(furan-2-yl)methyleneamino]-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-(furan-2-yl)-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：

  苯甲酸甲酯 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 4-[(furan-2-yl)methyleneamino]-5-phenyl-4H-1,2,4-triazole-3-thiol
  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

文献信息

• Novel Triazole-Piperazine Hybrid Molecules Induce Apoptosis <i>via</i> Activation of the Mitochondrial Pathway and Exhibit Antitumor Efficacy in Osteosarcoma Xenograft Nude Mice Model
  作者：Chandra Bhushan Mishra、Raj Kumar Mongre、Shikha Kumari、Dong Kee Jeong、Manisha Tiwari

  DOI：10.1021/acschembio.6b01007

  日期：2017.3.17

  of a novel series of triazole-piperazine hybrids as potent anticancer agents. MCS-5 emerged as an excellent anticancer agent which showed better anticancer activity than the standard drug doxorubicin in in vitro and in vivo studies. MCS-5 displayed an IC50 value of 1.92 μM and induced apoptosis in Cal72 (human osteosarcoma cell line) cells by targeting the mitochondrial pathway. This compound arrested

  线粒体除了作为主要能源外，在调节程序性细胞死亡和活性氧（ROS）产生的过程中也起着至关重要的作用。线粒体由于其对细胞存活和死亡的显着贡献，似乎已成为治疗癌症的重要靶标。在这里，我们报告设计和合成的新型三唑-哌嗪杂种作为有效的抗癌药。MCS-5是一种出色的抗癌药，在体外和体内研究中显示出比标准药物阿霉素更好的抗癌活性。MCS-5显示了IC 50靶向线粒体途径后，Cal72（人骨肉瘤细胞系）细胞的凋亡值达到1.92μM，并诱导其凋亡。该化合物阻止了细胞周期的G2 / M期，并在Cal72细胞中诱导了ROS的产生和线粒体电位的崩溃。MCS-5在Cal72异种移植裸鼠模型中显示出优异的抗癌活性，与对照和阿霉素治疗的动物相比，MCS-5显着降低了肿瘤的进展，从而延长了治疗动物的寿命，而没有产生明显的毒性。此外，一项2DG光学探针指导的研究清楚地表明，MCS-5显着降低了Cal72异种移植裸鼠模型中的
• 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。
• Antibacterial, antioxidant and anthelmintic studies of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
  作者：Sunakar Panda、Sashikanta Nayak

  DOI：10.1080/10610278.2015.1075533

  日期：2015.10.3

  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.
• Sengupta, S. K.; Kumar, Shyam, Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1982, vol. 12, p. 287 - 296
  作者：Sengupta, S. K.、Kumar, Shyam

  DOI：——

  日期：——