4-[4-chlorobenzylidenamino]-5-phenyl-4H-1,2,4-triazol-3-thiol | 160465-44-1

• 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-chlorobenzylidenamino]-5-phenyl-4H-1,2,4-triazol-3-thiol
• 英文别名: 4-((4-chlorobenzylidene)amino)-5-phenyl-4H-1,2,4-triazole-3-thiol；4-{[(4-Chlorophenyl)methylidene]amino}-5-phenyl-2,4-dihydro-3h-1,2,4-triazole-3-thione；4-[(4-chlorophenyl)methylideneamino]-3-phenyl-1H-1,2,4-triazole-5-thione
• CAS: 160465-44-1
• 化学式: C₁₅H₁₁ClN₄S
• 分子量: 314.798
• InChiKey: QKKLUASVVJOQNW-UHFFFAOYSA-N

物化性质

• 熔点：
  209 °C
• 沸点：
  431.7±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 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：
  72.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[4-chlorobenzylidenamino]-5-phenyl-4H-1,2,4-triazol-3-thiol 在 三乙胺 作用下， 以 氘代二甲亚砜 、 乙醇 为溶剂， 反应 0.5h， 生成 cis-7-benzoyl-6-p-chlorophenyl-3-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine
  参考文献：
  名称：

  二氢噻二嗪和二氢噻二唑的立体选择性合成及其热解脱硫环的收缩

  摘要：

  分子内碱催化的C–C键形成导致反式-6,7-dihydro-5 H- [1,2,4]三唑[3,4- b ] [1,3,4]噻二嗪，反式的排他立体选择性合成-7,8-二氢-6- ħ - [1,2,4]三嗪并[3,4- b ] [1,3,4]噻二嗪-4-酮，和反式-3,4-二氢2 ħ - [1,3,4] thiadiazino [2,3 - b ] quinazolin-10-one。反式-6,7-二氢-5- ħ - [1,2,4]三唑并[3,4- b ] [1,3,4]噻二嗪在CDCl慢慢异构化3和更迅速地在DMSO- d 6为相应的顺式立体异构体。另一个反式-6,7-二氢-[1,3,4]噻二嗪在DMSO- d 6中也异构化为相应的顺式立体异构体。这些杂环缩合的二氢噻二嗪热解转化为其相应的吡唑并[5,1- b ] [1,2,4]三唑，吡唑并[5,1- c ] [1,2,4]三嗪-4-酮和吡唑并[描述了通过脱硫环收缩的4，3

  DOI：

  10.1016/j.tet.2011.06.034
• 作为产物：
  描述：

  potassium 3-benzoyldithiocarbazinate 在 溶剂黄146 、 肼 作用下， 生成 4-[4-chlorobenzylidenamino]-5-phenyl-4H-1,2,4-triazol-3-thiol
  参考文献：
  名称：

  Impact of Inclusion Complex Formation on Absorption and Emission Characteristics of Some 4-Arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols

  摘要：

  一系列4-芳基亚胺基-5-苯基-4H-1,2,4-三氮唑-3-硫醇的包合物与β-环糊精合成。通过研究它们的物理和光谱性质，对这些化合物及其包合物进行了表征。为了解包合物的稳定性及主客体关系的类型，确定了热力学稳定常数和活化自由能。最后，使用吸收、激发和发射光谱来检查包合物形成是否对4-芳基亚胺基-5-苯基-4H-1,2,4-三氮唑-3-硫醇的吸收和发射特性产生影响。结果发现，包合物的形成导致新合成化合物的吸收、激发和发射光谱发生了剧烈变化。

  DOI：

  10.14233/ajchem.2016.19556

文献信息

• Synthesis, biological activities and SAR studies of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases as ketol-acid reductoisomerase inhibitors
  作者：Bao-Lei Wang、Li-Yuan Zhang、Xing-Hai Liu、Yi Ma、Yan Zhang、Zheng-Ming Li、Xiao Zhang

  DOI：10.1016/j.bmcl.2017.10.065

  日期：2017.12

  A series of new 3-substitutedphenyl-4-substitutedbenzylideneamino-1,2,4-triazole Mannich bases and bis-Mannich bases were synthesized through Mannich reaction with high yields. Their structures were confirmed by means of IR, 1H NMR, 13C NMR and elemental analysis. The preliminary bioassay indicated that compounds 7g, 7h and 7l exhibited potent in vitro inhibitory activities against ketol-acid reductoisomerase

  通过Mannich反应合成了一系列新的3-取代苯基-4-取代的亚苄基氨基-1,2,4-三唑曼尼希碱和双曼尼希碱。通过IR，1 H NMR，13 C NMR和元素分析证实了它们的结构。初步的生物测定结果表明，化合物7g，7h和7l对K i的酮醇酸还原异构酶（KARI）表现出有效的体外抑制活性。值分别为（0.38±0.25），（6.59±2.75）和（8.46±3.99）μmol/ L，与IpOHA相当。它们可能是用于后续研究的新型KARI抑制剂。一些标题化合物还表现出对明显的除草活性稗草和显着的体外杀真菌活性针对轮纹轮纹病菌和纹枯病菌。分析了化合物的SAR，其中分子对接揭示了7g与KARI的结合模式，并且3D-QSAR结果为指导进一步优化这种结构以发现针对谷物纹枯病的新型杀真菌剂提供了有用的信息。
• 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。
• 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.
• Impact of Inclusion Complex Formation on Absorption and Emission Characteristics of Some 4-Arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
  作者：Sunakar Panda、Sashikanta Nayak、P.K. Das、D.L. Singh

  DOI：10.14233/ajchem.2016.19556

  日期：——

  The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesized with b-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 relation. Finally, the absorption, excitation and emission spectra of the compounds and their inclusion complexes have been taken to examine whether the inclusion complex formation has any impact on absoption and emission characteristics of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols. It is found that inclusion complex formation brings about a drastic change in absorption, excitation and emission spectra of newly synthesized compounds.

  一系列4-芳基亚胺基-5-苯基-4H-1,2,4-三氮唑-3-硫醇的包合物与β-环糊精合成。通过研究它们的物理和光谱性质，对这些化合物及其包合物进行了表征。为了解包合物的稳定性及主客体关系的类型，确定了热力学稳定常数和活化自由能。最后，使用吸收、激发和发射光谱来检查包合物形成是否对4-芳基亚胺基-5-苯基-4H-1,2,4-三氮唑-3-硫醇的吸收和发射特性产生影响。结果发现，包合物的形成导致新合成化合物的吸收、激发和发射光谱发生了剧烈变化。
• Stereoselective synthesis of dihydrothiadiazinoazines and dihydrothiadiazinoazoles and their pyrolytic desulfurization ring contraction
  作者：Alya Al-Etaibi、Elizabeth John、Maher R. Ibrahim、Nouria A. Al-Awadi、Yehia A. Ibrahim

  DOI：10.1016/j.tet.2011.06.034

  日期：2011.8

  4]thiadiazines isomerize also in DMSO-d6 into the corresponding cis-stereoisomers. Pyrolytic conversion of these heterocyclic condensed dihydrothiadiazines into their corresponding pyrazolo[5,1-b][1,2,4]triazoles, pyrazolo[5,1-c][1,2,4]triazin-4-ones and pyrazolo[4,3-b]quinazolin-9-ones via desulfurization ring contraction is described.

  分子内碱催化的C–C键形成导致反式-6,7-dihydro-5 H- [1,2,4]三唑[3,4- b ] [1,3,4]噻二嗪，反式的排他立体选择性合成-7,8-二氢-6- ħ - [1,2,4]三嗪并[3,4- b ] [1,3,4]噻二嗪-4-酮，和反式-3,4-二氢2 ħ - [1,3,4] thiadiazino [2,3 - b ] quinazolin-10-one。反式-6,7-二氢-5- ħ - [1,2,4]三唑并[3,4- b ] [1,3,4]噻二嗪在CDCl慢慢异构化3和更迅速地在DMSO- d 6为相应的顺式立体异构体。另一个反式-6,7-二氢-[1,3,4]噻二嗪在DMSO- d 6中也异构化为相应的顺式立体异构体。这些杂环缩合的二氢噻二嗪热解转化为其相应的吡唑并[5,1- b ] [1,2,4]三唑，吡唑并[5,1- c ] [1,2,4]三嗪-4-酮和吡唑并[描述了通过脱硫环收缩的4，3