1-[(4′-chlorophenyl)carbonyl-4-(4″-chlorophenyl)]thiosemicarbazide | 31409-10-6

• 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: 1-[(4′-chlorophenyl)carbonyl-4-(4″-chlorophenyl)]thiosemicarbazide
• 英文别名: 1-<4-Chlor-benzoyl>-4-<4-Chlor-phenyl>-thiosemicarbazid；1-[(4-Chlorobenzoyl)amino]-3-(4-chlorophenyl)thiourea
• CAS: 31409-10-6
• 化学式: C₁₄H₁₁Cl₂N₃OS
• 分子量: 340.233
• InChiKey: YMKNOSCQKXVNFG-UHFFFAOYSA-N

物化性质

• 密度：
  1.470±0.06 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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4′-chlorophenyl)carbonyl-4-(4″-chlorophenyl)]thiosemicarbazide 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 4,5-bis(4-chlorophenyl)-3-methylthio-1H-1,2,4-triazole
  参考文献：
  名称：

  Preparation and antiarthritic activity of new 1,5-diaryl-3-alkylthio-1H-1,2,4-triazoles and corresponding sulfoxides and sulfones

  摘要：

  DOI：

  10.1016/0223-5234(90)90015-u
• 作为产物：
  描述：

  4-氯苯甲酸苯酯 在 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.5h， 生成 1-[(4′-chlorophenyl)carbonyl-4-(4″-chlorophenyl)]thiosemicarbazide
  参考文献：
  名称：

  1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation

  摘要：

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.

  DOI：

  10.1021/jm0495632

文献信息

• 1-[(4′-Chlorophenyl) carbonyl-4-(aryl) thiosemicarbazide derivatives as potent urease inhibitors: Synthesis, in vitro and in silico studies
  作者：Basharat Ali、Khalid Mohammed Khan、Uzma Salar、Kanwal、Safdar Hussain、Muhammad Ashraf、Muhammad Riaz、Abdul Wadood、Muhammad Taha、Shahnaz Perveen

  DOI：10.1016/j.bioorg.2018.05.017

  日期：2018.9

  compared to the standard thiourea (IC50 = 21.25 ± 0.13 μM). Amongst the potent analogs, compounds 3 (IC50 = 2.31 ± 0.01 μM), 6 (IC50 = 2.14 ± 0.04 μM), 10 (IC50 = 1.14 ± 0.06 μM), 20 (IC50 = 2.15 ± 0.05 μM), and 25 (IC50 = 0.32 ± 0.01 μM) are many folds more active than the standard. Structure-activity relationship (SAR) was rationalized by looking at the effect of diversely substituted aryl ring on inhibitory

  合成了一系列1-[（（4'-氯苯基）羰基-4-（芳基）硫代氨基脲] 1 – 25，并通过光谱技术（例如EI-MS和1 H NMR）进行了表征。 与标准硫脲（IC 50  = 21.25± 0.13μM）相比，所有化合物的体外尿素酶抑制活性均得到筛选，并在IC 50 = 0.32±0.01–25.13±0.13μM范围内表现出优异的抑制活性。在有效的类似物中，化合物3（IC 50  = 2.31±0.01μM），6（IC 50  = 2.14±0.04μM），10（IC 50  = 1.14±0.06μM），20（IC50  = 2.15±0.05μM）和25（IC 50  = 0.32±0.01μM）的活性比标准品高很多倍。通过考察不同取代的芳基环对抑制电位的影响来合理化结构-活性关系（SAR），该效应预测，不管取代基的性质如何，它们在芳基环上的位置对于有效活性都很重要。此外，为验证这些解
• Synthesis, Molecular Docking and Evaluation of Library of 3-Mercapto-1,2,4-Triazole Derivatives as Antimicrobial Agents
  作者：Swarnagowri Nayak、Santosh L. Gaonkar、Sushruta S. Hakkimane、Swapna B、Nitinkumar S. Shetty

  DOI：10.14233/ajchem.2021.23472

  日期：——

  Due to the increasing microbial resistance to antibacterial and antifungal drugs, the development of new antimicrobial agents is an urgent priority. In search of newer antimicrobial agents, a series of 4,5-disubstituted-3-mercapto-1,2,4-triazole derivatives were synthesized from aromatic acids and substituted isothiocyanates. The in silico study was performed to study the binding interactions of the synthesized compounds with the active pocket of CYP51. Among the synthesized 3-mercapto-triazole derivatives, compounds 6r, 6s and 6u exhibited promising antimicrobial activity comparable to standard drugs. The results suggested that the structural modification to 3-mercapto-1,2,4-triazole derivatives could lead to promising antimicrobial scaffolds.

  由于细菌对抗菌药物和抗真菌药物的耐药性不断增加，开发新的抗微生物药物成为当务之急。在寻找新型抗微生物药物的过程中，从芳香酸和取代异硫氰酸酯合成了一系列4,5-二取代-3-巯基-1,2,4-三唑衍生物。进行了体外研究以研究合成化合物与CYP51活性口袋的结合相互作用。在合成的3-巯基-三唑衍生物中，化合物6r、6s和6u表现出与标准药物可比的有前景的抗微生物活性。结果表明，对3-巯基-1,2,4-三唑衍生物进行结构修饰可以产生有前景的抗微生物骨架。
• 1,3,4-Thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure−Antituberculosis Activity Relationship Investigation
  作者：Elçin E. Oruç、Sevim Rollas、Fatma Kandemirli、Nathaly Shvets、Anatholy S. Dimoglo

  DOI：10.1021/jm0495632

  日期：2004.12.1

  A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl)-1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.
• Preparation and antiarthritic activity of new 1,5-diaryl-3-alkylthio-1H-1,2,4-triazoles and corresponding sulfoxides and sulfones
  作者：G SZILAGYI

  DOI：10.1016/0223-5234(90)90015-u

  日期：1990.3