1-((2-chloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide | 104827-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-((2-chloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide
• 英文别名: 1-[(2-chloroquinolin-3-yl)methylideneamino]-3-(2-methylphenyl)thiourea
• CAS: 104827-39-6
• 化学式: C₁₈H₁₅ClN₄S
• 分子量: 354.863
• InChiKey: SHWDMGDHVDMTSH-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  515.6±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.31
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-((2-chloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide 、 乙酸酐 以64%的产率得到N-(4-acetyl-5-(2-chloroquinolin-3-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)-N-o-tolylacetamide
  参考文献：
  名称：

  3-(1,3,4-Thiadiazole-2-yl)quinoline derivatives: Synthesis, characterization and anti-microbial activity

  摘要：

  A new series of thiadiazoles and intermediate thiosemicarbazones were synthesized from the chloroquinone molecule, with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection. The chemical structures of the compound were elucidated by elemental analysis, FTIR, 1H and 13C NMR and ESI-MS spectral data. In vitro anti-microbial activity was performed against Staphylococcus aureus, Streptococcus pyogenes, Salmonella typhimurium, and Escherichia coli. The MIC was detected using the double dilution method. The results were compared by calculating percent inhibit area/mu g of the compounds and the standard "amoxicillin". The selected compounds were tested for cytotoxic results using MIT assay H9c2 cardiac myoblasts cell line and the results showed that all the compounds offered remarkable >80% viability to a concentration of 200 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.013
• 作为产物：
  描述：

  邻甲苯胺 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 1-((2-chloroquinolin-3-yl)methylene)-4-o-tolylthiosemicarbazide
  参考文献：
  名称：

  3-(1,3,4-Thiadiazole-2-yl)quinoline derivatives: Synthesis, characterization and anti-microbial activity

  摘要：

  A new series of thiadiazoles and intermediate thiosemicarbazones were synthesized from the chloroquinone molecule, with an aim to explore their effect on in vitro growth of microorganisms causing microbial infection. The chemical structures of the compound were elucidated by elemental analysis, FTIR, 1H and 13C NMR and ESI-MS spectral data. In vitro anti-microbial activity was performed against Staphylococcus aureus, Streptococcus pyogenes, Salmonella typhimurium, and Escherichia coli. The MIC was detected using the double dilution method. The results were compared by calculating percent inhibit area/mu g of the compounds and the standard "amoxicillin". The selected compounds were tested for cytotoxic results using MIT assay H9c2 cardiac myoblasts cell line and the results showed that all the compounds offered remarkable >80% viability to a concentration of 200 mu g/mL. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.013

文献信息

• Pristine 2-chloroquinoline-based-thiosemicarbazones as multitarget agents against alzheimer's disease: In vitro and in silico studies of monoamine oxidase (MAO) and cholinesterase (ChE) inhibitors
  作者：Saquib Jalil、Rabia Basri、Mubashir Aziz、Zahid Shafiq、Syeda Abida Ejaz、Abdul Hameed、Jamshed Iqbal

  DOI：10.1016/j.molstruc.2024.137841

  日期：2024.6

  Neurodegenerative diseases can be treated more effectively with multitarget approaches. monoamine oxidases (MAOs) acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) are promising agents for cognitive decline. Here, a series of novel 2-chloroquinoline-3-carbaldehyd thiosemicarbazone derivatives ( were synthesized via a single-pot reaction. testing results showed four compound and having chloro

  通过多靶点方法可以更有效地治疗神经退行性疾病。单胺氧化酶（MAO）、乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）是治疗认知能力下降的有希望的药物。在此，通过单锅反应合成了一系列新型2-氯喹啉-3-缩醛缩氨基硫脲衍生物。测试结果表明，四种具有氯、氟、甲基和乙基官能团的化合物对MAO-A、MAO表现出高效能-B、AChE 和 BChE，IC 值分别为 0.549 ± 0.045、0.340 ± 0.02、0.280 ± 0.135 和 2.77 ± 0.62 µM。化合物对所有四种目标酶均表现出最大的抑制潜力。采用密度泛函理论 (DFT) 计算评估有效衍生物的反应曲线。我们发现化合物 、 和 表现出很强的反应活性，因为它们的 LUMO/HOMO 能隙很窄。此外，分子对接研究显示出优异的对接分数，配体很好地容纳在目标活性位点中分子动力学（MD）模拟证实了蛋白质-配体复合物的稳定性，该模拟揭