3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide | 1232985-50-0

• 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: 3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
• 英文别名: 5-(3,4-dichlorophenyl)-3-(4-fluorophenyl)-3,4-dihydropyrazole-2-carbothioamide
• CAS: 1232985-50-0
• 化学式: C₁₆H₁₂Cl₂FN₃S
• 分子量: 368.262
• InChiKey: DHJGSIJZTMFTAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 、 溴乙酸 在 sodium acetate 、 溶剂黄146 、 乙酰氯 作用下， 以57%的产率得到2-(3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one
  参考文献：
  名称：

  Design, Synthesis, Characterization and In Silico Molecular Docking Studies and In Vivo Anti-inflammatory Activity of Pyrazoline Clubbed Thiazolinone Derivatives

  摘要：

  吡唑啉类化合物在其对高锰酸盐和新生氢的反应中表现出与不饱和化合物相似的行为，类似于脂肪衍生物。这种核与各种生物活性有关，包括炎症作用。噻唑酮是一种含有硫和氮原子以及羰基的杂环化合物。由于其多种生物活性，如抗炎、抗微生物、抗增殖、抗病毒、抗抽搐等，噻唑酮及其衍生物一直受到持续关注。研究的目的是将吡唑啉核与噻唑酮结合，以获得显著的抗炎活性。合成的化合物在化学上被表征以确定其化学结构，并评估其作为抗炎药物的效果。 在本研究中，通过三步反应合成了八种取代吡唑啉衍生物（PT1-PT8）。这些化合物经过红外、质谱和核磁共振光谱以及元素分析数据的光谱分析。所有合成的衍生物均评估了它们的体内抗炎活性。通过使用吲哚美辛作为参考化合物，评估了合成衍生物对COX-1和COX-2的亲和力，通过AutoDock Vina进行分子对接可视化。 化合物PT-1、PT-3、PT-4和PT-8在第3小时表现出显著的抗炎活性，分别为50.7%、54.3%、52.3%和57%，接近标准药物吲哚美辛（61.9%）的效果。从选定的抗炎靶点来看，合成的衍生物与COX-1和COX-2受体的相互作用更好，吲哚美辛的对接分数为-6.5 kJ/mol，化合物PT-1在COX-1上表现出最高的对接分数为-9.1 kJ/mol，而化合物PT-8在COX-2上的对接分数为9.4 kJ/mol。 结论是合成的衍生物与COX-2受体的相互作用比与COX-1受体的相互作用更多，因为与COX-2受体的对接分数非常好。可以得出结论，合成的衍生物（PT-1至PT-8）是有效的COX-2抑制剂。

  DOI：

  10.2174/1570178617999201106113114
• 作为产物：
  描述：

  1-(3,4-Dichlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(3,4-dichlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors

  摘要：

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.021

文献信息

• Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors
  作者：Ke-Ming Qiu、Ru Yan、Man Xing、Hai-Hong Wang、Hong-En Cui、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.09.021

  日期：2012.11

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.
• Design, Synthesis, Characterization and In Silico Molecular Docking Studies and In Vivo Anti-inflammatory Activity of Pyrazoline Clubbed Thiazolinone Derivatives
  作者：Deepak Kumar Singh、Mayank Kulshreshtha、Yogesh Kumar、Pooja A. Chawla、Akash Ved、Karuna Shanker Shukla

  DOI：10.2174/1570178617999201106113114

  日期：2021.7.29