1-thiocarbamoyl-3-(3',4'-dimethylphenyl)-5-phenyl-2-pyrazoline | 296795-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-thiocarbamoyl-3-(3',4'-dimethylphenyl)-5-phenyl-2-pyrazoline
• 英文别名: 5-(3,4-Dimethylphenyl)-3-phenyl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 296795-10-3
• 化学式: C₁₈H₁₉N₃S
• 分子量: 309.435
• InChiKey: HAQJISXHNJSRLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙酸 、 1-thiocarbamoyl-3-(3',4'-dimethylphenyl)-5-phenyl-2-pyrazoline 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以64%的产率得到2-[5-(3,4-Dimethylphenyl)-3-phenyl-3,4-dihydropyrazol-2-yl]-1,3-thiazol-4-one
  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
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1-thiocarbamoyl-3-(3',4'-dimethylphenyl)-5-phenyl-2-pyrazoline
  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 of some thiazolyl-pyrazoline derivatives and preliminary investigation of their hypotensive activity
  作者：G Turan-Zitouni

  DOI：10.1016/s0223-5234(00)00152-5

  日期：2000.6

  Some 1-(4-arylthiazol-2-yl)-3,5-diaryl-2-pyrazoline derivatives were synthesized by reacting 1-thiocarbamoyl-3,5-diaryl-2-pyrazoline derivatives with phenacetylbromide in ethanol. The structural elucidation of the compounds were performed by IR, 1H-NMR and Mass spectral data and elemental analyses. The hypotensive activities of 13 compounds were evaluated by using the tail-cuff method. All examined

  通过使1-硫代氨基甲酰基-3,5-二芳基-2-吡唑啉衍生物与苯乙酰溴在乙醇中反应，合成了一些1-（4-芳基噻唑-2-基）-3,5-二芳基-2-吡唑啉衍生物。通过IR，1 H-NMR和质谱数据以及元素分析进行​​化合物的结构阐明。使用尾套法评估了13种化合物的降压活性。所有检查的化合物均显示出明显的降压活性。可乐定在药理评估中用作参考物质。