4-(((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)amino)-5-(phenoxymethyl)-4H-1,2,4-triazole-3-thiol | 1258254-19-1

• 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-(((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)amino)-5-(phenoxymethyl)-4H-1,2,4-triazole-3-thiol
• CAS: 1258254-19-1
• 化学式: C₁₉H₁₅FN₆OS
• 分子量: 394.432
• InChiKey: VPSGNZBIVJYDGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.88
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-(((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)amino)-5-(phenoxymethyl)-4H-1,2,4-triazole-3-thiol 、 巯基乙酸 在 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以67%的产率得到2-(3-(4-fluorophenyl)-1H-pyrazol-4-yl)-3-(3-mercapto-5-(phenoxymethyl)-4H-1,2,4-triazol-4-yl)thiazolidin-4-one
  参考文献：
  名称：

  Synthesis, characterization, anticancer, and antioxidant activity of some new thiazolidin-4-ones in MCF-7 cells

  摘要：

  There are limited studies centring on the potential of thiazolidin-4-ones as anticancer agents. In this study, a new series of 2-(3-substituted-1H-pyrazol-4-yl)-3-(3-substituted-5-sulfanyl-1,2,4-triazol-4-yl)-1,3-thiazolidin-4-one (4a-o) have been synthesized by cyclo-condensation reaction of 5-substituted-4-[(3-substituted-1H-pyrazol-4-ylmethylidene)amino]-2H-1,2,4-triazole-3-thione (3a-o) and thioglycolic acid. The structures of all the synthesized compounds were confirmed by elemental analysis, spectral techniques like IR, H-1 NMR, and mass spectroscopy. Few compounds exhibited dose-dependent cytotoxic effect in MTT assay in human breast cancer (MCF-7) cells. Apoptotic degradation of DNA due to action of potent thiazolidin-4-ones was analysed by agarose gel electrophoresis and visualized by ethidium bromide staining (comet assay). A concentration-dependent increase in tail length and olive tail moment was observed when treated with thiazolidin-4-ones. In vitro antioxidant studies like DPPH and ABTS-free radical scavenging assays-indicated moderate activity of thiazolidin-4-ones.

  DOI：

  10.1007/s00044-012-0071-5
• 作为产物：
  描述：

  3-(4-氟苯基)-1H-吡唑-4-甲醛 、 2,4-二氢-4-氨基-5-(苯氧基甲基)-3H-噻唑-3-三酮 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 4-(((3-(4-fluorophenyl)-1H-pyrazol-4-yl)methylene)amino)-5-(phenoxymethyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis, characterization, anticancer, and antioxidant activity of some new thiazolidin-4-ones in MCF-7 cells

  摘要：

  There are limited studies centring on the potential of thiazolidin-4-ones as anticancer agents. In this study, a new series of 2-(3-substituted-1H-pyrazol-4-yl)-3-(3-substituted-5-sulfanyl-1,2,4-triazol-4-yl)-1,3-thiazolidin-4-one (4a-o) have been synthesized by cyclo-condensation reaction of 5-substituted-4-[(3-substituted-1H-pyrazol-4-ylmethylidene)amino]-2H-1,2,4-triazole-3-thione (3a-o) and thioglycolic acid. The structures of all the synthesized compounds were confirmed by elemental analysis, spectral techniques like IR, H-1 NMR, and mass spectroscopy. Few compounds exhibited dose-dependent cytotoxic effect in MTT assay in human breast cancer (MCF-7) cells. Apoptotic degradation of DNA due to action of potent thiazolidin-4-ones was analysed by agarose gel electrophoresis and visualized by ethidium bromide staining (comet assay). A concentration-dependent increase in tail length and olive tail moment was observed when treated with thiazolidin-4-ones. In vitro antioxidant studies like DPPH and ABTS-free radical scavenging assays-indicated moderate activity of thiazolidin-4-ones.

  DOI：

  10.1007/s00044-012-0071-5

文献信息

• Synthesis, characterization and in vitro cytotoxic properties of some new Schiff and Mannich bases in Hep G2 cells
  作者：Dhanya Sunil、Arun M. Isloor、Prakash Shetty、B. Chandrakantha、K. Satyamoorthy

  DOI：10.1007/s00044-010-9433-z

  日期：2011.9

  Schiff bases, 3a, 3d, 3e, 3g and 3h showed dose dependent cytotoxic activity, 3a being the most potent with an IC50 value of 0.018 g/l comparable to the standard drug doxorubicin. Among the Mannich bases, 5b was the most active with an IC50 value of 0.034 g/l. The Schiff bases were found to be more active, when compared to Mannich bases derived from them. The morpholine derived Mannich bases were more

  合成了一系列的5-取代的4-氨基-3-巯基-1,2,4-三唑，并用各种3-取代的吡唑醛进行处理，以获得一系列新的席夫碱（3a – l）。在乙醇介质中（4a – e，5a – e），在甲醛存在下，通过与二苯胺/吗啉反应，很少有选定的席夫碱转化为曼尼希碱。这些新合成的化合物通过元素分析，IR，NMR和质谱研究进行了表征。使用MTT分析法对HepG2细胞中几种选定的Schiff和Mannich碱基的细胞毒性活性进行了比较研究。很少有经过筛选的希夫碱3a，3d，3e，3g和3h表现出剂量依赖性的细胞毒性活性，与标准药物阿霉素相比，3a最有效，IC 50值为0.018 g / l。在曼尼希碱中，5b活性最高，IC 50值为0.034 g / l。与衍生自其的曼尼希碱相比，席夫碱的活性更高。吗啉衍生的曼尼希碱比从二苯胺获得的碱更有效。