2-(3-(4-chlorophenyl)-1H-pyrazol-4-yl)-3-(3-mercapto-5-(o-tolyloxymethyl)-4H-1,2,4-triazol-4-yl)thiazolidin-4-one | 1378893-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-(4-chlorophenyl)-1H-pyrazol-4-yl)-3-(3-mercapto-5-(o-tolyloxymethyl)-4H-1,2,4-triazol-4-yl)thiazolidin-4-one
• 英文别名: 2-[5-(4-chlorophenyl)-1H-pyrazol-4-yl]-3-[3-[(2-methylphenoxy)methyl]-5-sulfanylidene-1H-1,2,4-triazol-4-yl]-1,3-thiazolidin-4-one
• CAS: 1378893-41-4
• 化学式: C₂₂H₁₉ClN₆O₂S₂
• 分子量: 499.017
• InChiKey: DYRUWWYIHKGRLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(((3-(4-chlorophenyl)-1H-pyrazol-4-yl)methylene)amino)-5-((o-tolyloxy)methyl)-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73%的产率得到2-(3-(4-chlorophenyl)-1H-pyrazol-4-yl)-3-(3-mercapto-5-(o-tolyloxymethyl)-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