5-((5-(4-chlorophenyl)furan-2-yl)methylene)-3-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-oxoethyl)-2-thioxothiazolidin-4-one | 1160931-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-((5-(4-chlorophenyl)furan-2-yl)methylene)-3-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-oxoethyl)-2-thioxothiazolidin-4-one
• 英文别名: 5-[[5-(4-chlorophenyl)furan-2-yl]methylidene]-3-[2-[4-(2-fluorophenyl)piperazin-1-yl]-2-oxoethyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 1160931-83-8
• 化学式: C₂₆H₂₁ClFN₃O₃S₂
• 分子量: 542.054
• InChiKey: GNOGXFZMCKRMND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  36.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  57.0
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-羧甲基绕丹宁 在 N-甲基吗啉 、 sodium acetate 、 溶剂黄146 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 5-((5-(4-chlorophenyl)furan-2-yl)methylene)-3-(2-(4-(2-fluorophenyl)piperazin-1-yl)-2-oxoethyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Synthesis and in vivo anticancer and antiangiogenic effects of novel thioxothiazolidin-4-one derivatives against transplantable mouse tumor

  摘要：

  A series of novel thioxothiazolidin-4-one derivatives 5(a-g) were synthesized by the coupling of different amines containing aliphatic, substituted aromatic, and heterocyclic moieties, such as oxadiazol, pyrazole, isoxazole, and piperazine with 2-(5-(4-chlorophenyl)furan-2-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid. All compounds were characterized by H-1 NMR, LCMS, FTIR and elemental analysis. In this study, we investigated the possibility that these novel thioxothiazolidin-4-one derivatives 5(a-g) inhibits tumor growth and tumor induced angiogenesis using mouse Ehrlich Ascites Tumor (EAT) as a model system. Our results demonstrated that the compounds significantly reduced ascites tumor volume, cell number, and increased the life span of EAT-bearing mice. In addition, the compounds manifested strong antiangiogenic effects and suppressed tumor induced endothelial proliferation in the mice peritoneum. From our findings, it is noted that the derivatives 5(a-e) may be possible candidates for anticancer therapy with the ability to inhibit tumor angiogenesis and tumor cell proliferation.

  DOI：

  10.1007/s00044-009-9187-7