3-((5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazol-2-ylthio)methyl)-4H-chromen-4-one | 1449385-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-((5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazol-2-ylthio)methyl)-4H-chromen-4-one
• 英文别名: 3-[[5-[(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanylmethyl]-1,3,4-thiadiazol-2-yl]sulfanylmethyl]chromen-4-one；3-[[5-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanylmethyl]-1,3,4-thiadiazol-2-yl]sulfanylmethyl]chromen-4-one
• CAS: 1449385-49-2
• 化学式: C₂₀H₁₆N₆O₂S₃
• 分子量: 468.584
• InChiKey: CAVHXQRFYVHKND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  174
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazole-2-thiol 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺-d7 、 水 为溶剂， 以89%的产率得到3-((5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-1,3,4-thiadiazol-2-ylthio)methyl)-4H-chromen-4-one
  参考文献：
  名称：

  Efficient synthesis and antiproliferative activity of novel thioether-substituted flavonoids

  摘要：

  As widely occurring natural products, flavonoids are an important source for drug discovery, due to their structural diversity and broad-spectrum biological activity. In this work, a library of novel, thioether-substituted flavonoids with diverse heterocyclic groups was synthesized via a microwave-assisted procedure with the advantages of good yields, short times, mild conditions and ready isolation of the products. Their antiproliferative activities were evaluated against six cancer cell lines, HCCLM-7, Hela, MDA-MB-435S, SW-480, Hep-2, and MCF-7 by the MU-based assay. Compared with the positive control 5-fluorouracil, three compounds, 6a, 6b and 6j were successfully identified as the most promising candidates, due to their higher potency and broad-spectrum bioactivity with IC50 values in the range of 0.43 mu M-6.7 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.037