4-amino-3-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,2,4-triazol-5-thiol | 494200-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 4-amino-3-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,2,4-triazol-5-thiol
• 英文别名: 4-amino-5-{[(5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanyl]methyl}-4H-1,2,4-triazol-3-yl hydrosulfide；4-amino-3-[(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfanylmethyl]-1H-1,2,4-triazole-5-thione
• CAS: 494200-05-4
• 化学式: C₁₀H₁₂N₈S₂
• 分子量: 308.391
• InChiKey: DNJPBZRCFWPMFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-3-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,2,4-triazol-5-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91%的产率得到2-((4-amino-5-((5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylthio)methyl)-4H-1,2,4-triazol-3-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
• 作为产物：
  描述：

  2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,3,4-oxadiazol-5-thiol 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以27%的产率得到4-amino-3-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine-2-thiomethyl)-1,2,4-triazol-5-thiol
  参考文献：
  名称：

  基于 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]-嘧啶的二杂环化合物的合成。

  摘要：

  描述了由 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶 (1) 合成一些二杂环化合物。化合物 1 可以转化为三唑、1,3,4-恶二唑和 1,3,4-噻二唑。中间体和目标化合物的结构经(1)H-NMR、MS和元素分析确证。

  DOI：

  10.3390/molecules13061353

文献信息

• Efficient synthesis and antiproliferative activity of novel thioether-substituted flavonoids
  作者：Wei Huang、Qiong Chen、Wen-Chao Yang、Guang-Fu Yang

  DOI：10.1016/j.ejmech.2013.05.037

  日期：2013.8

  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.
• Syntheses of Diheterocyclic Compounds Based on 2-Thioacetohydrazide-5,7-dimethyl-1,2,4-triazolo[1,5-a]- pyrimidine
  作者：Zu-Ming Liu、Qiong Chen、Chao-Nan Chen、Hai-Yang Tu、Guang-Fu Yang

  DOI：10.3390/molecules13061353

  日期：——

  The syntheses of some diheterocyclic compounds from 2-thioacetohydrazide- 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine (1) are described. Compound 1 can be converted into triazoles, 1,3,4-oxadiazoles, and 1,3,4-thiadiazoles. The structures of the intermediates and the target compounds were confirmed by (1)H-NMR, MS and elemental analyses.

  描述了由 2-硫代乙酰肼-5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶 (1) 合成一些二杂环化合物。化合物 1 可以转化为三唑、1,3,4-恶二唑和 1,3,4-噻二唑。中间体和目标化合物的结构经(1)H-NMR、MS和元素分析确证。