8-amino-6-(4-methylbenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one | 858780-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 8-amino-6-(4-methylbenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one
• CAS: 858780-44-6
• 化学式: C₁₂H₁₂N₆OS
• 分子量: 288.333
• InChiKey: SNWZSQILYVEWTD-UHFFFAOYSA-N

物化性质

• 熔点：
  223 °C(Solv: N,N-dimethylformamide (68-12-2); acetic acid (64-19-7))
• 沸点：
  431.8±48.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.0
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  吡啶 、 8-amino-6-(4-methylbenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 三乙胺 作用下， 以69%的产率得到8-amino-6-(4-methylbenzyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one pyridinium salt
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663
• 作为产物：
  描述：

  4-amino-6-(4-methylbenzyl)-3-thioxo-2,3-dihydro-1,2,4-triazin-5(4H)-one 在 吡啶 、 sodium methylate 、 一水合肼 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 6.0h， 生成 8-amino-6-(4-methylbenzyl)-2,8-dihydro-3-thioxo-1,2,4-triazolo[4,3-b][1,2,4]-triazin-7(3H)-one
  参考文献：
  名称：

  Synthesis of Some Novel 6‐Benzyl(or Substituted Benzyl)‐2‐β‐d‐Glucopyranosyl‐1,2,4‐Triazolo[4,3‐b][1,2,4]Triazines as Potential Antimicrobial Chemotherapeutics

  摘要：

  Glucosidation of the new 8-amino-6-benzyl(or substituted benzyl)-2,8-dihydro-1,2,4tri azolo [4,3-b] [1,2,4]triazin-7(3 H)-ones (3a-d) with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide 4 gave the corresponding N-glucosides 5a-d. Chemical transformations leading to new functionalities have also been achieved to give compounds 7-12. Antimicrobial activity of compounds 5a-c against Aspergillus fumigatus, Penicillium italicum, Syncephalastrum racemosum, Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis, Escherichia coli is described.

  DOI：

  10.1081/ncn-200040663