2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-4-amino-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione | 1021323-44-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-4-amino-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione
• CAS: 1021323-44-3
• 化学式: C₁₈H₂₁N₅O₇S
• 分子量: 451.46
• InChiKey: XJYISGKQBBLUTI-LJIGWXMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  149.79
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2-(2,3,4-tri-O-acetyl-α-L-arabinopyranosyl)-4-amino-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione 在 氨 作用下， 以 甲醇 为溶剂， 以92%的产率得到2-α-L-arabinopyranosyl-4-amino-5-(pyridin-3-yl)-2,4-dihydro-[1,2,4]-triazole-3-thione
  参考文献：
  名称：

  First Synthesis And Antimicrobial Activity OfN- andS-α-L-Arabinopyranosyl-1,2,4-Triazoles

  摘要：

  Arabinosylation of some 4-amino- and4-arylideneamino-5-(pyridin- 3- yl)-2,4 dihydro- 1,2,4]triazole- 3- thiones with 2,3,4-tri-O-acetyl-beta-L-arabinopyranosyl bromide led to an efficient synthetic approach to the corresponding N- and S-alpha-L-arabinopyranosides. Structure assignment of these two regiosiomers was based on chemical and spectroscopic evidences. Antimicrobial activities of two selected regioisomeric N- and S-alpha-L-arabinopyranosides were compared. The N-alpha-L-arabinopyranoside showed higher inhibitory effect than its regioisomeric S-alpha-L-arabinopyranoside against Aspergillus fumigatus, Penicillium italicum, Staphylococcus aureus, and Pseudomonas aeruginosa.

  DOI：

  10.1080/15257770701296986
• 作为产物：
  描述：

  4-氨基-5-吡啶-4H-[1,2,4]噻唑-3-硫醇 、 三乙酰基-β-L-溴代阿拉伯糖 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到3-(2,3,4-tri-O-acetyl-α-L-arabinopyranosylthio)-4-amino-5-(pyridin-3-yl)-4H-[1,2,4]-triazole
  参考文献：
  名称：

  First Synthesis And Antimicrobial Activity OfN- andS-α-L-Arabinopyranosyl-1,2,4-Triazoles

  摘要：

  Arabinosylation of some 4-amino- and4-arylideneamino-5-(pyridin- 3- yl)-2,4 dihydro- 1,2,4]triazole- 3- thiones with 2,3,4-tri-O-acetyl-beta-L-arabinopyranosyl bromide led to an efficient synthetic approach to the corresponding N- and S-alpha-L-arabinopyranosides. Structure assignment of these two regiosiomers was based on chemical and spectroscopic evidences. Antimicrobial activities of two selected regioisomeric N- and S-alpha-L-arabinopyranosides were compared. The N-alpha-L-arabinopyranoside showed higher inhibitory effect than its regioisomeric S-alpha-L-arabinopyranoside against Aspergillus fumigatus, Penicillium italicum, Staphylococcus aureus, and Pseudomonas aeruginosa.

  DOI：

  10.1080/15257770701296986