1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-benzylmercapto-6-azauracil | 172945-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-benzylmercapto-6-azauracil
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(6-benzylsulfanyl-3,5-dioxo-1,2,4-triazin-2-yl)oxan-2-yl]methyl acetate
• CAS: 172945-54-9
• 化学式: C₂₄H₂₈N₄O₁₀S
• 分子量: 564.573
• InChiKey: NWIPQDYLBCVDFR-MTSAVCEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  204
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-benzylmercapto-6-azauracil 在 甲醇 、 氨 作用下， 反应 18.0h， 以96%的产率得到1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-5-benzylmercapto-6-azauracil
  参考文献：
  名称：

  Synthesis and Biological Activity of Some 5-Substituted-6-azauracil-N-1-Nucleosides of 2-Acetamido-2-Deoxy-D-glucose

  摘要：

  Glycosylation of the silylated 5-bromo- and 5-benzylmercapto-6-azauracil 1 and 2, respectively, with the acylated sugar 3 afforded 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-5-br 4 and its 5-benzylmercapto analogue 6. Deblocking of 4 and 6 gave the free nucleosides 5 and 7, respectively. Alternatively, 6 was obtained from reaction of benzylmercaptan with 4 in pyridine. Reaction of 4 with morpholine, 2,4-dichlorobenzylamine and N-methylethanolamine gave the 5-alkylamino derivatives 8, 10 and 11, respectively. Deblocking of 8 gave nucleoside 9. All the newly synthesized compounds were characterized by their NMR, U.V. and mass specta. Compounds 5, 7, 9, 10 and 11 were tested for their activity against HIV type 1 and 2, but they did not show significant biological activity and not toxic at 100 mcg/ml. The antimutagenic activity of 5 and 7 is under investigation.

  DOI：

  10.1080/15257779508009750
• 作为产物：
  描述：

  5-benzylmercapto-6-azauracil 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 31.0h， 生成 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-5-benzylmercapto-6-azauracil
  参考文献：
  名称：

  Synthesis and Biological Activity of Some 5-Substituted-6-azauracil-N-1-Nucleosides of 2-Acetamido-2-Deoxy-D-glucose

  摘要：

  Glycosylation of the silylated 5-bromo- and 5-benzylmercapto-6-azauracil 1 and 2, respectively, with the acylated sugar 3 afforded 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-5-br 4 and its 5-benzylmercapto analogue 6. Deblocking of 4 and 6 gave the free nucleosides 5 and 7, respectively. Alternatively, 6 was obtained from reaction of benzylmercaptan with 4 in pyridine. Reaction of 4 with morpholine, 2,4-dichlorobenzylamine and N-methylethanolamine gave the 5-alkylamino derivatives 8, 10 and 11, respectively. Deblocking of 8 gave nucleoside 9. All the newly synthesized compounds were characterized by their NMR, U.V. and mass specta. Compounds 5, 7, 9, 10 and 11 were tested for their activity against HIV type 1 and 2, but they did not show significant biological activity and not toxic at 100 mcg/ml. The antimutagenic activity of 5 and 7 is under investigation.

  DOI：

  10.1080/15257779508009750