4-methoxy-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine | 270065-08-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 4-methoxy-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-methoxyimidazo[4,5-d]triazin-7-yl)oxolan-2-yl]methyl acetate
• CAS: 270065-08-2
• 化学式: C₁₆H₁₉N₅O₈
• 分子量: 409.356
• InChiKey: KZSBTFLBTAFFFY-XNIJJKJLSA-N

物化性质

• 沸点：
  588.0±60.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-methoxy-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine 在 sodium carbonate 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 9.0h， 生成 4-hydrazino-7-(β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine
  参考文献：
  名称：

  Synthesis of 4-Substituted Imidazo[4,5-d][1,2,3]triazine (2-Azapurine)nucleosides

  摘要：

  Several methods for functionalization of the 4-position of imidazo[4,5-d][1,2,3]triazin-4-one were investigated. These investigations were successful and led to the preparation of 4-amino, 4-triazol-1-yl, 4-methoxy, 4-methylthio, 4-methylamino, 4-thio, 4-nitrobenzyl, and 4-unsubstituted 9-(beta-D-ribofuranosyl)-imidazo-[4,5-d][1,2,3]triazine (2-azapurine ribosides). The 4-unsubstituted compound (19) was slightly active against HCMV in plaque and yield reduction experiments and was not cytotoxic at 100 mu M. The methylamino (15), hydrazino (16), and p-nitrobenzylthio (20) were inactive against HCMV but slightly cytotoxic. The thiomethyl-substituted analog (21) was the most active with activity comparable to ganciclovir but with greater cytotoxicity. We conclude that even though none of the tested compounds had antiviral activity superior to ganciclovir, the new synthetic methods will provide a route to more interesting compounds.

  DOI：

  10.1080/15257770008032996
• 作为产物：
  描述：

  甲醇 、 2',3',5'-tri-O-(acetyl)-2-azainosine 在 4-二甲氨基吡啶 、 三氯氧磷 、 氨 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以27%的产率得到4-methoxy-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine
  参考文献：
  名称：

  Synthesis of 4-Substituted Imidazo[4,5-d][1,2,3]triazine (2-Azapurine)nucleosides

  摘要：

  Several methods for functionalization of the 4-position of imidazo[4,5-d][1,2,3]triazin-4-one were investigated. These investigations were successful and led to the preparation of 4-amino, 4-triazol-1-yl, 4-methoxy, 4-methylthio, 4-methylamino, 4-thio, 4-nitrobenzyl, and 4-unsubstituted 9-(beta-D-ribofuranosyl)-imidazo-[4,5-d][1,2,3]triazine (2-azapurine ribosides). The 4-unsubstituted compound (19) was slightly active against HCMV in plaque and yield reduction experiments and was not cytotoxic at 100 mu M. The methylamino (15), hydrazino (16), and p-nitrobenzylthio (20) were inactive against HCMV but slightly cytotoxic. The thiomethyl-substituted analog (21) was the most active with activity comparable to ganciclovir but with greater cytotoxicity. We conclude that even though none of the tested compounds had antiviral activity superior to ganciclovir, the new synthetic methods will provide a route to more interesting compounds.

  DOI：

  10.1080/15257770008032996