1-deaza-6-methyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine | 1193381-34-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deaza-6-methyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
• 英文别名: 7-methyl-3-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine
• CAS: 1193381-34-8
• 化学式: C₁₈H₂₁N₃O₇
• 分子量: 391.381
• InChiKey: DQSIIIULAVFTJO-GFOCRRMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  118.84
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-deaza-6-methyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine 在 氨 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到7-methyl-3-β-D-ribofuranosyl-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Synthesis of a 6-Methyl-7-deaza Analogue of Adenosine That Potently Inhibits Replication of Polio and Dengue Viruses

  摘要：

  Bioisosteric deaza analogues of 6-methyl-9-beta-D-ribofuranosylpurine, a hydrophobic analogue of adenosine, were synthesized and evaluated for antiviral activity. Whereas the 1-deaza and 3-deaza analogues were essentially inactive in plaque assays of infectivity, a novel 7-deaza-6-methyl-9-beta-D-ribofuranosylpurine analogue, structurally related to the natural product tubercidin, potently inhibited replication of poliovirus (PV) in HeLa cells (IC50 = 11 nM) and dengue virus (DENV) in Vero cells (IC50 = 62 nM). Selectivity against PV over cytotoxic effects to HeLa cells was > 100-fold after incubation for 7 h. Mechanistic studies of the 5'-triphosphate of 7-deaza-6-methyl-9-beta-D-riboluranosylpurine revealed that this compound is an efficient substrate of PV RNA-dependent RNA polymerase (RdRP) and is incorporated into RNA mimicking both ATP and GTP.

  DOI：

  10.1021/jm100593s
• 作为产物：
  描述：

  2-氨基-5-溴-4-甲基吡啶 在 盐酸 、 platinum(IV) oxide 、 硫酸 、 10% palladium on activated carbon 、 氢气 、 硝酸 、 对甲苯磺酸 、 tin(ll) chloride 、 sodium hydroxide 作用下， 以 水 为溶剂， -10.0~170.0 ℃ 、344.75 kPa 条件下， 反应 3.83h， 生成 1-deaza-6-methyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Synthesis of a 6-Methyl-7-deaza Analogue of Adenosine That Potently Inhibits Replication of Polio and Dengue Viruses

  摘要：

  Bioisosteric deaza analogues of 6-methyl-9-beta-D-ribofuranosylpurine, a hydrophobic analogue of adenosine, were synthesized and evaluated for antiviral activity. Whereas the 1-deaza and 3-deaza analogues were essentially inactive in plaque assays of infectivity, a novel 7-deaza-6-methyl-9-beta-D-ribofuranosylpurine analogue, structurally related to the natural product tubercidin, potently inhibited replication of poliovirus (PV) in HeLa cells (IC50 = 11 nM) and dengue virus (DENV) in Vero cells (IC50 = 62 nM). Selectivity against PV over cytotoxic effects to HeLa cells was > 100-fold after incubation for 7 h. Mechanistic studies of the 5'-triphosphate of 7-deaza-6-methyl-9-beta-D-riboluranosylpurine revealed that this compound is an efficient substrate of PV RNA-dependent RNA polymerase (RdRP) and is incorporated into RNA mimicking both ATP and GTP.

  DOI：

  10.1021/jm100593s