methyl (2,3-di-O-acetyl-5-deoxy-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate | 263708-37-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3-di-O-acetyl-5-deoxy-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate
• 英文别名: methyl 1-[(2S,3S,4S,5S)-3,4-diacetyloxy-5-methyloxolan-2-yl]-1,2,4-triazole-3-carboxylate
• CAS: 263708-37-8
• 化学式: C₁₃H₁₇N₃O₇
• 分子量: 327.294
• InChiKey: BGKCZXGRSRNDII-RBHNIQJYSA-N

物化性质

• 沸点：
  462.6±55.0 °C(predicted)
• 密度：
  1.49±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (2,3-di-O-acetyl-5-deoxy-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate 在 甲醇 、 氨 作用下， 反应 18.0h， 以72%的产率得到1-((2S,3S,4R,5S)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carboxylic acid amide
  参考文献：
  名称：

  Monocyclic l-Nucleosides with Type 1 Cytokine-Inducing Activity

  摘要：

  A series of 1,2,4-triazole L-nucleosides were synthesized and evaluated for their ability to stimulate type 1 cytokine production by activated human T cells in direct comparison to the known active agent ribavirin. Among the compounds prepared, 1-beta-L-ribofuranosyl-1,2,4-triazole-3-carboxamide (5, ICN 17261) was found to be the most uniformly potent compound. Conversion of the 3-carboxamide group of 5 to a carboxamidine functionality resulted in 1-beta-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride(10), which induced cytokine levels comparable to 5 for two of the three type 1 cytokines examined. Modification of the carbohydrate moiety of 5 provided compounds of reduced activity. Significantly, ICN 17261 offers interesting immunomodulatory potential for the treatment of diseases where type 1 cytokines play an important role.

  DOI：

  10.1021/jm9905514
• 作为产物：
  描述：

  1-methoxy-2,3-O-isopropylidene-5-bromo-L-ribofuranose 在 10percent Pd/C 氢氧化钾 、 硫酸 、 氢气 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 40.0h， 生成 methyl (2,3-di-O-acetyl-5-deoxy-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Monocyclic l-Nucleosides with Type 1 Cytokine-Inducing Activity

  摘要：

  A series of 1,2,4-triazole L-nucleosides were synthesized and evaluated for their ability to stimulate type 1 cytokine production by activated human T cells in direct comparison to the known active agent ribavirin. Among the compounds prepared, 1-beta-L-ribofuranosyl-1,2,4-triazole-3-carboxamide (5, ICN 17261) was found to be the most uniformly potent compound. Conversion of the 3-carboxamide group of 5 to a carboxamidine functionality resulted in 1-beta-ribofuranosyl-1,2,4-triazole-3-carboxamidine hydrochloride(10), which induced cytokine levels comparable to 5 for two of the three type 1 cytokines examined. Modification of the carbohydrate moiety of 5 provided compounds of reduced activity. Significantly, ICN 17261 offers interesting immunomodulatory potential for the treatment of diseases where type 1 cytokines play an important role.

  DOI：

  10.1021/jm9905514