1-methoxy-2,3-O-isopropylidene-5-bromo-L-ribofuranose | 263708-34-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxy-2,3-O-isopropylidene-5-bromo-L-ribofuranose
• 英文别名: (3aS,6R,6aR)-6-(bromomethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 263708-34-5
• 化学式: C₉H₁₅BrO₄
• 分子量: 267.12
• InChiKey: WAABJMSNMPZCDB-FKMOCYPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、310.27 kPa 条件下， 反应 24.0h， 生成 1,2,3-tri-O-acetyl-5-deoxy-L-ribofuranose
  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：

  L-呋喃核糖 在 盐酸 、 溴 、 三苯基膦 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 1-methoxy-2,3-O-isopropylidene-5-bromo-L-ribofuranose
  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