1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carbonitrile | 263708-18-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 三唑核糖核苷和核糖核苷酸
• 英文名称: 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carbonitrile
• 英文别名: [(2S,3S,4S,5S)-3,4-diacetyloxy-5-(3-cyano-1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 263708-18-5
• 化学式: C₁₄H₁₆N₄O₇
• 分子量: 352.304
• InChiKey: IXMTWJNGXZIMAL-PYJNHQTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carbonitrile 在 甲醇 、 氨 、 sodium methylate 、 氯化铵 作用下， 生成 [amino-[1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazol-3-yl]methylidene]azanium;chloride
  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-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide 在 吡啶 、 光气 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以73%的产率得到1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carbonitrile
  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