methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate | 263708-15-2

• 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: methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate
• 英文别名: Methyl-1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate；methyl 2-[(2S,3S,4S,5S)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate
• CAS: 263708-15-2
• 化学式: C₁₅H₁₉N₃O₉
• 分子量: 385.331
• InChiKey: HEOMJLCCXYSIGI-MNXVOIDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate 在 甲醇 、 氨 作用下， 反应 18.0h， 以77%的产率得到2-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
  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 、 双(对硝基苯基)磷酸酯 作用下， 以 甲醇 为溶剂， 反应 41.42h， 生成 methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-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

文献信息

• Treatment of viral infections using the L-isomer of ribavirin
  申请人：——

  公开号：US06518253B1

  公开（公告）日：2003-02-11

  A 1-(&bgr;-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide is administered in a method of treatment of a viral infection in a patient, including HIV infection, HCV infection, or BHV infection.

  在治疗患者的病毒感染，包括HIV感染，HCV感染或BHV感染的方法中，给予1-（&bgr; -L-核糖呋喃基）-1,2,4-三唑-3-羧酰胺。
• Treatment of viral infections using levovirin
  申请人：——

  公开号：US20030092644A1

  公开（公告）日：2003-05-15

  A 1-(&bgr;-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide is administered in a method of treatment of a viral infection in a patient, including IV infection, HCV infection, or BHV infection.

  一种1-(&bgr;-L-核糖呋喃基)-1,2,4-三唑-3-羧酰胺在治疗患有病毒感染的患者中使用，包括静脉感染、丙型肝炎感染或牛瘤病毒感染。
• US6518253B1
  申请人：——

  公开号：US6518253B1

  公开（公告）日：2003-02-11