methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate | 206269-26-3

• 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-3-carboxylate
• 英文别名: Methyl-1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate；methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate；methyl 1-[(2S,3S,4S,5S)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxylate
• CAS: 206269-26-3
• 化学式: C₁₅H₁₉N₃O₉
• 分子量: 385.331
• InChiKey: OLQDKJGHMNCLOH-MNXVOIDGSA-N

物化性质

• 沸点：
  521.5±60.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

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-3-carboxylate 在 吡啶 、 甲醇 、 偶氮二异丁腈 、 triethylamine trihydrofluoride 、 二苯基硅烷 、 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 1-[(2S,4R,5S)-4-hydroxy-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：

  methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-5-carboxylate 生成 methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Treatment of viral infections using the L-isomer of ribavirin

  摘要：

  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。

  公开号：

  US06518253B1

文献信息

• Monocyclic L-Nucleosides, analogs and uses thereof
  申请人：ICN Pharmaceuticals, Inc.

  公开号：US06130326A1

  公开（公告）日：2000-10-10

  Novel monocyclic L-Nucleoside compounds have the general formula ##STR1## Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.

  新型单环L-核苷化合物的一般公式为##STR1##。这些化合物的实施形式被认为在治疗各种疾病方面是有用的，包括感染、寄生虫感染、肿瘤和自身免疫性疾病。从机制上看，这些新型化合物的实施形式显示出免疫调节活性，并有望在调节细胞因子模式方面发挥作用，包括调节Th1和Th2反应。
• Monocyclic L-nucleosides, analogs and uses thereof
  申请人：ICN Pharmaceuticals, Inc.

  公开号：EP1254911A1

  公开（公告）日：2002-11-06

  Novel monocyclic L- nucleoside compounds have general formula (I). Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th 1 and Th 2 response.

  新型单环L-核苷化合物的一般化学式为（I）。这些化合物的实施形式被认为在治疗包括感染、寄生虫感染、肿瘤和自身免疫性疾病在内的各种疾病中是有用的。从机制上看，这些新型化合物的实施形式显示出免疫调节活性，并有望在调节细胞因子模式方面发挥作用，包括调节Th1和Th2反应。
• Process for producing a ribofuranose
  申请人：——

  公开号：US20040034213A1

  公开（公告）日：2004-02-19

  A method of converting pure &agr;-anomer or &bgr;/&agr;-anomer mixtures of 1,2,3,5-tetra-O-acetyl-L-ribofuranose to methyl-1-(2,3,5 -tri-O-acetyl-&bgr;-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate an intermediate for levovirin, as well as, the novel pure &agr;-anomer, alpha 1,2,3,5-tetra-O-acetyl-L-ribofuiranose, are useful in manufacturing levovirin.

  一种将纯的α-异构体或1,2,3,5-四-O-乙酰-L-核糖呋喃糖的β/α-异构体混合物转化为甲基-1-(2,3,5-三-O-乙酰-β-L-核糖呋喃糖基)-1,2,4-三唑-3-羧酸酯的方法，这是左环病毒素的中间体，以及新颖的纯α-异构体，α-1,2,3,5-四-O-乙酰-L-核糖呋喃糖，对于制造左环病毒素很有用。
• 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。
• Moncyclic L-nucleosides analogs
  申请人：ICN Pharmaceuticals, Inc.

  公开号：US06552183B1

  公开（公告）日：2003-04-22

  Novel monocyclic L-Nucleoside compounds have the general formula Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.

  新型单环L-核苷化合物的通式为 。这些化合物的实施形式被认为在治疗各种疾病，包括感染、寄生虫感染、肿瘤和自身免疫性疾病方面有用。从机理上看，这些新化合物的实施形式显示出免疫调节活性，并且预计在调节细胞因子模式方面有用，包括调节Th1和Th2反应。