1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide | 263708-17-4

• 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-carboxamide
• 英文别名: acetic acid 3S,4S-bis-acetoxy-5S-(3-carbamoyl-[1,2,4]triazol-1-yl)-tetrahydro-furan-2S-ylmethyl ester；1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxamide；[(2S,3S,4S,5S)-3,4-diacetyloxy-5-(3-carbamoyl-1,2,4-triazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 263708-17-4
• 化学式: C₁₄H₁₈N₄O₈
• 分子量: 370.319
• InChiKey: XVXXBJKZJDPHAU-RMIALFOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  162
• 氢给体数：
  1
• 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-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
• 作为产物：
  描述：

  methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate 在 吡啶 、 甲醇 、 氨 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-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

文献信息

• METHOD FOR PRODUCING FURANOSE DERIVATIVE
  申请人：Katsurada Manabu

  公开号：US20100105890A1

  公开（公告）日：2010-04-29

  An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl- 1 -O-alkyl-ribofuranose and 2,3-di-O-acyl- 1 -O-alkyl-5-deoxy-ribofuranose.

  本发明的目的是提供一种工业上适用的方法，以高选择性和高产率生产核黄素糖苷衍生物的β-异构体。本发明提供了一种生产核黄素糖苷衍生物的方法，其中通过控制反应试剂的用量和/或使用劣质溶剂，在2,3,5-三-O-酰基-1-O-烷基-核黄素糖苷和2,3-二-O-酰基-1-O-烷基-5-去氧-核黄素糖苷的乙酰化反应中沉淀β-异构体。
• Method for producing furanose derivative
  申请人：Katsurada Manabu

  公开号：US08394935B2

  公开（公告）日：2013-03-12

  An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.

  本发明的目的是提供一种在高产率和高选择性的情况下生产核黄素衍生物β异构体的工业适用方法。本发明提供了一种生产核黄素衍生物的方法，其中通过控制反应试剂的用量和/或在2,3,5-三-O-酰基-1-O-烷基-核糖呋喃和2,3-二-O-酰基-1-O-烷基-5-去氧-核糖呋喃的醋酸解反应中使用劣溶剂，从生成的呋喃糖衍生物中沉淀β异构体。
• METHOD FOR PRODUCTION OF FURANOSE DERIVATIVE
  申请人：API Corporation

  公开号：EP2105445A1

  公开（公告）日：2009-09-30

  An object of the present invention is to provide a industrially appropriate method for producing the β-anomers of ribofuranose derivatives in a highly selective manner at a high yield. The present invention provides a method for producing ribofuranose derivatives wherein β-anomers is precipitated from among the generated furanose derivatives by controlling the amount of a reaction reagent used and/or using a poor solvent in the acetolysis reactions of 2,3,5-tri-O-acyl-1-O-alkyl-ribofuranose and 2,3-di-O-acyl-1-O-alkyl-5-deoxy-ribofuranose.

  本发明的目的是提供一种以高选择性和高产率的方式生产核呋喃糖衍生物β-异构体的工业化适当方法。本发明提供了一种生产核呋喃糖衍生物的方法，通过控制 2,3,5-三-O-酰基-1-O-烷基核呋喃糖和 2,3-二-O-酰基-1-O-烷基-5-脱氧核呋喃糖乙酰分解反应中反应试剂的用量和/或使用贫溶剂，从生成的呋喃糖衍生物中析出 β-异构体。
• US8394935B2
  申请人：——

  公开号：US8394935B2

  公开（公告）日：2013-03-12