1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-O-disiloxanyl)-β-L-ribofuranosyl]-1,2,4-triazole-3-carboxamide | 263708-23-2

• 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: 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-O-disiloxanyl)-β-L-ribofuranosyl]-1,2,4-triazole-3-carboxamide
• 英文别名: 1-[(6aS,8S,9aR)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-1,2,4-triazole-3-carboxamide
• CAS: 263708-23-2
• 化学式: C₂₀H₃₈N₄O₅Si₂
• 分子量: 470.717
• InChiKey: BROATPLWSARHCT-SQNIBIBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-O-disiloxanyl)-β-L-ribofuranosyl]-1,2,4-triazole-3-carboxamide 在 triethylamine trihydrofluoride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以47%的产率得到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-3-carboxylate 在 吡啶 、 甲醇 、 偶氮二异丁腈 、 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 55.0h， 生成 1-[2-deoxy-3,5-O-(1,1,3,3-tetraisopropyl-1,3-O-disiloxanyl)-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

• Monocyclic <scp>l</scp>-Nucleosides with Type 1 Cytokine-Inducing Activity
  作者：Kanda S. Ramasamy、Robert C. Tam、Josie Bard、Devron R. Averett

  DOI：10.1021/jm9905514

  日期：2000.3.1

  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.