1-methoxy-2,3-O-isopropylidene-5-deoxy-L-ribofuranose | 193526-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxy-2,3-O-isopropylidene-5-deoxy-L-ribofuranose
• 英文别名: Methyl 5-deoxy-2,3-O-isopropylidene-L-ribofuranoside；(3aS,6S,6aS)-4-methoxy-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 193526-83-9
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: RNHBZJGMAYMLBE-FKMOCYPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methoxy-2,3-O-isopropylidene-5-deoxy-L-ribofuranose 在 甲醇 、 硫酸 、 氨 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 反应 46.0h， 生成 1-((2S,3S,4R,5S)-3,4-Dihydroxy-5-methyl-tetrahydro-furan-2-yl)-1H-[1,2,4]triazole-3-carboxylic acid amide
  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-methoxy-2,3-O-isopropylidene-5-bromo-L-ribofuranose 在 10percent Pd/C 氢氧化钾 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到1-methoxy-2,3-O-isopropylidene-5-deoxy-L-ribofuranose
  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

• L-benzimidazole nucleosides
  申请人：Glaxo Wellcome Inc.

  公开号：US06204249B1

  公开（公告）日：2001-03-20

  The present invention relates to benzimidazole derivatives and their use in medical therapy particularly for the treatment or prophylaxis of virus infections such as those caused by herpes viruses. The invention also relates to the preparation of the benzimidazole derivatives and pharmaceutical formulations containing them.

  本发明涉及苯并咪唑衍生物及其在医学疗法中的应用，特别是用于治疗或预防病毒感染，如由疱疹病毒引起的感染。该发明还涉及苯并咪唑衍生物的制备以及含有它们的药物配方。
• US6204249B1
  申请人：——

  公开号：US6204249B1

  公开（公告）日：2001-03-20
• US6617315B1
  申请人：——

  公开号：US6617315B1

  公开（公告）日：2003-09-09