4-hydroxymethyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,3-triazole | 70964-84-0

• 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: 4-hydroxymethyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,3-triazole
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[4-(hydroxymethyl)triazol-1-yl]oxolan-2-yl]methyl acetate
• CAS: 70964-84-0
• 化学式: C₁₄H₁₉N₃O₈
• 分子量: 357.32
• InChiKey: OPPJBDZLQKHRBC-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-hydroxymethyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,3-triazole 在 盐酸 、 氨 、 原甲酸三乙酯 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 4-hydroxymethyl-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-1,2,3-triazole
  参考文献：
  名称：

  2,3,5-tri-O-acety]-β-D-ribofuranosyl azide and 2,3-O-isopropylidene-5-O-trityl-α-D-ribofuranosyl azide

  摘要：

  DOI：

  10.1016/s0008-6215(00)85377-x
• 作为产物：
  描述：

  四乙酰核糖 在 叠氮基三甲基硅烷 、 四氯化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.5h， 生成 4-hydroxymethyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,3-triazole
  参考文献：
  名称：

  2,3,5-tri-O-acety]-β-D-ribofuranosyl azide and 2,3-O-isopropylidene-5-O-trityl-α-D-ribofuranosyl azide

  摘要：

  DOI：

  10.1016/s0008-6215(00)85377-x

文献信息

• Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides
  作者：Khalid El Akri、Khalid Bougrin、Jan Balzarini、Abdesslem Faraj、Rachid Benhida

  DOI：10.1016/j.bmcl.2007.08.077

  日期：2007.12

  We report herein an efficient synthesis of 4-substituted triazolyl-nucleosides and their in vitro cytostatic activity. The synthesis is based on a straightforward 1,3-dipolar cycloaddition between 1-azido-ribose 2 and terminal alkynes under a cooperative effect of microwave activation and copper (I) catalysis. All cycloadducts were obtained in nearly quantitative yield after a short reaction time (1 to 2 min). After removal of acetyl protecting groups, the free nucleosides were evaluated against L1210, Molt4/C8, and CEM tumor cell lines. Structure - activity relationship study shows that the substituent on the triazole ring has a major effect since nucleosides 4c and 4g, containing, respectively, a long alkyl chain and an aryl donor group are the most active compounds in this series. (c) 2007 Elsevier Ltd. All rights reserved.
• 2,3,5-tri-O-acety]-β-D-ribofuranosyl azide and 2,3-O-isopropylidene-5-O-trityl-α-D-ribofuranosyl azide
  作者：Marìa José Camarasa、Rosario Alonso、Federico G. De las Heras

  DOI：10.1016/s0008-6215(00)85377-x

  日期：1980.8