5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide | 1146543-55-6

• 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: 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
• CAS: 1146543-55-6
• 化学式: C₁₄H₁₇IN₄O₈
• 分子量: 496.215
• InChiKey: DELYVFGSGALAIA-IDTAVKCVSA-N

物化性质

• 沸点：
  608.2±65.0 °C(predicted)
• 密度：
  2.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  161.93
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide 在 二(氰基苯)二氯化钯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.0h， 生成 1-(4-carbamoyl-5-ethynyl-[1,2,3]triazol-1-yl)-β-D-ribofuranose
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050
• 作为产物：
  描述：

  5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazole-4-carboxamide 在 二碘甲烷 、 亚硝酸异戊酯 作用下， 反应 1.5h， 以59%的产率得到5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
  参考文献：
  名称：

  5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties

  摘要：

  Efficient Pd(0)-catalysed synthesis of 5-alkynyl-1-beta-D-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide depends on the presence of different protecting groups of the ribose moiety. Peracetylated 5-iodo substrate (15) couples with terminal alkynes or trimethyl-[(tributylstannyl)ethynyl] silane in 50-71% and 72% yield (ETCAR), respectively, although its hydrodehalogenation to 19 is noticeable. On the other hand, hydrodehalogenation of acetonide (16) predominates over coupling with terminal alkyne and slightly decreases a yield of cross-coupling reaction with trimethyl[(tributylstannyl)ethynyl] silane. Alternative conditions of reaction with terminal alkynes, to exclude so far identified hydride sources to produce hydridopalladium species, have been established for acetonide 16 and allowed to achieve 72% of coupling. Fluoromethyl derivative (42) was prepared from its 5-hydroxymethyl precursor by fluorination with DAST. Additionally, X-ray structural analysis of 42 was performed. All 1,2,3-triazolonucleosides and two synthesized cycloSal-pronucleotides were evaluated for cytotoxic activity against K562, HeLa and HUVEC cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.050