1-(2'-3'-O-isopropylidene-β-D-ribofuranosyl)-4-carbamoyl-5-amino-3H-1,2,3-triazole | 143722-82-1

• 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'-O-isopropylidene-β-D-ribofuranosyl)-4-carbamoyl-5-amino-3H-1,2,3-triazole
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-aminotriazole-4-carboxamide
• CAS: 143722-82-1
• 化学式: C₁₁H₁₇N₅O₅
• 分子量: 299.286
• InChiKey: WNARIXCYDZMBBX-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2'-3'-O-isopropylidene-β-D-ribofuranosyl)-4-carbamoyl-5-amino-3H-1,2,3-triazole 在 吡啶 、 叔丁基过氧化氢 、 二(氰基苯)二氯化钯 、 二碘甲烷 、 sodium methylate 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 甲醇 、 癸烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.33h， 生成 1-(5-O-((saligenin-α,2-di-O-yl)phosphoryl)-2,3-O-isopropylidene-β-D-ribofuranosyl)-1H-[1,2,3]triazole-4-carboxamide
  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：

  β-D-Ribofuranosylazid 在 乙醇 、 Dowex H⁺ 、 sodium 作用下， 以 丙酮 为溶剂， 反应 25.0h， 生成 1-(2'-3'-O-isopropylidene-β-D-ribofuranosyl)-4-carbamoyl-5-amino-3H-1,2,3-triazole
  参考文献：
  名称：

  Biagi; Giorgi; Livi, Il Farmaco, 1992, vol. 47, # 5, p. 525 - 536

  摘要：

  DOI：

文献信息

• NEW INHIBITORS OF PLATELET AGGREGATION
  申请人：AstraZeneca AB

  公开号：EP0840740B1

  公开（公告）日：2002-05-02
• Biagi; Giorgi; Livi, Il Farmaco, 1992, vol. 47, # 5, p. 525 - 536
  作者：Biagi、Giorgi、Livi、Scartoni

  DOI：——

  日期：——
• 5-Ethynyl-1-β-d-ribofuranosyl-1H-[1,2,3]triazole-4-carboxylic acid amide (ETCAR) and its analogues: Synthesis and cytotoxic properties
  作者：Tomasz Ostrowski、Piotr Januszczyk、Marcin Cieslak、Julia Kazmierczak-Baranska、Barbara Nawrot、Elzbieta Bartoszak-Adamska、Joanna Zeidler

  DOI：10.1016/j.bmc.2011.05.050

  日期：2011.7

  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.