1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-amino-1H-[1,2,3]triazole-4-carboxylic acid amide | 1321591-86-9

• 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-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-amino-1H-[1,2,3]triazole-4-carboxylic acid amide
• 英文别名: 5-amino-4-carboxamide-1,2,3-triazole nucleoside
• CAS: 1321591-86-9
• 化学式: C₁₃H₁₉N₅O₆
• 分子量: 341.324
• InChiKey: UXCCXDHDHPTGNO-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.06
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  153.81
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-amino-1H-[1,2,3]triazole-4-carboxylic acid amide 在 叔丁基过氧化氢 、 二(氰基苯)二氯化钯 、 二碘甲烷 、 sodium methylate 、 potassium carbonate 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 甲醇 、 癸烷 、 乙腈 为溶剂， 反应 2.33h， 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：

  2,3-O-isopropylidene-β-D-ribofuranosyl-1-azide 在 吡啶 、 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-amino-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

文献信息

• 2-Aryl-8-aza-3-deazaadenosine analogues of 5′-O-[N-(salicyl)sulfamoyl]adenosine: Nucleoside antibiotics that block siderophore biosynthesis in Mycobacterium tuberculosis
  作者：Anna Krajczyk、Joanna Zeidler、Piotr Januszczyk、Surendra Dawadi、Helena I. Boshoff、Clifton E. Barry、Tomasz Ostrowski、Courtney C. Aldrich

  DOI：10.1016/j.bmc.2016.05.037

  日期：2016.7

  A series of 5′-O-[N-(salicyl)sulfamoyl]-2-aryl-8-aza-3-deazaadenosines were designed to block mycobactin biosynthesis in Mycobacterium tuberculosis (Mtb) through inhibition of the essential adenylating enzyme MbtA. The synthesis of the 2-aryl-8-aza-3-deazaadenosine nucleosides featured sequential copper-free palladium-catalyzed Sonogashira coupling of a precursor 4-cyano-5-iodo-1,2,3-triazolonucleoside

  设计了一系列5'- O- [ N-（水杨酰基）氨磺酰基] -2-芳基-8-氮杂-3-脱氮杂腺苷，通过抑制必需的腺苷酸化酶MbtA来阻断结核分枝杆菌（Mtb）中分支杆菌素的生物合成。2-芳基-8-氮杂-3-脱氮杂氨基腺苷核苷的合成特征在于前体4-氰基-5-碘-1,2,3-三唑代核苷与末端炔烃和Minakawa的连续无铜钯催化的Sonogashira偶联–松田环化反应。这些修饰的核苷显示抑制MbtA的表观K i值为6.1至25 nM，并抑制Mtb。 在缺铁条件下生长，抑制最小浓度范围为12.5至> 50μM。