(+/-)-5-amino-1-(2-hydroxy-4-hydroxymethylcyclopentyl)-1H-[1,2,3]triazole-4-carboxylic acid amide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-5-amino-1-(2-hydroxy-4-hydroxymethylcyclopentyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
• 英文别名: 5-amino-1-[(1R,2R,4S)-2-hydroxy-4-(hydroxymethyl)cyclopentyl]triazole-4-carboxamide
• 化学式: C₉H₁₅N₅O₃
• 分子量: 241.25
• InChiKey: UFAJARQKHRXLPQ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-5-amino-1-(2-hydroxy-4-hydroxymethylcyclopentyl)-1H-[1,2,3]triazole-4-carboxylic acid amide 在 二(氰基苯)二氯化钯 吡啶 、 二碘甲烷 、 sodium methylate 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成 (+/-)-1-(2-hydroxy-4-hydroxymethylcyclopentyl)-6-(4-pentylphenyl)-1,5-dihydro-[1,2,3]triazolo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  Efficient Pd(0)-catalyzed synthesis of 1,2,3-triazolo-3′-deoxycarbanucleosides and their analogues

  摘要：

  The racemic synthesis of hitherto unknown 5-substituted-[1,2,3]-triazolo-3'-deoxycarbanucleosides and [1,2,3]-triazolo-[4,5-c] pyridin-4-one analogues is described. The key iodinated intermediate 10 was prepared in 10 steps using a malonic synthesis. Various alkynes were introduced at the C-5 position of 10 under optimized Pd(0)-catalyzed Sonogashira cross-coupling alkyrylation to yield after deprotection 12a-i. The synthesis of their 8-aza-3-deazapurine analogues (13a-h) was also accomplished through the heteroannulation of internal alkynes under aqueous dimethylamine. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.034
• 作为产物：
  描述：

  anti-3-(Hydroxymethyl)-6-oxabicyclo<3.1.0>hexane 在 sodium azide 、 potassium carbonate 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 (+/-)-5-amino-1-(2-hydroxy-4-hydroxymethylcyclopentyl)-1H-[1,2,3]triazole-4-carboxylic acid amide
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolo-carbanucleoside analogues of ribavirin targeting an HCV in replicon

  摘要：

  The synthesis of carbocyclic and phosphonocarbocyclic analogues of ribavirin, an anti-HCV inhibitor, are described. Those compounds were evaluated against HCV but also against other important viruses in order to determine their spectrum of antiviral activity. Compounds 6 and 13 displayed a moderate IC50 against HIV-1 of 43.8 and 37 muM, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00349-3