5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamidoadenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamidoadenosine
• 英文别名: [(3aR,4R,6S,6aS)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-(aziridin-1-yl)methanone
• 化学式: C₁₅H₁₈N₆O₄
• 分子量: 346.346
• InChiKey: XFKGEIMRRRWXNR-QOBXEIRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamidoadenosine 在 potassium [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 5'-N-(2-[18F]fluoroethyl)-2',3'-O-isopropylidene-carboxamidoadenosine
  参考文献：
  名称：

  Synthesis of 5?-N-(2-[18F]fluoroethyl)-carboxamidoadenosine: a promising tracer for investigation of adenosine receptor system by PET technique

  摘要：

  5'-N-(2-[F-18]Fluoroethyl)-carboxamidoadenosine ([F-18]FNECA), a promising F-18-labelled adenosine agonist has been prepared by two different synthetic routes. In the first, [F-18]fluoride was reacted with 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamido-adenosine and after removing the protective group [F-18]FNECA was obtained in a low radiochemical yield (1+/-1%, mean+/-sd, n=7, decay corrected). In the second, 2-[F-18]fluoroethylamine was synthesised according to the literature and reacted with 2',3'-O-isopropylideneadenosine-5'-uronic acid in the presence of a coupling agent. The following hydrolysis step provided the [F-18]FNECA with a modest radiochemical yield (24+/-9%, n=17, based on [F-18]fluoride-activity). After purification by preparative reverse phase HPLC 18.9-166.5 MBq (0.51-4.5 mCi) [F-18]FNECA was obtained with a specific activity of 2.35+/-1.14 TBq/mmol (63.5+/-30.9 Ci/mmol, n=3). The total synthesis took 200 min and the decay corrected radiochemical yield based on [F-18]F- activity was 17+/-9% (n=5) with more than 99.9% radiochemical purity. This second route provides sufficient [F-18]FNECA for the subsequent biological evaluation using PET-technique.

  DOI：

  10.1002/1099-1344(200007)43:8<807::aid-jlcr365>3.0.co;2-k
• 作为产物：
  描述：

  2',3'-异丙叉腺苷 在 吡啶 、 氢氧化钾 、 potassium permanganate 、 N,N'-二异丙基碳二亚胺 作用下， 以 水 为溶剂， 反应 72.0h， 生成 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamidoadenosine
  参考文献：
  名称：

  Synthesis of 5?-N-(2-[18F]fluoroethyl)-carboxamidoadenosine: a promising tracer for investigation of adenosine receptor system by PET technique

  摘要：

  5'-N-(2-[F-18]Fluoroethyl)-carboxamidoadenosine ([F-18]FNECA), a promising F-18-labelled adenosine agonist has been prepared by two different synthetic routes. In the first, [F-18]fluoride was reacted with 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamido-adenosine and after removing the protective group [F-18]FNECA was obtained in a low radiochemical yield (1+/-1%, mean+/-sd, n=7, decay corrected). In the second, 2-[F-18]fluoroethylamine was synthesised according to the literature and reacted with 2',3'-O-isopropylideneadenosine-5'-uronic acid in the presence of a coupling agent. The following hydrolysis step provided the [F-18]FNECA with a modest radiochemical yield (24+/-9%, n=17, based on [F-18]fluoride-activity). After purification by preparative reverse phase HPLC 18.9-166.5 MBq (0.51-4.5 mCi) [F-18]FNECA was obtained with a specific activity of 2.35+/-1.14 TBq/mmol (63.5+/-30.9 Ci/mmol, n=3). The total synthesis took 200 min and the decay corrected radiochemical yield based on [F-18]F- activity was 17+/-9% (n=5) with more than 99.9% radiochemical purity. This second route provides sufficient [F-18]FNECA for the subsequent biological evaluation using PET-technique.

  DOI：

  10.1002/1099-1344(200007)43:8<807::aid-jlcr365>3.0.co;2-k

文献信息

• Synthesis of 5?-N-(2-[18F]fluoroethyl)-carboxamidoadenosine: a promising tracer for investigation of adenosine receptor system by PET technique
  作者：Sz. Lehel、G. Horv�th、I. Boros、P. Mikecz、T. M�ri�n、A. J. Szentmikl�si、L. Tr�n

  DOI：10.1002/1099-1344(200007)43:8<807::aid-jlcr365>3.0.co;2-k

  日期：2000.7

  5'-N-(2-[F-18]Fluoroethyl)-carboxamidoadenosine ([F-18]FNECA), a promising F-18-labelled adenosine agonist has been prepared by two different synthetic routes. In the first, [F-18]fluoride was reacted with 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamido-adenosine and after removing the protective group [F-18]FNECA was obtained in a low radiochemical yield (1+/-1%, mean+/-sd, n=7, decay corrected). In the second, 2-[F-18]fluoroethylamine was synthesised according to the literature and reacted with 2',3'-O-isopropylideneadenosine-5'-uronic acid in the presence of a coupling agent. The following hydrolysis step provided the [F-18]FNECA with a modest radiochemical yield (24+/-9%, n=17, based on [F-18]fluoride-activity). After purification by preparative reverse phase HPLC 18.9-166.5 MBq (0.51-4.5 mCi) [F-18]FNECA was obtained with a specific activity of 2.35+/-1.14 TBq/mmol (63.5+/-30.9 Ci/mmol, n=3). The total synthesis took 200 min and the decay corrected radiochemical yield based on [F-18]F- activity was 17+/-9% (n=5) with more than 99.9% radiochemical purity. This second route provides sufficient [F-18]FNECA for the subsequent biological evaluation using PET-technique.