(+)-(1S,5R,6R)-5-(8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]oct-6-yl)-N,N,N-trimethylpyridine-2-aminium iodide | 1581780-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (+)-(1S,5R,6R)-5-(8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]oct-6-yl)-N,N,N-trimethylpyridine-2-aminium iodide
• CAS: 1581780-63-3
• 化学式: C₂₀H₃₂N₃O₂*I
• 分子量: 473.397
• InChiKey: TZIIPQSWQJBXGO-NINZUIERSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.43
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-(1S,5R,6R)-5-(8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]oct-6-yl)-N,N,N-trimethylpyridine-2-aminium iodide 在 盐酸 、 potassium carbonate 、 溶剂黄146 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 生成 (+)-(1S,5R,6R)-6-(6-[18F]fluoro-pyridine-3-yl)-8-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis and biological evaluation of both enantiomers of [18F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors

  摘要：

  Both enantiomers of the epibatidine analogue flubatine display high affinity towards the alpha 4 beta 2 nicotinic acetylcholine receptor (nAChR) in vitro, accompanied by negligible interactions with diverse off-target proteins. Extended single dose toxicity studies in rodent indicated a NOEL (No Observed Effect Level) of 6.2 mu g/kg for (-)-flubatine and 1.55 mu g/kg for (+)-flubatine. We developed syntheses for both flubatine enantiomers and their corresponding precursors for radiolabeling. The newly synthesized trimethylammonium precursors allowed for highly efficient F-18-radiolabelling in radiochemical yields >60% and specific activities >750 GBq/mu mol, thus making the radioligands practical for clinical investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.011
• 作为产物：
  描述：

  exo-6-(6-fluoro-pyridin-3-yl)-3-(imidazole-1-carbothioyloxy)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester 在 偶氮二异丁腈 、 palladium 10% on activated carbon 、 三正丁基氢锡 、 potassium carbonate 、 三乙胺 、 环己烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二乙胺 、 甲苯 、 乙腈 为溶剂， 反应 168.5h， 生成 (+)-(1S,5R,6R)-5-(8-tert-butoxycarbonyl-8-azabicyclo[3.2.1]oct-6-yl)-N,N,N-trimethylpyridine-2-aminium iodide
  参考文献：
  名称：

  Synthesis and biological evaluation of both enantiomers of [18F]flubatine, promising radiotracers with fast kinetics for the imaging of α4β2-nicotinic acetylcholine receptors

  摘要：

  Both enantiomers of the epibatidine analogue flubatine display high affinity towards the alpha 4 beta 2 nicotinic acetylcholine receptor (nAChR) in vitro, accompanied by negligible interactions with diverse off-target proteins. Extended single dose toxicity studies in rodent indicated a NOEL (No Observed Effect Level) of 6.2 mu g/kg for (-)-flubatine and 1.55 mu g/kg for (+)-flubatine. We developed syntheses for both flubatine enantiomers and their corresponding precursors for radiolabeling. The newly synthesized trimethylammonium precursors allowed for highly efficient F-18-radiolabelling in radiochemical yields >60% and specific activities >750 GBq/mu mol, thus making the radioligands practical for clinical investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.011