tert-butyl N-(tert-butoxycarbonyl)-S-(3-chloropropyl)-homocysteinate | 1245941-94-9

• 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: tert-butyl N-(tert-butoxycarbonyl)-S-(3-chloropropyl)-homocysteinate
• 英文别名: tert-butyl (2S)-4-(3-chloropropylsulfanyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1245941-94-9
• 化学式: C₁₆H₃₀ClNO₄S
• 分子量: 367.938
• InChiKey: CMIQRLVKAJLADK-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl N-(tert-butoxycarbonyl)-S-(3-chloropropyl)-homocysteinate 在 potassium [¹⁸F]fluoride 、 potassium oxalate 、 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 tert-butyl L-(18)F-N-(tert-butoxycarbonyl)-S-(3-fluoropropyl)-homocysteinate
  参考文献：
  名称：

  Radiosynthesis and Biological Evaluation of l- and d-S-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography

  摘要：

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.

  DOI：

  10.1021/jm101513q
• 作为产物：
  描述：

  N,N'-di(tert-butoxycarbonyl)-L-homocystine 在 三丁基膦 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 tert-butyl N-(tert-butoxycarbonyl)-S-(3-chloropropyl)-homocysteinate
  参考文献：
  名称：

  Radiosynthesis and Biological Evaluation of l- and d-S-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography

  摘要：

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.

  DOI：

  10.1021/jm101513q

文献信息

• Radiosynthesis and Biological Evaluation of <scp>l</scp>- and <scp>d</scp>-<i>S</i>-(3-[¹⁸F]Fluoropropyl)homocysteine for Tumor Imaging Using Positron Emission Tomography
  作者：Thomas Bourdier、Rachael Shepherd、Paula Berghofer、Timothy Jackson、Christopher J. R. Fookes、Delphine Denoyer、Donna S. Dorow、Ivan Greguric、Marie-Claude Gregoire、Rodney J. Hicks、Andrew Katsifis

  DOI：10.1021/jm101513q

  日期：2011.3.24

  Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [C-11]methionine has prompted the development of a new F-18-labeled methionine derivative S-(3-[F-18]fluoropropyl)homocysteine ([F-18]FPHCys). The L and D enantiomers of [F-18]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [F-18]fluoride substitution using K-2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [F-18]-L-FPHCys and [F-18]-D-FPHCys were isolated in 20 +/- 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 mm. Competitive Take studies in A375 and HT29 tumor cells suggest that L- and n-[F-18]FPHCys are taken up by the L-transporter system. [F-18]-L-FPHCys and [F-18]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [F-18]-L-FPHCys and [F-18]-D-FPHCys, respectively, at 2 h postinjection.