methyl 2-phenyl-[3-(11)C]propionate | 1257315-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-phenyl-[3-(11)C]propionate
• 英文别名: (11)C-methyl 2-phenylpropanoate
• CAS: 1257315-84-6
• 化学式: C₁₀H₁₂O₂
• 分子量: 163.193
• InChiKey: DZIQUZJSNSZOCH-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.96
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  [11C]methyl iodide 、 苯乙酸甲酯 在 四丁基氟化铵 作用下， 以 二甲基亚砜 为溶剂， 反应 0.01h， 生成 methyl 2-phenyl-[3-(11)C]propionate
  参考文献：
  名称：

  Efficient synthesis and chiral separation of 11C-labeled ibuprofen assisted by DMSO for imaging of in vivo behavior of the individual isomers by positron emission tomography

  摘要：

  The pharmacological mechanisms focusing on chiral isomer of ibuprofen are not fully understood. Only the (S)-isomer of ibuprofen inhibits cyclooxygenases, which mediates the generation of prostanoids and thromboxanes. Consequently, (S)-isomers represent a major promoter of the anti-inflammatory effect, and the effects of the (R)-isomers have not been widely discussed. However, more recently, the cyclooxygenase-independent pharmacological effects of ibuprofen have been elucidated. Pharmacokinetic studies with individual isomers of ibuprofen by positron emission tomography should aid our understanding of the pharmacological mechanisms of ibuprofen. The efficient C-11-labeling of ibuprofen for chiral separation via the TBAF-promoted alpha-[C-11]methylation was achieved by using DMSO rather than THF as the reaction solvent. The robust production of the radiochemically labile C-11-labeled ibuprofen ester was realized by the protective effect of DMSO on radiolysis. After intravenous injection of each enantiomer of [C-11]ibuprofen, significantly high radioactivity was observed in the joints of arthritis mice when compared to the levels observed in normal mice. However, the high accumulation was equivalent between the enantiomers, indicating that ibuprofen is accumulated in the arthritic joints regardless of the expression of cyclooxygenases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.03.041

文献信息

• Tetrabutylammonium fluoride-promoted α-[11C]methylation of α-arylesters: a simple and robust method for the preparation of 11C-labeled ibuprofen
  作者：Koichi Kato、Tatsuya Kikuchi、Nobuki Nengaki、Takuya Arai、Ming-Rong Zhang

  DOI：10.1016/j.tetlet.2010.09.007

  日期：2010.11

  Tetrabutylammonium fluoride-promoted alpha-[C-11]methylation of alpha-arlylesters was developed. The method was amenable to the remote-controlled synthesis of C-11-labeled ibuprofen. (C) 2010 Elsevier Ltd. All rights reserved.