(11)C-(R)-ibuprofen | 1311284-71-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (11)C-(R)-ibuprofen
• 英文别名: (R)-[11C]-Ibuprofen；(2R)-2-[4-(2-methylpropyl)phenyl](311C)propanoic acid
• CAS: 1311284-71-5
• 化学式: C₁₃H₁₈O₂
• 分子量: 205.274
• InChiKey: HEFNNWSXXWATRW-ZPYIKOFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [11C]-ibuprofen methyl ester 在 sodium hydroxide 作用下， 以 水 、 乙腈 为溶剂， 反应 0.03h， 生成 (11)C-(S)-ibuprofen 、 (11)C-(R)-ibuprofen
  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

• 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
  作者：Tatsuya Kikuchi、Maki Okada、Nobuki Nengaki、Kenji Furutsuka、Hidekatsu Wakizaka、Toshimitsu Okamura、Ming-Rong Zhang、Koichi Kato

  DOI：10.1016/j.bmc.2011.03.041

  日期：2011.5

  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.