1-(111C)methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene | 1062484-68-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-(111C)methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene
• CAS: 1062484-68-7
• 化学式: C₁₉H₂₀O₃S
• 分子量: 327.421
• InChiKey: RAUHMMADXJJVRP-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [11C]methyl iodide 、 4-[2-(4-(methanesulfonyl)phenyl]cyclopent-1-enyl)phenol 在 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.05h， 生成 1-(111C)methoxy-4-[2-(4-methylsulfonylphenyl)cyclopenten-1-yl]benzene
  参考文献：
  名称：

  Synthesis and evaluation in vitro and in vivo of a 11C-labeled cyclooxygenase-2 (COX-2) inhibitor

  摘要：

  The radiosynthesis and radiopharmacological evaluation of 1-[C-11] methoxy-4-(2-(4-(methanesulfonyl)phenyl)cyclopent-1-enyl)-benzene [C-11]5 as novel PET radiotracer for imaging of COX-2 expression is described\. The radiotracer was prepared via O-methylation reaction with [C-11] methyl iodide in 19% decay-corrected radiochemical yield at a specific activity of 20-25 GBq/mu mol at the end-of-synthesis within 35 min. The radiotracer [C-11]5 was evaluated in vitro using various pro-inflammatory and tumor cell lines showing high functional expression of COX-2 at baseline or after induction. In vivo biodistribution of compound [C-11] 5 was characterized in male Wistar rats. Compound [C-11]5 was rapidly metabolized in rat plasma, and more pronounced, in mouse plasma. In vivo kinetics and tumor uptake were demonstrated by dynamic small animal PET studies in a mouse tumor xenograft model. Tumor uptake of radioactivity was clearly visible overtime. However, radioactivity uptake in the tumor could not be blocked by the pre-injection of nonradioactive compound 5. Therefore, it can be concluded that radioactivity uptake in the tumor was not COX-2 mediated. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.016

文献信息

• Synthesis and evaluation in vitro and in vivo of a 11C-labeled cyclooxygenase-2 (COX-2) inhibitor
  作者：Frank Wuest、Torsten Kniess、Ralf Bergmann、Jens Pietzsch

  DOI：10.1016/j.bmc.2008.07.016

  日期：2008.8

  The radiosynthesis and radiopharmacological evaluation of 1-[C-11] methoxy-4-(2-(4-(methanesulfonyl)phenyl)cyclopent-1-enyl)-benzene [C-11]5 as novel PET radiotracer for imaging of COX-2 expression is described\. The radiotracer was prepared via O-methylation reaction with [C-11] methyl iodide in 19% decay-corrected radiochemical yield at a specific activity of 20-25 GBq/mu mol at the end-of-synthesis within 35 min. The radiotracer [C-11]5 was evaluated in vitro using various pro-inflammatory and tumor cell lines showing high functional expression of COX-2 at baseline or after induction. In vivo biodistribution of compound [C-11] 5 was characterized in male Wistar rats. Compound [C-11]5 was rapidly metabolized in rat plasma, and more pronounced, in mouse plasma. In vivo kinetics and tumor uptake were demonstrated by dynamic small animal PET studies in a mouse tumor xenograft model. Tumor uptake of radioactivity was clearly visible overtime. However, radioactivity uptake in the tumor could not be blocked by the pre-injection of nonradioactive compound 5. Therefore, it can be concluded that radioactivity uptake in the tumor was not COX-2 mediated. (C) 2008 Elsevier Ltd. All rights reserved.