[¹¹C]bexarotene | 1572536-64-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [¹¹C]bexarotene
• 英文别名: 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
• CAS: 1572536-64-1
• 化学式: C₂₄H₂₈O₂
• 分子量: 347.474
• InChiKey: NAVMQTYZDKMPEU-KVTPGWOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  6-(1-(4-iodophenyl)vinyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene 在 [11C]二氧化碳 、 N-XantPhos 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 [¹¹C]bexarotene
  参考文献：
  名称：

  Automated production of ¹¹C‐labeled carboxylic acids and esters via “in‐loop” ¹¹C‐carbonylation using GE FX synthesis modules

  摘要：

  我们开发出了一种从卤化物前体辐射合成 11C 羧酸和酯的内环 11C 羧化工艺。该反应在室温、温和的条件下进行，可对缺电子和富电子（杂）芳香卤化物进行 11C 羰基化反应，提供 11C 羧酸和酯，具有良好到极佳的放射化学收率、高放射化学纯度和出色的摩尔活性。该过程利用商业放射化学合成模块实现了完全自动化，并通过[11C]贝沙罗汀和[11C]乙酰乙酸的 cGMP 放射合成验证了其在临床生产中的应用。

  DOI：

  10.1002/jlcr.4058

文献信息

• Synthesis of [¹¹C]Bexarotene by Cu-Mediated [¹¹C]Carbon Dioxide Fixation and Preliminary PET Imaging
  作者：Benjamin H. Rotstein、Jacob M. Hooker、Jiyeon Woo、Thomas Lee Collier、Thomas J. Brady、Steven H. Liang、Neil Vasdev

  DOI：10.1021/ml500065q

  日期：2014.6.12

  Bexarotene (Targretin) is a retinoid X receptor (RXR) agonist that has applications for treatment of T cell lymphoma and proposed mechanisms of action in Alzheimer's disease that have been the subject of recent controversy. Carbon-11 labeled bexarotene ([11C_ carbony1]4-[1-(3,5,5,8,8-pentamethylietralin-2-yOethenyllbenzoic acid) was synthesized using a Cu-mediated cross-coupling reaction employing an arylboronate precursor 1 and [C-11]carbon dioxide under atmospheric pressure in 15 +/- 2% uncorrected radiochemical yield (n = 3), based on [C-11]CO2. Judicious choice of solvents, catalysts, and additives, as well as precursor concentration and purity of [11C]CO2, enabled the preparation of this C-11-labeled carboxylic acid. Formulated [11C]bexarotene was isolated (>37 mCi) with >99% radiochemical purity in 32 mm. Preliminary positron emission tomography magnetic resonance imaging revealed rapid brain uptake in nonhuman primate in the first 75 s following intravenous administration of the radiotracer (specific activity >0.3 Ci/mu mol at time of injection), followed by slow clearance (Delta = 43%) over 60 min. Modest uptake (SUV = 0.8) was observed in whole brain and regions with high RXR expression.