[11C]methyl triflate | 145577-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [11C]methyl triflate
• 英文别名: [¹¹C]methyl trifluoromethanesulfonate；<11C>methyl triflate；[¹¹C]CH₃OTf；¹¹C-MeOTf；(111C)methyl trifluoromethanesulfonate
• CAS: 145577-00-0
• 化学式: C₂H₃F₃O₃S
• 分子量: 163.094
• InChiKey: OIRDBPQYVWXNSJ-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [11C]methyl triflate 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.16h， 以35%的产率得到[O-methyl-11C]2-{4-[4-(7-Methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione
  参考文献：
  名称：

  WO2006/83424

  摘要：

  公开号：
• 作为产物：
  描述：

  [11C]二氧化碳 在 silver trifluoromethanesulfinate 作用下， 生成 [11C]methyl triflate
  参考文献：
  名称：

  Radiosynthesis of New Carbon-11-labeled Nimesulide Analogs as Potential PET SAER Tracers for Imaging of Aromatase Expression in Breast Cancer

  摘要：

  Carbon-11-labeled nimesulide analogs, N-[11C]methyl-N-(2-benzyloxy-4-nitrophenyl)methanesulfonamide ([11C]4a), N-[11C]methyl-N-[2-(4'-methylbenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]4b), N-[11C]methyl-N-[2-(4'-fluorobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]4c), N-[11C]methyl-N-[2-(4'-nitrobenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]8a), N-[11C]methyl-N-[2-(-naphthylmethoxy)-4-nitrophenyl]methanesulfonamide ([11C]8b), and N-[11C]methyl-N-[2-(2'-phenylbenzyloxy)-4-nitrophenyl]methanesulfonamide ([11C]8c), have been synthesized as new potential positron emission tomography (PET) selective aromatase expression regulator (SAER) radiotracers for imaging of aromatase expression in breast cancer. The target tracers were prepared by N-[11C]methylation of their corresponding precursors using [11C]CH3OTf under basic conditions (NaH) and isolated by reversed-phase high-pressure liquid chromatography (HPLC) method in 30-50% radiochemical yields decay corrected to end of bombardment (EOB) with 25-30min overall synthesis time and 111-148 GBq/mol specific activity at end of synthesis (EOS).

  DOI：

  10.1080/00397910903013747

文献信息

• 亚氨基酸类PET显像剂及其制备方法与应用
  申请人：广东回旋医药科技股份有限公司

  公开号：CN103333079B

  公开（公告）日：2016-08-17

  本发明公开了一种亚氨基酸类正电子发射断层(PET)显像剂及其制备方法和应用，其属于N‑取代正电子核素标记谷氨基酸类化合物，其结构为：其中，L*＝‑11CH3，‑CH2CH218F，‑COCH(18F)CH3；新型显像剂N‑(2‑18F‑氟丙酰基)‑谷氨酸显示很好的肿瘤PET显像灵敏性和特异性，对肿瘤(如S180纤维肉瘤)有很高的摄取，并且体内其他组织器官(除膀胱外)摄取不明显，显示了高的肿瘤与本底比值。体内外实验表明N‑(2‑18F‑氟丙酰基)‑谷氨酸在体内外较稳定，显示了很好的药代动力学特性。
• Synthesis, In Vivo Occupancy, and Radiolabeling of Potent Phosphodiesterase Subtype-10 Inhibitors as Candidates for Positron Emission Tomography Imaging
  作者：José-Ignacio Andrés、Meri De Angelis、Jesús Alcázar、Laura Iturrino、Xavier Langlois、Stefanie Dedeurwaerdere、Ilse Lenaerts、Greet Vanhoof、Sofie Celen、Guy Bormans

  DOI：10.1021/jm200536d

  日期：2011.8.25

  for in vivo imaging using positron emission tomography (PET). We now describe the synthesis and biological evaluation of a series of related pyridinyl analogues that exhibit high potency and selectivity as PDE10A inhibitors. The most interesting compounds were injected in rats to measure their levels of PDE10A occupancy through an in vivo occupancy assay. The 3,5-dimethylpyridine derivative 3 and the

  我们最近报道了磷酸二酯酶10A（PDE10A）抑制剂2- [4- [1-（2- [ 18 [ ] F]氟乙基）-4-吡啶-4-4-基-1 H-吡唑-3-基]-苯氧基甲基]-喹啉（[ 18 F] 1a）是使用正电子发射断层扫描（PET）进行体内成像的有前途的候选物。现在，我们描述了一系列相关的吡啶基类似物的合成和生物学评估，这些吡啶基类似物作为PDE10A抑制剂具有很高的效力和选择性。将最有趣的化合物注射到大鼠中，以通过体内占有率测定法测量其PDE10A占有率水平。3,5-二甲基吡啶衍生物3和5-甲氧基吡啶衍生物4的可比性与1a。因为这些衍生物显示出较低的体外活性，并且比1a的亲脂性略低，所以我们假设它们可以表现为更好的PET成像配体。放射性合成化合物[ 18 F] 3，[ 18 F] 4和[ 11 C] 4并在大鼠中进行生物分布研究，作为在脑中对PDE10A进行体内成像的候选PET放射性配体进行初步评估。
• Deuterium Kinetic Isotope Effect Studies of a Potential <i>in Vivo</i> Metabolic Trapping Agent for Monoamine Oxidase B
  作者：Lindsey R. Drake、Allen F. Brooks、Anthony J. Mufarreh、Jonathan M. Pham、Robert A. Koeppe、Xia Shao、Peter J. H. Scott、Michael R. Kilbourn

  DOI：10.1021/acschemneuro.8b00219

  日期：2018.12.19

  improve on the in vivo pharmacokinetics of [11C]Cou by using the deuterium kinetic isotope effect (KIE) to slow the MAO-B-mediated oxidation step and thus reduce the rate of trapping in brain tissues. However, in vitro assays of enzyme kinetics and in vivo PET imaging of pharmacokinetics in primate brain showed no effects of deuterium substitution on the tetrahydropyridine ring of [11C]Cou. The results

  可视化单胺氧化酶B（MAO-B）的体内活性是正在进行的神经退行性星形胶质变性研究的重要工具。成像MAO酶表达或活性变化的现有策略已利用不可逆的自杀抑制剂或高亲和力可逆结合抑制剂作为正电子发射断层扫描（PET）配体。作为一种替代方法，我们开发了4-甲基-7-[（1- [11C]甲基-1,2,3,6-四氢吡啶-4-基）氧基] -2 H-铬-2-（1 ] Cou）作为MAO-B的代谢捕获剂。在恒河猴脑中捕获[11C] Cou证明了MAO-B的选择性。在这项工作中，我们试图通过使用氘动力学同位素效应（KIE）来减慢MAO-B介导的氧化步骤，从而降低[11C] Cou的体内药代动力学，从而降低在脑组织中的捕获率。但是，在灵长类动物大脑中进行的酶动力学体外分析和体内药代动力学的PET成像显示，氘取代对[11C] Cou的四氢吡啶环没有影响。结果可能是由于新成像剂整体代谢中的第二步掩盖了KIE。
• Highly efficient synthesis of [11C]Me-QNB, a selective radioligand for the quantification of the cardiac muscarinic receptors using PET
  作者：Fr�d�ric Dolle、Fran�oise Hinnen、Fran�oise Vaufrey、St�phane Demphel、Yann Bramoulle、Denis Fournier、Michel Ponchant、H�ric Valette、Christian Crouzel

  DOI：10.1002/jlcr.460

  日期：2001.4

  Me-QNB (N-methyl-quinuclidin-3-yl benzilate or N-methyl-quinuclidin-3-yl diphenylhydroxy acetate) is a hydrophilic, non-metabolized and highly specific muscarinic acetylcholinergic antagonist. Using this quaternary ammonium derivative of QNB, labelled with carbon-11, a positron-emitting isotope (half-life : 20.4 minutes), the potential for quantification of myocardial muscarinic receptors in vivo using the high-resolution, sensitive and quantitative imaging technique PET (positron emission tomography) was previously demonstrated in dogs and validated in humans. In this paper, the radiosynthesis of carbon-11-labelled Me-QNB is investigated and oriented towards the preparation of multi milliCuries of radiotracer. Typically, using no-carrier-added [11C]methyl triflate as the alkylating agent and 0.64 mg (1.89 µmol) of QNB as precursor for labelling at 100°C for 1 minute lead to a 48.5% +/−10% (15 runs) decay-corrected radiochemical yield (based on [11C]methyl triflate). 183 mCi (+/−39) of [11C]Me-QNB ([11C]-1) could be synthesized in only 27 to 28 minutes after EOB and occasionally, up to 340 mCi of [11C]Me-QNB ([11C]-1) were obtained, corresponding to a 85% decay-corrected yield. The associated decay-corrected specific radioactivities obtained were 2658 mCi/µmol (+/−971) at EOB. Copyright © 2001 John Wiley & Sons, Ltd.

  Me-QNB (N-甲基-喹宁环-3-基苄酯或N-甲基-喹宁环-3-基二苯羟乙酸酯)是一种亲水性、非代谢性和高度特异性的毒蕈碱型乙酰胆碱拮抗剂。使用这种标记有碳-11(一种正电子发射同位素，半衰期为20.4分钟)的QNB四级铵衍生物，先前已在狗中证明了利用高分辨率、灵敏和定量的成像技术(正电子发射断层扫描，PET)对心肌毒蕈碱受体进行定量测量的潜力，并在人类中得到了验证。本文研究了碳-11标记的Me-QNB的放射合成，旨在制备多毫居里的放射性示踪剂。通常，使用无载体添加的[11C]甲基三氟甲磺酸酯作为烷基化剂，并以0.64 mg (1.89 µmol)的QNB作为标记前体，在100°C下标记1分钟，得到48.5% ±10%(15次运行)的衰变校正放射化学产率(基于[11C]甲基三氟甲磺酸酯)。在EOB后仅27到28分钟内可以合成183 mCi (±39)的[11C]Me-QNB ([11C]-1)，偶尔可获得高达340 mCi的[11C]Me-QNB ([11C]-1)，对应于85%的衰变校正产率。在EOB时获得的关联衰变校正比活度为2658 mCi/µmol (±971)。版权所有 © 2001 John Wiley & Sons, Ltd.
• Towards tropomyosin-related kinase B (TrkB) receptor ligands for brain imaging with PET: Radiosynthesis and evaluation of 2-(4-[18F]fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one and 2-(4-([N-methyl-11C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one
  作者：Vadim Bernard-Gauthier、Mehdi Boudjemeline、Pedro Rosa-Neto、Alexander Thiel、Ralf Schirrmacher

  DOI：10.1016/j.bmc.2013.10.012

  日期：2013.12

  linked to numerous neurodegenerative diseases and conditions. Herein we report the synthesis, biological evaluation and radiosynthesis of the first TrkB radioligands based on the recently identified 7,8-dihydroxyflavone chemotype. 2-(4-[18F]fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one ([18F]10b) was synthesized in high radiochemical yields via an efficient SNAr radiofluorination involving a para-Michael

  原肌球蛋白相关激酶B（TrkB）与同源配体脑源性神经营养因子（BDNF）的相互作用介导了神经系统发育的基本途径。TrkB信号改变与许多神经退行性疾病和状况有关。在这里，我们报告基于最近确定的7,8-二羟基黄酮化学型的第一个TrkB放射性配体的合成，生物学评估和放射性合成。通过高效的S N Ar放射性氟化，涉及对位-，以高放射化学收率合成了2-（4- [ 18 F]氟苯基）-7,8-二羟基-4 H -chromen-4-one（[ 18 F] 10b）。迈克尔受体取代的芳基，接着是BBr 3-促进的双去甲基化。选择性的N- [ 11 C]甲基化得到2-（4-（[ N-甲基-11 C]-二甲基氨基）苯基）-7,8-二羟基-4 H-铬烯-4-酮（[ 11 C] 10c）从具有[ 11 C] MeOTf的完全脱保护的含邻苯二酚的去甲甲基前体13中分离得到。[ 18 F] 10b的体外放射自显影具有