3-[18F]fluoropropyl p-tosylate | 113426-14-5

• 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: 3-[18F]fluoropropyl p-tosylate
• 英文别名: [¹⁸F]-3-(fluoro)propyl 4-methylbenzenesulfonate；3-[¹⁸F]fluoropropyl 4-methylbenzenesulfonate；3-[¹⁸F]fluoropropyl-4-methylbenzenesulfonate；3-[¹⁸F]-fluoropropyl tosylate；3-[¹⁸F]fluoropropyl tosylate；3-[¹⁸]fluoropropyl tosylate；3-(18F)fluoranylpropyl 4-methylbenzenesulfonate
• CAS: 113426-14-5
• 化学式: C₁₀H₁₃FO₃S
• 分子量: 231.277
• InChiKey: PYCKJIAEKJWSKM-KXMUYVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[18F]fluoropropyl p-tosylate 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 0.17h， 生成 O-(3-[18F]fluoropropyl)-D-tyrosine
  参考文献：
  名称：

  RADIOACTIVE TYROSINE DERIVATIVE, METHOD FOR PRODUCING SAME, LABELING AGENT FOR POSITRON IMAGING AND MEDICAL AGENT FOR ASSESSING GRADE OF MALIGNANCY OF TUMOR RESPECTIVELY COMPOSED OF RADIOACTIVE TYROSINE DERIVATIVE, AND METHOD FOR DETECTING TUMOR

  摘要：

  公开号：

  EP1749815B1
• 作为产物：
  描述：

  对甲苯磺酰氯 在 sodium fluoride 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.25h， 生成 3-[18F]fluoropropyl p-tosylate
  参考文献：
  名称：

  Synthesis and Cardiac Imaging of ¹⁸F-Ligands Selective for β₁-Adrenoreceptors

  摘要：

  A series of potent and selective beta(1)-adrenoreceptor ligands were identified (IC50 range, 0.04-0.25 nM; beta(1)/beta(2) selectivity range, 65-450-fold), labeled with the PET radioisotope fluorine-18 and evaluated in normal Sprague-Dawley rats. Tissue distribution studies demonstrated uptake of each radiotracers from the blood pool into the myocardium (0.48-0.62% ID/g), lung (0.63-0.97% ID/g), and liver (1.03-1.14% ID/g). Dynamic mu PET imaging confirmed the in vivo dissection studies.

  DOI：

  10.1021/ml1002458

文献信息

• Fast and reliable generation of [¹⁸F]triflyl fluoride, a gaseous [¹⁸F]fluoride source
  作者：A. Pees、C. Sewing、M. J. W. D. Vosjan、V. Tadino、J. D. M. Herscheid、A. D. Windhorst、D. J. Vugts

  DOI：10.1039/c8cc03206h

  日期：——

  [18F]fluoride has been developed, omitting time consuming azeotropic drying procedures. Gaseous [18F]triflyl fluoride is formed instantaneously at room temperature from hydrated [18F]fluoride, followed by distillation in less than 5 minutes into a dry aprotic solvent, in which dry [18F]fluoride is released in presence of base with >90% radiochemical yield. The reactivity of the [18F]fluoride has been

  已经开发了一种生产反应性[ 18 F]氟化物的新方法，省却了耗时的共沸干燥程序。在室温下由水合的[ 18 F]氟化物瞬时形成气态[ 18 F]三氟氟化物，然后在不到5分钟的时间内蒸馏至干燥的非质子溶剂中，在碱的存在下在其中释放出干燥的[ 18 F]氟化物。 > 90％的放射化学收率。的反应性[ 18 F]氟化物已经证实通过用几个模型化合物反应，并通过在PET示踪剂[合成18 F]氟雌二醇（[ 18 F] FES）和ö -2- [ 18 F] fluoroethyl-L-酪氨酸（[ 18 F] FET），具有良好的分离放射化学产率和高达123 GBqμmol -1的摩尔活性。
• [EN] INHIBITOR IMAGING AGENTS<br/>[FR] AGENTS INHIBITEURS D'IMAGERIE
  申请人：AMERSHAM PLC

  公开号：WO2005049005A1

  公开（公告）日：2005-06-02

  The present invention discloses that imaging agents which comprise a specific type of matrix metalloproteinase inhibitors (MMPi's) of the sulphonamide hydroxamate class labelled with an imaging moiety, are useful diagnostic imaging agents for in vivo imaging and diagnosis of the mammalian body.

  本发明揭示了一种成像试剂，其中包括一种特定类型的矩阵金属蛋白酶抑制剂（MMPi's），属于磺胺基羟肟类，并标记有成像基团，可用于哺乳动物体内成像和诊断的诊断成像试剂。
• ALPHA-SYNUCLEIN LIGANDS
  申请人：Washington University

  公开号：US20170189566A1

  公开（公告）日：2017-07-06

  The present invention generally relates to various compounds that are useful as α-synuclein ligands. The invention further relates to methods of using these compounds and their radiolabeled analogs for the detection of synucleinopathies, including Parkinson's disease (PD).

  本发明通常涉及作为α-突触核蛋白配体有用的各种化合物。该发明进一步涉及使用这些化合物及其放射标记类似物用于检测突触核蛋白病，包括帕金森病（PD）的方法。
• Radiosynthesis of 3-(3-[18F]fluoropropoxy)-4-(benzyloxy)-N-[(1-dimethylaminocyclopentyl)methyl]-5-methoxybenzamide, a potential PET radiotracer for the glycine transporter GlyT-2
  作者：Haibin Tian、Rebecca Vogel、Louis Amici、Gilles Tamagnan、Ronald M. Baldwin

  DOI：10.1002/jlcr.1145

  日期：2006.12

  The recently described selective and potent GlyT2 antagonist, 4-benzyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide (IC50=16 nM) provided an important additional tool to further characterize GlyT2 pharmacology. In order to identify an effective PET radioligand for in vivo assessment of the GlyT-2 transporter, 3-(3-[18F]fluoropropoxy)-4-(benzyloxy)-N-((1-dimethylaminocyclopentyl) methyl)-5-methoxybenzamide ([18F]3), a novel analog of 4-benzyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide was synthesized using a one-pot, two-step method. The NCA radiofluorination of 1,3-propanediol di-p-tosylate in the presence of K2CO3 and Kryptofix-222 in acetonitrile gave 81% 3-[18F]fluoropropyl tosylate, which was subsequently coupled with 4-benzyloxy-3-hydroxy-5-methoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide in the same reaction vessel. Solvent extraction and HPLC (Eclipse XDB-C8 column, 80/20/0.1 MeOH/H2O/Et3N, 3.0 ml/min) gave [18F]3 in 98.5% radiochemical purity. The radiochemical yield was determined to be 14.0–16.2% at EOS, and the specific activity was 1462±342 GBq/µmol. The time of synthesis and purification was 128 min. The final product was prepared as a sterile saline solution suitable for in vivo use. Copyright © 2006 John Wiley & Sons, Ltd.

  最近描述的选择性和高效的GlyT2拮抗剂4-苄氧基-3,5-二甲氧基-N-[(1-二甲氨基环戊基)甲基]苯酰胺（IC50=16 nM）为进一步表征GlyT2药理学提供了一个重要的额外工具。为了寻找一种有效的PET放射配体用于GlyT-2转运体的体内评估，合成了3-(3-[18F]氟丙氧基)-4-(苄氧基)-N-((1-二甲氨基环戊基)甲基)-5-甲氧基苯酰胺（[18F]3），这是4-苄氧基-3,5-二甲氧基-N-[(1-二甲氨基环戊基)甲基]苯酰胺的新型类似物，采用一步法两步合成。将1,3-丙二醇二-p-托烯-磺酸酯与K2CO3和Kryptofix-222在乙腈中进行NCA放射氟化，获得81%的3-[18F]氟丙基托烯-磺酸酯，随后与4-苄氧基-3-羟基-5-甲氧基-N-[(1-二甲氨基环戊基)甲基]苯酰胺在同一反应容器中偶联。溶剂提取和高效液相色谱（Eclipse XDB-C8柱，80/20/0.1 MeOH/H2O/Et3N，流速为3.0 ml/min）获得了98.5%的[18F]3放射化学纯度。放射化学产率在EOS时被测定为14.0–16.2%，特定活度为1462±342 GBq/μmol。合成和纯化所需时间为128分钟。最终产品以适合体内使用的无菌生理盐水溶液形式制备。版权 © 2006 John Wiley & Sons, Ltd.
• Synthesis ofN-(3-[18F]Fluoropropyl)-2β-carbomethoxy-3β-(4-iodophenyl)nortropane ([18F]FP-β-CIT)
  作者：R. P. Klok、P. J. Klein、J. D. M. Herscheid、A. D. Windhorst

  DOI：10.1002/jlcr.1043

  日期：2006.2

  N-(3-[18F]fluoropropyl)-2β-carbomethoxy-3β-(4-iodophenyl)nortropane ([18F]FP-β-CIT) was synthesized in a two-step reaction sequence. In the first reaction, 1-bromo-3-(nitrobenzene-4-sulfonyloxy)-propane was fluorinated with no-carrier-added fluorine-18. The resulting product, 1-bromo-3-[18F]-fluoropropane, was distilled into a cooled reaction vessel containing 2β-carbomethoxy-3β-(4-iodophenyl)-nortropane

  N-(3-[18F] 氟丙基)-2β-carbomethoxy-3β-(4-iodophenyl)nortropane ([18F]FP-β-CIT) 在两步反应序列中合成。在第一个反应中，1-溴-3-（硝基苯-4-磺酰氧基）-丙烷与未添加载体的氟 18 氟化。将所得产物 1-溴-3-[18F]-氟丙烷蒸馏到含有 2β-碳甲氧基-3β-(4-碘苯基)-去甲托烷、二异丙基乙胺和碘化钾的冷却反应容器中。30分钟后，对反应混合物进行制备型HPLC纯化。产物 [18F]FP-β-CIT 通过固相萃取从 HPLC 洗脱液中分离出来，并配制成等渗、无热原和无菌的 [18F]FP-β-CIT 溶液。整体衰减校正的放射化学产率为 25 ± 5%。放射化学纯度为 > 98%，合成结束时的比活为 94 ± 50 GBq/µmol。版权所有 © 2006 John Wiley & Sons, Ltd.