[18F]2-fluoroethyl 4-bromobenzenesulfonate | 869845-34-1

• 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: [18F]2-fluoroethyl 4-bromobenzenesulfonate
• 英文别名: 2-[18F]fluoroethyl brosylate；2-(18F)fluoranylethyl 4-bromobenzenesulfonate
• CAS: 869845-34-1
• 化学式: C₈H₈BrFO₃S
• 分子量: 282.12
• InChiKey: FPTGRXPRJSRUMH-LMANFOLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  [18F]2-fluoroethyl 4-bromobenzenesulfonate 、 4-(6-iodo-H-imidazo[1,2-a]pyridin-2-yl)-N-methylbenzenamine 以 乙腈 为溶剂， 反应 0.17h， 生成 6-iodo-2-[4'-N-(2-[18F]fluoroethyl)methylamino]phenylimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Radiosyntheses and reactivities of novel [18F]2-fluoroethyl arylsulfonates

  摘要：

  [18F]2-氟乙基对甲苯磺酸酯([18F]FEOX, X=Ts)广泛用于正电子发射断层扫描(PET)示踪剂的标记。尽管可能具有增强的反应性,但关于合成其他[18F]2-氟乙基芳磺酸酯([18F]FEOX)的研究报道很少,特别是含有较少电富集芳基的化合物。因此,合成了一系列新型[18F]FEOX(X=苯磺酰基、对溴苯磺酰基、对硝基苯磺酰基、3,4-二溴苯磺酰基)并比较了其与[18F]FEOTs的反应活性。放射性标记前体(双乙二醇芳磺酸酯)和参考FEOX通过以下方法合成:乙醇+芳磺酰氯+KOSiMe3(在四氢呋喃中)。无论取代模式如何,[18F]FEOX(110°C, 5 min, 乙腈)均以相似的衰减校正的放射化学产率(RCY; 47–53%)获得。所有[18F]FEOX均提供了优异的多巴胺摄取放射配体[18F]FECNT的RCY(64–87%)(130°C, 10 min, 乙腈)。3,4-二溴苯磺酸酯提供了最高的[18F]FECNT的RCY(87%),该高效液相色谱纯化的标记试剂直接用于高效生产[18F]FECNT。当与淀粉样蛋白探针(HM-IMPY)的二级苯胺或对硝基苯酚反应时,[18F]FEOX的RCY明显高于对溴苯磺酸酯和对硝基苯磺酸酯,而3,4-二溴苯磺酸酯再次提供了最高的RCY。由于新型[18F]FEOX的高反应性和通过稳定前体合成的简便性,这些试剂(特别是3,4-二溴苯磺酸酯)应被视为[18F]FEOTs的替代品。版权所有 © 2005 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.991
• 作为产物：
  描述：

  1,2-bis-(4-bromo-benzenesulfonyl)-ethane 在 fluorine-18 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 乙腈 为溶剂， 生成 [18F]2-fluoroethyl 4-bromobenzenesulfonate
  参考文献：
  名称：

  氟 18 标记的 2beta-carbo(fluoroalkoxy)-3beta-(3'-((Z)-2-haloethenyl)phenyl)nortropanes 的合成、放射合成和生物学评价：用于血清素转运蛋白体内成像的候选放射性配体正电子发射断层扫描。

  摘要：

  间卤乙烯氟烷基酯去甲托烷 1-4 合成为血清素转运蛋白 (SERT) 的配体，用作正电子发射断层扫描 (PET) 成像剂。体外竞争结合测定表明 1-4 对 SERT 具有高亲和力（K(i) 值 = 0.3-0.4 nM），并且对多巴胺和去甲肾上腺素转运蛋白（DAT 和 NET）上的 SERT 具有选择性。[(18)F]1-[(18)F]4 麻醉食蟹猴的 MicroPET 成像表明，所有四种示踪剂的行为相似，在 45-55 分钟后达到富含 SERT 的大脑区域的峰值吸收，然后是稳定的冲刷。对 [(18)F]1 进行的清醒猴子研究表明，[(18)F]1 的摄取不受麻醉影响。用 SERT 配体 15 取代 [(18)F]1-[(18)F]4 的 Chase 研究，

  DOI：

  10.1021/jm800781a

文献信息

• Synthesis, in vitro characterization, and radiolabeling of reboxetine analogs as potential PET radioligands for imaging the norepinephrine transporter
  作者：Fanxing Zeng、Nachwa Jarkas、Jeffrey S. Stehouwer、Ronald J. Voll、Michael J. Owens、Clinton D. Kilts、Charles B. Nemeroff、Mark M. Goodman

  DOI：10.1016/j.bmc.2007.10.025

  日期：2008.1

  Six new (S,S)-enantiomers of reboxetine derivatives were synthesized and their binding affinities were determined via competition binding assays in cells expressing the human norepinephrine transporter (NET), serotonin transporter (SERT) or dopamine transporter (DAT). All six compounds prepared exhibit high affinity for the NET (K(i)

  合成了六种新的瑞波西汀衍生物的 (S,S)-对映异构体，并通过在表达人类去甲肾上腺素转运蛋白 (NET)、血清素转运蛋白 (SERT) 或多巴胺转运蛋白 (DAT) 的细胞中的竞争结合测定来确定它们的结合亲和力。制备的所有六种化合物都对 NET (K(i)
• Synthesis and in Vivo Evaluation of Fluorine-18 and Iodine-123 Labeled 2β-Carbo(2-fluoroethoxy)-3β-(4‘-((<i>Z</i>)-2-iodoethenyl)phenyl)nortropane as a Candidate Serotonin Transporter Imaging Agent
  作者：Christophe Plisson、Jeffrey S. Stehouwer、Ronald J. Voll、Leonard Howell、John R. Votaw、Michael J. Owens、Mark M. Goodman

  DOI：10.1021/jm061303s

  日期：2007.9.1

  and blocking studies performed in male rats demonstrated that [123I]1 was selective and specific for SERT. In vivo microPET brain imaging studies in an anesthetized monkey with [18F]1 showed high uptake in the diencephalon and brainstem with peak uptake achieved at 120 min. A chase study with (R,S)-citalopram.HBr displaced [18F]1 radioactivity from all SERT-rich brain regions. A chase study with the DAT

  合成了2Beta-carbo（2-氟乙氧基）-3beta-（4'-（（（Z）-2-iodoethenyl））苯基降冰片烷（betaFEpZIENT，1）作为5-羟色胺转运蛋白（SERT）成像剂，用于两种正电子发射断层扫描（PET ）和单光子发射计算机断层扫描（SPECT）。1与人单胺转运蛋白的结合亲和力相对于多巴胺转运蛋白（DAT）（Ki = 13 nM）和去甲肾上腺素转运蛋白（NET）（Ki = 28 nM）对SERT（Ki = 0.08 nM）具有高亲和力。在雄性大鼠中进行的体内生物分布和阻断研究表明，[123I] 1对SERT具有选择性和特异性。在[18F] 1麻醉猴子中进行的体内microPET脑成像研究显示，间脑和脑干的摄取量很高，在120分钟时达到了峰值摄取量。（R，S）-西酞普兰的追踪研究。氢溴酸从所有富含SERT的大脑区域取代了[18F] 1放射性。使用DAT配体2β-羰基
• Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 and Fluorine-18 (<i>N</i>-Fluoroalkyl) Labeled 2β-Carbomethoxy-3β-(4'-(3-furyl)phenyl)tropanes and -nortropanes:  Candidate Radioligands for in Vivo Imaging of the Serotonin Transporter with Positron Emission Tomography
  作者：Jeffrey S. Stehouwer、Christophe Plisson、Nachwa Jarkas、Fanxing Zeng、Ronald J. Voll、Larry Williams、Laurent Martarello、John R. Votaw、Gilles Tamagnan、Mark M. Goodman

  DOI：10.1021/jm0504095

  日期：2005.11.1

  N-fluorobutyl (5) derivatives. The binding affinity for each compound to the human serotonin, dopamine, and norepinephrine transporters was determined using transfected HEK-293 cells. Radiolabeling and microPET brain imaging studies were performed with [(11)C]1, [(11)C]2, and [(18)F]3 to determine their utility as in vivo imaging agents.

  与N-甲基（2），N-氟乙基（3），N-氟丙基（4）和N-氟丁基（5）衍生物。使用转染的HEK-293细胞确定每种化合物对人血清素，多巴胺和去甲肾上腺素转运蛋白的结合亲和力。用[（11）C] 1，[（11）C] 2和[（18）F] 3进行了放射性标记和microPET脑成像研究，以确定它们作为体内成像剂的效用。
• Synthesis of a phenolic precursor and its efficient<i>O</i>-[¹⁸F]fluoroethylation with purified no-carrier-added [¹⁸F]2-fluoroethyl brosylate as the labeling agent
  作者：Nashwa Jarkas、Ronald J. Voll、Mark M. Goodman

  DOI：10.1002/jlcr.3046

  日期：2013.9

  [18F]2-Fluoroethyl-p-toluenesulfonate also called [18F]2-fluoroethyl tosylate has been widely used for labeling radioligands for positron emission tomography (PET). [18F]2-Fluoroethyl-4-bromobenzenesulfonate, also called [18F]2-fluoroethyl brosylate ([18F]F(CH2)2OBs), was used as an alternative radiolabeling agent to prepare [18F]FEOHOMADAM, a fluoroethoxy derivative of HOMADAM, by O-fluoroethylating the phenolic precursor. Purified by reverse-phase HPLC, the no-carrier-added [18F]F(CH2)2OBs was obtained in an average radiochemical yield (RCY) of 35%. The reaction of the purified and dried [18F]F(CH2)2OBs with the phenolic precursor was performed by heating in DMF and successfully produced [18F]FEOHOMADAM, after HPLC purification, in RCY of 21%. Copyright © 2013 John Wiley & Sons, Ltd.

  [18F]2-氟乙基对甲苯磺酸盐又称[18F]2-氟乙基对甲苯磺酸盐，已被广泛用于标记正电子发射断层扫描（PET）的放射性配体。[18F]2-氟乙基-4-溴苯磺酸盐，又称[18F]2-氟乙基对甲苯磺酸盐（[18F]F(CH2)2OBs），被用作一种替代放射性标记剂，通过对酚类前体进行 O-氟乙基化，制备出 HOMADAM 的氟乙氧基衍生物 [18F]FEOHOMADAM。通过反相高效液相色谱纯化，得到了无载体添加的[18F]F(CH2)2OBs，平均放射化学收率（RCY）为 35%。将纯化和干燥的[18F]F(CH2)2OBs 与酚类前体在 DMF 中加热反应，成功制得[18F]FEOHOMADAM，HPLC 纯化后的 RCY 为 21%。Copyright © 2013 John Wiley & Sons, Ltd. All Rights Reserved.
• Synthesis and evaluation of C-11, F-18 and I-125 small molecule radioligands for detecting oxytocin receptors
  作者：Aaron L. Smith、Sara M. Freeman、Jeffery S. Stehouwer、Kiyoshi Inoue、Ronald J. Voll、Larry J. Young、Mark M. Goodman

  DOI：10.1016/j.bmc.2012.02.019

  日期：2012.4

  Compounds 1-4 were synthesized and investigated for selectivity and potency for the oxytocin receptor (OTR) to determine their viability as radioactive ligands. Binding assays determined 1-4 to have high binding affinity for both the human and rodent OTR and also have high selectivity for the human OTR over human vasopressin V1a receptors (V1aR). Inadequate selectivity for OTR over V1aR was found for rodent receptors in all four compounds. The radioactive (C-11, F-18, and I-125) derivatives of 1-4 were synthesized and investigated for use as autoradiography and positron emission tomography (PET) ligands. Receptor autoradiography performed with [I-125]1 and [I-125]2 on rodent brain slices provided the first small molecule radioligand images of the OTR and V1aR. Biodistribution studies determined [I-125]1 and [I-125]2 were adequate for in vivo peripheral investigations, but not for central investigations due to low uptake within the brain. A biodistribution study with [F-18]3 suggested brain uptake occurred slowly over time. PET imaging studies with [F-18]3 and [C-11]4 using a rat model provided insufficient uptake in the brain over a 90 and 45 min scan times respectively to merit further investigations in non-human primates. (C) 2012 Elsevier Ltd. All rights reserved.