2-[18F]fluoroethylamine | 199734-64-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2-[18F]fluoroethylamine
• 英文别名: [¹⁸F]2-fluoroethylamine；¹⁸F-fluoroethylamine；2-(18F)fluoranylethanamine
• CAS: 199734-64-0
• 化学式: C₂H₆FN
• 分子量: 62.0763
• InChiKey: FURHRJBOFNDYTG-KTXUZGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  4
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2',3'-isopropylideneadenosine-5'-carboxylic acid 、 2-[18F]fluoroethylamine 在 吡啶 、 N,N'-二异丙基碳二亚胺 作用下， 反应 0.67h， 以94%的产率得到5'-N-(2-[18F]fluoroethyl)-2',3'-O-isopropylidene-carboxamidoadenosine
  参考文献：
  名称：

  Synthesis of 5?-N-(2-[18F]fluoroethyl)-carboxamidoadenosine: a promising tracer for investigation of adenosine receptor system by PET technique

  摘要：

  5'-N-(2-[F-18]Fluoroethyl)-carboxamidoadenosine ([F-18]FNECA), a promising F-18-labelled adenosine agonist has been prepared by two different synthetic routes. In the first, [F-18]fluoride was reacted with 5'-N,N-ethylene-2',3'-O-isopropylidenecarboxamido-adenosine and after removing the protective group [F-18]FNECA was obtained in a low radiochemical yield (1+/-1%, mean+/-sd, n=7, decay corrected). In the second, 2-[F-18]fluoroethylamine was synthesised according to the literature and reacted with 2',3'-O-isopropylideneadenosine-5'-uronic acid in the presence of a coupling agent. The following hydrolysis step provided the [F-18]FNECA with a modest radiochemical yield (24+/-9%, n=17, based on [F-18]fluoride-activity). After purification by preparative reverse phase HPLC 18.9-166.5 MBq (0.51-4.5 mCi) [F-18]FNECA was obtained with a specific activity of 2.35+/-1.14 TBq/mmol (63.5+/-30.9 Ci/mmol, n=3). The total synthesis took 200 min and the decay corrected radiochemical yield based on [F-18]F- activity was 17+/-9% (n=5) with more than 99.9% radiochemical purity. This second route provides sufficient [F-18]FNECA for the subsequent biological evaluation using PET-technique.

  DOI：

  10.1002/1099-1344(200007)43:8<807::aid-jlcr365>3.0.co;2-k
• 作为产物：
  描述：

  2-[18F]fluoroethylazide 在 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 2-[18F]fluoroethylamine
  参考文献：
  名称：

  通过施陶丁格还原方便地获得 18F 标记胺

  摘要：

  Fluorine-18 在正电子发射断层扫描 (PET) 成像中具有出色的衰变特性。因此，它非常适合临床应用。因此，改进将氟-18纳入生物活性分子的策略至关重要。使用氨基功能化合成子进行间接 18F 标记是合成各种 PET 示踪剂的一种方便且通用的方法。在此，我们报告了一种通过施陶丁格还原将 18F 标记的叠氮化物转化为伯胺的方法。脂肪族和芳香族18F标记的叠氮化物被转化为相应的胺，转化率很高。该方法很容易实现自动化。从更广泛的角度来看，所应用的策略从单个前体产生两个有用的合成子，从而增加了以最少的合成工作标记不同化学支架的灵活性。

  DOI：

  10.1002/ejoc.201801457

文献信息

• Radiosynthesis of [¹⁸F]ATPFU: a potential PET ligand for mTOR
  作者：Vattoly J. Majo、Norman R. Simpson、Jaya Prabhakaran、J. John Mann、J. S. Dileep Kumar

  DOI：10.1002/jlcr.3239

  日期：2014.11

  achieved from beta-chloroaldehyde 3 in 4 and 5 steps, respectively, with an overall yield of 25-28%. [(18)F]Fluoroethylamine was prepared by heating N-[2-(toluene-4-sulfonyloxy)ethyl]phthalimide with [(18)F]fluoride ion in acetonitrile. [(18)F]1 was obtained by slow distillation under argon of [(18) F]FCH2CH2NH2 into amine 10 that was pre-treated with triphosgene at 0-5 °C. The total time required for

  哺乳动物雷帕霉素靶蛋白 (mTOR) 在细胞增殖的许多方面起着关键作用，最近的证据表明，改变的 mTOR 信号通路在衰老、肿瘤进展、神经精神疾病和重度抑郁症的发病机制中起着核心作用。mTOR 特异性 PET 示踪剂的可用性将有助于监测对临床开发中的 mTOR 抑制剂治疗的早期反应。为此，我们开发了 [(18)F]1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(2,2,2) -三氟乙基)-1H-吡唑并[3,4-d]嘧啶-6-基)苯基)-3-(2-氟乙基)脲[(18)F]ATPFU([(18)F]1)作为mTOR PET配体。参考文献 1 和放射性标记前体的合成，4-(4-8-oxa-3-azabicyclo[3.2.1]-octan-3yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazolo[3 ,4-d]嘧啶-6基）苯胺（10），分别通过
• Fluorous Synthesis of¹⁸F Radiotracers with the [¹⁸F]Fluoride Ion: Nucleophilic Fluorination as the Detagging Process
  作者：Romain Bejot、Thomas Fowler、Laurence Carroll、Sophie Boldon、Jane E. Moore、Jérôme Declerck、Véronique Gouverneur

  DOI：10.1002/anie.200803897

  日期：2009.1.5

  Tag team: The fluoro‐detagging of fluorous sulfonates by the [18F]fluoride ion was found to be an advantageous strategy for the preparation of various 18F‐labeled prosthetic groups and known radiotracers (see picture). Fluorous solid phase extraction (FSPE) was used to separate the excess fluorous precursor from the labeled material, which suggests that traditional purification protocols such as distillation

  标签小组：发现[ 18 F]氟离子对氟代磺酸盐进行氟脱标记是制备各种18 F标记的修复基团和已知放射性示踪剂的有利策略（参见图片）。荧光固相萃取（FSPE）用于从标记的材料中分离出过量的氟前体，这表明可以避免传统的纯化方案，例如蒸馏或繁琐的分离。
• Fluorine-18 labeled rhodamine derivatives for imaging with positron emission tomography
  申请人：Packard Alan B.

  公开号：US09101673B2

  公开（公告）日：2015-08-11

  The present invention is directed toward novel fluorine-18 labeled rhodamine dye derivatives and methods of making the same. The present invention is also directed toward methods of using novel fluorine-18 labeled rhodamine dye derivatives as positron emission tomography imaging agents and myocardial perfusion imaging agents.

  本发明涉及新型的氟-18标记若丹明染料衍生物及其制备方法。本发明还涉及使用新型氟-18标记若丹明染料衍生物作为正电子发射断层扫描成像剂和心肌灌注成像剂的方法。
• [EN] HETEROCYCLIC COMPOUNDS AS IMAGING PROBES OF TAU PATHOLOGY<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILISÉS COMME SONDES D'IMAGERIE DE PATHOLOGIE TAU
  申请人：GE HEALTHCARE LTD

  公开号：WO2013090497A1

  公开（公告）日：2013-06-20

  Pyridazinone compounds of Formula I: (I) wherein: R' is alkyl or Ar, optionally substituted with at least one alkyl, halo¬ gen, hydroxyl, alkoxy, haloalkoxy, acid, ester, amino, nitro, amide, or alkoxyhalo; 2 R is independently alkyi, alkynyl, ester, amino, amide, acid, aryl, heteroaryl, aminoalkyl, -C(=0)alkyl, -C(=0)aryl, -C(=0)heteroaryl, -C(=0)heterocycloalkyl, - C(=0)heterocycloalkylAr, -C(=0)(CH2)nhalo, -C(=0)(CH2)nheterocyclyl, or -SC^Ar, optionally substituted with at least one alkyi, alkylhalo, halogen, nitro, aryl, heteroaryl, or heteroaryl(CH2)nhalo; R 3 and R4 are independently hydrogen, alkyi, alkenyl, alkynyl, aryl, heteroaryl; Ar is an aryl, heteroaryl, cycloalkyl, heterocycloalkyl group; n is an integer from 0-10; or a radiolabeled derivative thereof. The compounds are useful as imaging probes of Tau pathology in Alzheimer's disease are described. Compositions and methods of making such compounds are also described.

  Formula I中的吡啶嗪酮化合物：（I），其中：R'是烷基或Ar，可选择地取代为至少一个烷基，卤素，羟基，烷氧基，卤代烷氧基，酸，酯，氨基，硝基，酰胺，或烷氧基卤代；2 R独立地是烷基，炔基，酯，氨基，酰胺，酸，芳基，杂环芳基，氨基烷基，-C(=0)烷基，-C(=0)芳基，-C(=0)杂环芳基，-C(=0)杂环烷基，-C(=0)杂环烷基Ar，-C(=0)(CH2)n卤代，-C(=0)(CH2)n杂环基，或-SC^Ar，可选择地取代为至少一个烷基，烷基卤代，卤素，硝基，芳基，杂环芳基，或杂环芳基(CH2)n卤代；R3和R4独立地是氢，烷基，烯基，炔基，芳基，杂环芳基；Ar是芳基，杂环芳基，环烷基，杂环烷基基团；n是0-10之间的整数；或其放射标记衍生物。所述化合物可用作阿尔茨海默病中Tau病理的成像探针。还描述了制备这种化合物的组成物和方法。
• Synthesis of 10,11,14,15-13C4-and 14,15-13C2-retinyl acetate
  作者：Sherry A. Tanumihardjo

  DOI：10.1002/jlcr.464

  日期：2001.4

  The synthesis of 10,11,14,15-13C4- and 14,15-13C2-retinyl acetate is described. The procedure uses a modified Wittig-Horner synthesis. By using the 13C isotope, sensitive gas chromatography-combustion-isotope ratio mass spectrometry can be used for analysis in application to human isotope dilution studies. Copyright © 2001 John Wiley & Sons, Ltd.

  本文介绍了 10,11,14,15-13C4- 和 14,15-13C2- 视黄醇乙酸酯的合成。该过程采用改良的维蒂希-霍纳合成法。通过使用 13C 同位素，灵敏的气相色谱-燃烧-同位素比质谱法可用于人体同位素稀释研究的分析。Copyright © 2001 John Wiley & Sons, Ltd. All Rights Reserved.