[¹⁸F]-fluoromethyl triflate | 492450-24-5

• 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: [¹⁸F]-fluoromethyl triflate
• 英文别名: (18F)fluoranylmethyl trifluoromethanesulfonate
• CAS: 492450-24-5
• 化学式: C₂H₂F₄O₃S
• 分子量: 181.097
• InChiKey: QSSVYRPOXMPNLG-KTXUZGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  2
• 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：
  7

反应信息

• 作为反应物：
  描述：

  4,4'-bis-(1-methyl-3-hydroxy-morpholinyl-3)-biphenyl 、 [¹⁸F]-fluoromethyl triflate 以 丙酮 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Synthesis and biodistribution of new radiolabeled high-affinity choline transporter inhibitors [11C]hemicholinium-3 and [18F]hemicholinium-3

  摘要：

  The high-affinity choline transporter (CHT1) system is an attractive target for the development of positron emission tomography (PET) biomarkers to probe brain, cardiac, and cancer diseases. An efficient and convenient synthesis of new radiolabeled CHT1 inhibitors [C-11]hemicholinium-3 and [F-18]hemicholinium-3 by solid-phase extraction (SPE) technique using a cation-exchange CM Sep-Pak cartridge has been well developed. The preliminary evaluation of both tracers through biodistribution studies in 9L-glioma rats has been performed, and the uptakes in the heart and tumor were observed, while very low brain uptake was seen. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.105
• 作为产物：
  描述：

  silver trifluoromethanesulfonate 、 [18F]fluoromethyl bromide 生成 [¹⁸F]-fluoromethyl triflate
  参考文献：
  名称：

  N-甲基-d-天门冬氨酸受体离子通道的高亲和力配体的合成，结构活性关系，放射性标记和临床前评估，可作为正电子发射断层扫描的潜在成像探针

  摘要：

  所述Ñ甲基d天冬氨酸受体（NMDAR）参与许多神经障碍和精神障碍，包括阿尔茨海默氏病和精神分裂症。目前，尚无法评估体内NMDAr的可用性。这项研究的目的是为NMDAr离子通道开发正电子发射断层扫描（PET）配体。合成了一系列二-和三-N-取代的二芳基胍。此外，评估了大鼠前脑膜部分中NMDAr离子通道的体外结合亲和力。化合物10，11和32与任一碳-11或氟-18放射性标记物。配体[ 11 C] 10和[ 18F] 32在B6C3小鼠中进行了离体评估。生物分布研究表明，与小脑相比，前脑区域对[ 11 C] 10和[ 18 F] 32的吸收更高。另外，对于[ 11 C] 10 54％和[ 18 F] 32，在60分钟时大脑中70％的活动归因于完整的示踪剂。用MK-801（0.6 mg·kg -1，ip）进行的预处理稍微降低了NMDAr特定区域对[ 18 F] 32的吸收，但没有降低[ 11 C]

  DOI：

  10.1016/j.bmc.2014.12.029

文献信息

• Synthesis, structure activity relationship, radiolabeling and preclinical evaluation of high affinity ligands for the ion channel of the N-methyl-d-aspartate receptor as potential imaging probes for positron emission tomography
  作者：Pieter J. Klein、Johannes A.M. Christiaans、Athanasios Metaxas、Robert C. Schuit、Adriaan A. Lammertsma、Bart N.M. van Berckel、Albert D. Windhorst

  DOI：10.1016/j.bmc.2014.12.029

  日期：2015.3

  The N-methyl-d-aspartate receptor (NMDAr) is involved in many neurological and psychiatric disorders including Alzheimer’s disease and schizophrenia. Currently, it is not possible to assess NMDAr availability in vivo. The purpose of this study was to develop a positron emission tomography (PET) ligand for the NMDAr ion channel. A series of di- and tri-N-substituted diarylguanidines was synthesized

  所述Ñ甲基d天冬氨酸受体（NMDAR）参与许多神经障碍和精神障碍，包括阿尔茨海默氏病和精神分裂症。目前，尚无法评估体内NMDAr的可用性。这项研究的目的是为NMDAr离子通道开发正电子发射断层扫描（PET）配体。合成了一系列二-和三-N-取代的二芳基胍。此外，评估了大鼠前脑膜部分中NMDAr离子通道的体外结合亲和力。化合物10，11和32与任一碳-11或氟-18放射性标记物。配体[ 11 C] 10和[ 18F] 32在B6C3小鼠中进行了离体评估。生物分布研究表明，与小脑相比，前脑区域对[ 11 C] 10和[ 18 F] 32的吸收更高。另外，对于[ 11 C] 10 54％和[ 18 F] 32，在60分钟时大脑中70％的活动归因于完整的示踪剂。用MK-801（0.6 mg·kg -1，ip）进行的预处理稍微降低了NMDAr特定区域对[ 18 F] 32的吸收，但没有降低[ 11 C]
• [EN] N,N-SUBSTITUTED GUANIDINE COMPOUND<br/>[FR] COMPOSÉ DE GUANIDINE N,N-SUBSTITUÉE
  申请人：VERENIGING VOOR CHRISTELIJK HOGER ONDERWIJS WETENSCHAPPELIJK ONDERZOEK EN PATIENTENZORG

  公开号：WO2012165956A1

  公开（公告）日：2012-12-06

  The invention is directed to a N, N-substituted guanidine compound or a salt or solvate thereof according to formula (1), R1RNC(NH)NR2R3, wherein R1 is methyl and R2 is hydrogen. R3 is a organic group comprising a halogen and thiomethyl substituted phenyl group. R is an organic group comprising a substituted aryl group Z wherein the substituent group is -Y-R4, wherein Y is a heteroatom chosen from the group consisting of O, S and N and R4 is a fluorinated organic group.

  该发明涉及一种N，N-取代胍啶化合物或其盐或溶剂化合物，其化学式为（1），R1RNC（NH）NR2R3，其中R1为甲基，R2为氢。R3是一个包含卤素和硫甲基取代苯基的有机基团。R是一个包含取代芳基Z的有机基团，其中取代基团为-Y-R4，其中Y是从O、S和N组成的杂原子，R4是氟化有机基团。
• [EN] PYRIDYLACETYLENES FOR USE AS RADIOTRACERS AND IMAGING AGENTS<br/>[FR] PYRIDYLACETYLENES A UTILISER COMME RADIO-INDICATEURS ET AGENTS D'IMAGERIE
  申请人：NOVARTIS AG

  公开号：WO2005030723A1

  公开（公告）日：2005-04-07

  The present invention relates to novel pyridylacetylene derivatives of formula I, their Preparation, their use as radiotracers/markers and compositions containing them.

  本发明涉及一种新型的具有化学式I的吡啶基乙炔衍生物，其制备方法，作为放射示踪剂/标记物的用途以及含有它们的组合物。
• Radiosynthesis ofO-[11C]methyl-L-tyrosine andO-[18F]Fluoromethyl-L-tyrosine as potential PET tracers for imaging amino acid transport
  作者：Ren Iwata、Shozo Furumoto、Claudio Pascali、Anna Bogni、Kiichi Ishiwata

  DOI：10.1002/jlcr.696

  日期：2003.5

  Two positron-emitting analogues of tyrosine, O-[11C]methyl-L-tyrosine and O-[18F]fluoromethyl-L-tyrosine were prepared as new tumor imaging agents. The alkylating agent, [11C]methyl triflate or [18F]fluoromethyl triflate, was simply bubbled through a dimethylsulfoxide solution of L-tyrosine disodium salt at room temperature. After subsequent HPLC purification the labeled L-tyrosine analogues were obtained in decay-corrected radiochemical yields of over 50%, based on their corresponding labeling agent, with radiochemical purities always higher than 98%. The quite straightforward preparation, together with the high radiochemical yields achieved, make both these syntheses suitable for routine production. Copyright © 2003 John Wiley & Sons, Ltd.

  我们制备了两种可发射正电子的酪氨酸类似物--O-[11C]甲基-L-酪氨酸和 O-[18F]氟甲基-L-酪氨酸，作为新型肿瘤成像剂。只需在室温下将烷化剂--[11C]三氟甲基或[18F]氟甲基三氟甲基--气泡通过 L-酪氨酸二钠盐的二甲基亚砜溶液。经过随后的高效液相色谱纯化后，根据相应的标记剂，标记的 L- 酪氨酸类似物的衰变校正放射化学收率超过 50%，放射化学纯度始终高于 98%。这两种合成方法的制备非常简单，而且放射化学收率高，因此适合常规生产。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.
• ¹¹C- and¹⁸F-Labeled Radioligands for P-Glycoprotein Imaging by Positron Emission Tomography
  作者：Mariangela Cantore、Marcel Benadiba、Philip H. Elsinga、Chantal Kwizera、Rudi A. J. O. Dierckx、Nicola Antonio Colabufo、Gert Luurtsema

  DOI：10.1002/cmdc.201500420

  日期：2016.1

  AbstractP‐Glycoprotein (P‐gp) is an efflux transporter widely expressed at the human blood–brain barrier. It is involved in xenobiotics efflux and in onset and progression of neurodegenerative disorders. For these reasons, there is great interest in the assessment of P‐gp expression and function by noninvasive techniques such as positron emission tomography (PET). Three radiolabeled aryloxazole derivatives: 2‐[2‐(2‐methyl‐(11C)‐5‐methoxyphenyl)oxazol‐4‐ylmethyl]‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline ([11C]‐5); 2‐[2‐(2‐fluoromethyl‐(18F)‐5‐methoxyphenyl)oxazol‐4‐ylmethyl]‐6,7‐dimethoxy‐1,2,3,4‐tetra‐hydroisoquinoline ([18F]‐6); and 2‐[2‐(2‐fluoroethyl‐(18F)‐5‐methoxyphenyl)oxazol‐4‐ylmethyl]‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline ([18F]‐7), were tested in several in vitro biological assays to assess the effect of the aryl substituent in terms of potency and mechanism of action toward P‐gp. Methyl derivative [11C]‐5 is a potent P‐gp substrate, whereas the corresponding fluoroethyl derivative [18F]‐7 is a P‐gp inhibitor. Fluoromethyl compound [18F]‐6 is classified as a non‐transported P‐gp substrate, because its efflux increases after cyclosporine A modulation. These studies revealed a promising substrate and inhibitor, [11C]‐5 and [18F]‐7, respectively, for in vivo imaging of P‐gp by using PET.