18F-acetyl hypofluorite | 84243-94-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 18F-acetyl hypofluorite
• 英文别名: acetyl [18F]hypofluorite；Fluoranyl acetate
• CAS: 84243-94-7
• 化学式: C₂H₃FO₂
• 分子量: 77.0446
• InChiKey: QWLICVXJMVMDDQ-KTXUZGJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  18F-acetyl hypofluorite 生成 [18F]-Fluorodeoxyglucose
  参考文献：
  名称：

  PADGETT, H. C.;SCHMIDT, D. G.;LUXEN, A.;BIDA, G. T.;SATYAMURTHY, N.;BARRI+, J. LABELL. COMPOUNDS AND RADIOPHARM., 26,(1989) C. 469-471

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium acetate 在 <18F>-fluorine 作用下， 生成 18F-acetyl hypofluorite
  参考文献：
  名称：

  Synthesis of 18F-labelled 2-deoxy-2-fluoro-d-galactopyranose using the acetyl hypofluorite procedure

  摘要：

  DOI：

  10.1016/s0008-6215(00)90089-2
• 作为试剂：
  描述：

  5-氯-8-羟基喹啉 在 18F-acetyl hypofluorite 作用下， 以 溶剂黄146 、 三氟乙酸 为溶剂， 生成 5-chloro-7-[18F]fluoro-8-hydroxyquinoline
  参考文献：
  名称：

  COMPOUNDS WHICH CAN BE USED TO DIAGNOSE AND MONITOR DISEASES ASSOCIATED WITH THE FORMATION OF AMYLOID PROTEIN FIBRILS

  摘要：

  公开号：

  EP1563852B1

文献信息

• Two-step regio- and stereoselective syntheses of [19F]- and [18F]-2-deoxy-2-(R)-fluoro-β-d-allose
  作者：Rezwan Ashique、Raman V. Chirakal、Donald W. Hughes、Gary J. Schrobilgen

  DOI：10.1016/j.carres.2005.12.002

  日期：2006.3

  Replacement of specific hydroxyl groups by fluorine in carbohydrates is an ongoing challenge from chemical, biological, and pharmaceutical points of view. A rapid and efficient two-step, regio- and stereoselective synthesis of 2-deoxy-2-(R)-fluoro-beta-d-allose (2-(R)-fluoro-2-deoxy-beta-d-allose; 2-FDbetaA), a fluorinated analogue of the rare sugar, d-allose, is described. TAG (3,4,6-tri-O-acetyl-1

  从化学，生物学和药学的观点来看，碳水化合物中的氟取代特定的羟基是一个持续的挑战。快速，有效的两步，区域和立体选择性合成2-deoxy-2-（R）-氟-β-d-阿洛糖（2-（R）-氟-2-脱氧-β-d-阿洛糖;描述了2-FDbeTAA），一种稀有糖的氟化类似物d-阿​​洛糖。TAG（3,4,6-三-O-乙酰基-1,5-脱水-2-脱氧-d-阿拉伯糖基己糖-1-烯醇或3,4,6-三-O-乙酰基-d-葡萄糖醛）将其在Ne / He混合物中与稀F（2）或与CH（3）COOF在-60°C下于无水HF中氟化。将氟化的中间体在1N HCl中水解，并将水解产物通过液相色谱法纯化并进行表征1D（1）H，（13）C和（19）F NMR光谱以及2D NMR光谱和质谱分析。此外，首次合成（18）F标记的2-deoxy-2-（R）-氟-β-d-阿洛糖（2-[（（18）F] FDbeTAA），经衰变校正后的总放射化学产率为相对于[（18）F]
• Synthesis and characterization of novel radiofluorinated probes for positron emission tomography imaging of monoamine oxidase B
  作者：Mitsuyoshi Yoshimoto、Masahiko Hirata、Shinya Kagawa、Yasuhiro Magata、Yoshiro Ohmomo、Takashi Temma

  DOI：10.1002/jlcr.3779

  日期：2019.7

  Monoamine oxidase B (MAO-B), predominantly expressed in glial cells, plays an important role in neurotransmitter regulation, and MAO-B activity relates to several neuronal diseases. Here, we aimed to develop a radiofluorinated MAO-B imaging probe based on the structure of a selective MAO-B inhibitor, MD-230254. We synthesized and evaluated a series of compounds in vitro and in vivo. A series of fluorinated analogs of MD-230254 were synthesized and evaluated for inhibitory potency and selectivity toward MAO-B. 5-[4-(2-[18F]Fluorobenzyloxy)phenyl]-3-(2-cyanoethyl)-1,3,4-oxadiazol-2(3H)-one (2-[18F]FBPO) was synthesized from a corresponding tributylstannyl precursor and [18F]CH3COOF. Biodistribution after intravenous injection of 2-[18F]FBPO was evaluated in male ddY mice with or without pretreatment by inhibitors. Among the compounds synthesized and evaluated, 2-FBPO showed high inhibitory potency and selectivity toward MAO-B comparable with MD-230254. 2-[18F]FBPO was successfully synthesized by an electrophilic reaction with a high radiochemical purity of more than 99%. 2-[18F]FBPO was efficiently taken up by the brain and showed rapid blood clearance, which provided a brain/blood radioactivity ratio of 3.7 at 90 minutes postinjection. The brain radioactivity was significantly decreased by pretreatment with an MAO-B selective inhibitor. The great potential of 2-[18F]FBPO as an MAO-B imaging probe, applicable to a variety of diseases, is indicated.

  单胺氧化酶 B（MAO-B）主要表达于神经胶质细胞，在神经递质调节中发挥着重要作用，MAO-B 的活性与多种神经元疾病有关。在此，我们旨在根据一种选择性 MAO-B 抑制剂 MD-230254 的结构开发一种放射性氟化 MAO-B 成像探针。我们合成并在体外和体内评估了一系列化合物。我们合成了一系列 MD-230254 的含氟类似物，并评估了它们对 MAO-B 的抑制效力和选择性。5-[4-(2-[18F]氟苄氧基)苯基]-3-(2-氰乙基)-1,3,4-恶二唑-2(3H)-酮（2-[18F]FBPO）由相应的三丁基锡前体和[18F]CH3COOF合成。评估了雄性 ddY 小鼠静脉注射 2-[18F]FBPO 后的生物分布情况，无论是否经过抑制剂预处理。在合成和评估的化合物中，2-FBPO 对 MAO-B 具有很高的抑制效力和选择性，可与 MD-230254 相媲美。通过亲电反应成功合成了 2-[18F]FBPO，其放射化学纯度高达 99% 以上。2-[18F]FBPO能被大脑有效吸收，并在血液中迅速清除，注射后90分钟的脑/血放射性比为3.7。在使用 MAO-B 选择性抑制剂预处理后，脑部放射性明显降低。2-[18F]FBPO作为一种MAO-B成像探针，适用于多种疾病，具有巨大的潜力。
• Synthesis and preliminary evaluation of [18F]2-deoxy-2,2-difluoro-glucose as a potential PET imaging agent
  作者：Michael J. Adam

  DOI：10.1002/(sici)1099-1344(199908)42:8<809::aid-jlcr241>3.0.co;2-8

  日期：1999.8
• Novel ¹⁸F-Labeled α-Methyl-Phenylalanine Derivative with High Tumor Accumulation and Ideal Pharmacokinetics for Tumor-Specific Imaging
  作者：Hirofumi Hanaoka、Yasuhiro Ohshima、Aiko Yamaguchi、Hiroyuki Suzuki、Noriko S. Ishioka、Tetsuya Higuchi、Yasushi Arano、Yoshito Tsushima

  DOI：10.1021/acs.molpharmaceut.9b00446

  日期：2019.8.5

  Positron emission tomography (PET) imaging with F-18-labeled alpha-methyl-substituted amino acids exerts significant influence on differential diagnosis of malignant tumors and tumor-like lesions. Exclusive uptake via L-type amino acid transporter 1 (LAT1), a tumor-specific transporter, accounts for their excellent tumor specificity and low background accumulation. However, further refinement and optimization in their tumor accumulation and pharmacokinetics are sorely needed. To address these issues, we newly designed F-18-labeled alpha-methyl-phenylalanine (F-18-FAMP) regioisomers (2-, 3-, or 4-F-18-FAMP) and stereoisomers (L- or D-form), and we comprehensively evaluated their potential as tumor-imaging agents. F-18-FAMPs were prepared from alpha-methyl phenylalanine by electrophilic radiofluorination and purified by reversed-phase HPLC. In biodistribution studies on normal mice, L-2-F-18-FAMP and the three D-F-18-FAMPs showed faster blood clearance and lower renal accumulation than L-3-F-18-FAMP or L-4-F-18-FAMP. In LS180 human colorectal cancer cell line xenograft mice, L-2-F-18-FAMP exhibited significantly higher tumor accumulation than the D-F-18-FAMPs or a clinically relevant tracer, L-3-F-18-alpha-methyl-tyrosine (F-18-FAMT) (p < 0.05). The renal accumulation levels of L-2-F-18-FAMP were significantly lower than that of F-18-FAMT (p < 0.01). LAT-1 specificity of L-2-F-18-FAMP was validated in the cellular uptake studies. The PET imaging with L-2-F-18-FAMP clearly visualized the tumor as early as 1 h after injection, and the high tumor accumulation level was retained for 3 h. These findings suggest that L-2-F-18-FAMP constitutes a potential PET tracer for tumor-specific imaging.
• STEINBACH, J.;BEYER, G. -J.;GUNTHER, K., ZENTRALINST. KERNFORSCH. ROSSENDORF DRESDEN <BER.>,(1988) N40, C. 19-22
  作者：STEINBACH, J.、BEYER, G. -J.、GUNTHER, K.

  DOI：——

  日期：——