2-(1-{6-[(2-[¹⁸F]fluoroethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile | 259738-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-{6-[(2-[¹⁸F]fluoroethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile
• 英文别名: [¹⁸F]FDDNP；FDDNP；Fddnp F-18；2-[1-[6-[2-(18F)fluoranylethyl(methyl)amino]naphthalen-2-yl]ethylidene]propanedinitrile
• CAS: 259738-99-3
• 化学式: C₁₈H₁₆FN₃
• 分子量: 292.345
• InChiKey: IAVCEBMLYVGBLA-AWDFDDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(1-(6-[(2-(P-甲苯磺酰基氧基)乙基)(甲基)氨基]-2-萘基)亚乙基)丙二腈 在 fluorine-18 作用下， 生成 2-(1-{6-[(2-[¹⁸F]fluoroethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile
  参考文献：
  名称：

  Radiotracers for a multi-target approach to the diagnosis of Alzheimer's disease

  摘要：

  β-淀粉样蛋白斑块和神经纤维缠结是阿尔茨海默氏症（AD）的特征，会逐渐影响大脑的整体功能。非侵入性成像方法有助于早期诊断，将显著提高治疗的效果，并有可能预防阿尔茨海默氏症。我们报告了用于研究阿尔茨海默氏症的PET放射性示踪剂方法的发展，包括β-淀粉样蛋白斑块和缠结、烟碱α4β2受体、5-羟色胺5HT1A受体、多巴胺D2/D3受体和去甲肾上腺素转运体。目前，这种多靶点方法正在阿尔茨海默氏症转基因小鼠模型中进行评估。版权所有 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1266

文献信息

• Microfluidic Chemical Reaction Circuits
  申请人：Lee Cheng-Chung

  公开号：US20080281090A1

  公开（公告）日：2008-11-13

  New microfluidic devices, useful for carrying out chemical reactions, are provided. The devices are adapted for on-chip solvent exchange, chemical processes requiring multiple chemical reactions, and rapid concentration of reagents.

  提供了用于进行化学反应的新微流体器件。这些器件适用于芯片内的溶剂交换、需要多种化学反应的化学过程以及试剂的快速浓缩。
• Methods for binding agents to b-amyloid plaques
  申请人：Barrio R. Jorge

  公开号：US20070053831A1

  公开（公告）日：2007-03-08

  A method for labeling structures, such as β-amyloid plaques and neurofibrillary tangles, in vivo or in vitro, is provided and comprises contacting brain tissue with one or more compounds, preferably radiolabeled for detection by positron emission tomography (PET).

  提供了一种用于在体内或体外标记结构（如β-淀粉样斑块和神经原纤维缠结）的方法，包括将大脑组织与一个或多个化合物接触，最好是用正电子发射断层扫描（PET）检测的放射性标记。
• [EN] NON-POLAR AND POLAR LEAVING GROUPS<br/>[FR] GROUPES PARTANTS NON POLAIRES ET POLAIRES
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2011006610A1

  公开（公告）日：2011-01-20

  The present invention provides novel and advantageous processes for preparing and purifying pharmaceuticals The processes comprise a nucleophilic reaction wherein a modified leaving group LM, which has increased lipophilicity, of a vector in a nucleophilic reaction which offers a convenient and time-saving way to purify the product from non-reacted precursors vector-LM and by-products LM.

  本发明提供了一种新颖且有利的制备和纯化药物的方法。该方法包括一种亲核反应，其中使用了具有增加亲脂性的修饰离去基LM的载体，在亲核反应中，该载体提供了一种方便和省时的方式，以从未反应的前体载体-LM和副产物LM中纯化产物。
• NON-POLAR AND POLAR LEAVING GROUPS
  申请人：Graham Keith

  公开号：US20120238740A1

  公开（公告）日：2012-09-20

  The present invention provides novel and advantageous processes for preparing and purifying pharmaceuticals The processes comprise a nucleophilic reaction wherein a modified leaving group L M , which has increased lipophilicity, of a vector in a nucleophilic reaction which offers a convenient and time-saving way to purify the product from non-reacted precursors vector-L M and by-products L M .

  本发明提供了制备和纯化药物的新型和有利的过程。该过程包括一种亲核反应，其中向量中的具有增加亲脂性的改性离去基LM在亲核反应中作为一个方便和节省时间的方式，从未反应的前体向量-LM和副产物LM中纯化产物。
• Automated production of [¹⁸F]FDDNP using a TRACERlab MX_FDG
  作者：Johnny Vercouillie、Christian Prenant、Serge Maia、Patrick Emond、Stéphane Guillouet、Jean Bernard Deloye、Louisa Barré、Denis Guilloteau

  DOI：10.1002/jlcr.1745

  日期：——

  [18F]FDDNP has been recently described as a potent tracer to image amyloid plaques in vivo by positron emission tomography. Such a tool will be advisable to diagnose patient with mild cognitive impairment, to follow the disease progression and to evaluate new therapies. To make this radiopharmacetical affordable for the clinicians, we developed an automated method for [18F]FDDNP radiosynthesis using a commercial [18F]FDG unit. Radiolabeling with fluorine-18 was carried out by a [18F]fluoro-detosylation reaction on the precursor 2-(1-6-[(2-tosyloxyoethyl)(methyl)amino]-2-naphthyl}ethylidene)malononitrile. The reaction was performed in acetonitrile for 15 min at 90°C, and then the reaction mixture was injected into a semi-preparative high-pressure liquid chromatography. The desire [18F]FDDNP fraction was collected, and an SPE was performed. The [18F]FDDNP was formulated in a sodium chloride/ethanol solution followed by a sterile filtration. Stability of [18F]FDDNP was studied after 4 h and radiochemical purity of [18F]FDDNP remained >98%. The overall decay-corrected radiochemical yield was 15±3% (n=8). Radiochemical purity was >98% and the specific activity was 164±25 GBq/µmol at EOS. Pharmaceutical controls, bioburden, sterility, bacterial endotoxin and residual solvent tests were performed. The results were in accordance with the European Pharmacopoeia and demonstrated our ability to produce [18F]FDDNP with a pharmaceutical grade and a high reproducibility. Copyright © 2010 John Wiley & Sons, Ltd.

  [18F]FDDNP最近被描述为一种通过正电子发射断层扫描在体内成像淀粉样蛋白斑块的强效示踪剂。这种工具可用于诊断轻度认知障碍患者、跟踪疾病进展和评估新疗法。为了使临床医生能够负担得起这种放射性药物，我们开发了一种使用商用[18F]FDG装置进行[18F]FDDNP放射合成的自动化方法。通过在2-(1-6-[(2-甲苯磺酰氧乙基)(甲基)氨基]-2-萘基}亚乙基)丙二腈前体上进行[18F]氟脱甲烷化反应，进行氟-18的放射性标记。在90°C下在乙腈中反应15分钟，然后将反应混合物注入半制备型高压液相色谱仪。收集所需的[18F]FDDNP部分，并进行SPE。将[18F]FDDNP配制成氯化钠/乙醇溶液，然后进行无菌过滤。在4小时后研究了[18F]FDDNP的稳定性，[18F]FDDNP的放射化学纯度仍大于98%。总衰变校正后的放射化学产率为15±3%（n=8）。放射化学纯度大于98%，EOS时的比活度为164±25 GBq/µmol。进行了药物