¹⁸F-1-azido-2-(2-(2-fluoroethoxy)ethoxy)ethane | 1228754-75-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: ¹⁸F-1-azido-2-(2-(2-fluoroethoxy)ethoxy)ethane
• 英文别名: 2-(2-(2-[¹⁸F]fluoroethoxy)ethoxy)ethyl azide；1-azido-2-[2-(2-(18F)fluoranylethoxy)ethoxy]ethane
• CAS: 1228754-75-3
• 化学式: C₆H₁₂FN₃O₂
• 分子量: 176.18
• InChiKey: RKICXNDPAUCMST-JZRMKITLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ¹⁸F-1-azido-2-(2-(2-fluoroethoxy)ethoxy)ethane 、 在 [Cu(MeCN)₄PF₆] 、 bathophenantrolinedisulfonic acid disodium salt 作用下， 反应 0.08h， 以95%的产率得到(8S,9R,11S,13S,14S,17S)-11-(4-((17-(1-(2-(2-(2-fluoroethoxy)ethoxy)ethyl)-1H-1,2,3-triazol-4-yl)-3-methyl-6,9,12,15-tetraoxa-3-azaheptadecyl)oxy)phenyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  [EN] ESTROGEN RECEPTOR IMAGING AGENTS
  [FR] AGENTS D'IMAGERIE D'UN RÉCEPTEUR DES ŒSTROGÈNES

  摘要：

  提供了用于分子成像表达雌激素受体的细胞的化合物。还提供了用于制备这些化合物的中间体以及使用模块收敛策略制备这些化合物的方法。此外，描述了制备这些中间体的方法，以及使用这些化合物作为成像剂在受试者中诊断疾病的方法。

  公开号：

  WO2014093378A1
• 作为产物：
  描述：

  2-(2-(2-azidoethoxy)ethoxy)ethyl methanesulfonate 在 kryptofix 222 potassium methanesulfonate salt 、 氢氟酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以90%的产率得到¹⁸F-1-azido-2-(2-(2-fluoroethoxy)ethoxy)ethane
  参考文献：
  名称：

  불포화 탄화수소기를 갖는 알코올 용매를 이용한 플루오로 화합물의 제조방법

  摘要：

  本发明涉及有机氟化合物的制备，其中包括[18F]氟化物，通过使用被标记为化学式1的溶剂进行亲核氟化反应，不仅可以高产率地制备有机氟化合物，而且该溶剂对前体化合物的溶解度非常优越，适用于自动合成18F标记的放射性药物。

  公开号：

  KR102063498B1

文献信息

• 受体类分子靶向显像剂及其制备方法和应用
  申请人：厦门大学

  公开号：CN106632571B

  公开（公告）日：2018-12-07

  本发明公开了受体类分子靶向显像剂及其制备方法和应用，该显像剂具有一个聚乙二醇短链，通过“点击”反应与靶向雌激素受体的17α‑炔雌醇相连接，该显像剂具体结构通式如下：其中，17α‑炔雌醇作为靶向基团，聚乙二醇作为亲水基团，18F为放射性基团。该受体类分子靶向显像剂具有优良的生物性能，在雌激素受体阳性的乳腺癌肿瘤中具有较高的摄取,可以区分雌激素阳性受体和雌激素阴性受体，具有较强特异性，满足用作乳腺癌受体显像剂的条件。
• PROBE FOR IMAGING PARP-1 ACTIVITY
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20160185805A1

  公开（公告）日：2016-06-30

  Provided are embodiments of a small molecule tracer for positron emission tomography (PET) imaging of the enzyme activity of PARP-1 that is responsible for DNA-damage sensing and critically involved in radiation therapy and some chemotherapy response mechanisms. These PARP-1 tracers are derivatives of nicotinamide adenine dinucleotide (NAD), which is the natural substrate for PARP-1. Provided are NAD derivatives that include a linker moiety to which may be attached a label moiety such as a PET detectable fluorine to generate a 6N-(triazo-PEG2- 18 F)-NAD. Especially advantageous for use in PET and MRI scanning detection systems is the attachment of a chelating agent that allows for the formation of a chelator-metal ion complex.

  提供了一种用于正电子发射断层扫描（PET）成像PARP-1酶活性的小分子示踪剂的实施例，PARP-1酶负责DNA损伤感知，在放射治疗和一些化疗反应机制中起着关键作用。这些PARP-1示踪剂是烟酰胺腺嘌呤二核苷酸（NAD）的衍生物，NAD是PARP-1的天然底物。提供了包括连接基团的NAD衍生物，可以附加标记基团，如PET可检测的氟，以生成6N-(triazo-PEG2-18F)-NAD。尤其适用于PET和MRI扫描检测系统的是连接螯合剂的附着，允许形成螯合剂-金属离子复合物。
• Synthesis and evaluation of a 18F-curcumin derivate for β-amyloid plaque imaging
  作者：Johanna Rokka、Anniina Snellman、Cristiano Zona、Barbara La Ferla、Francesco Nicotra、Mario Salmona、Gianluigi Forloni、Merja Haaparanta-Solin、Juha O. Rinne、Olof Solin

  DOI：10.1016/j.bmc.2014.03.010

  日期：2014.5

  In vitro studies of [18F]4 with the transgenic APP23 mouse revealed high β-amyloid plaque binding. In vivo and ex vivo studies demonstrated that [18F]4 has fast clearance from the blood, moderate metabolism but low blood–brain barrier (BBB) penetration. Conclusions [18F]4 was synthesized in high yield and excellent quality. In vitro studies, metabolite profile, and fast clearance from the blood indicated

  介绍 姜黄素是一种神经保护性化合物，可抑制淀粉样蛋白低聚物和原纤维的形成，并与阿尔茨海默病（AD）中的β-淀粉样蛋白斑块结合。我们旨在合成18 F标记的姜黄素衍生物（[ 18 F] 4），并表征其在AD转基因APP23小鼠模型中的正电子发射断层扫描（PET）示踪剂与β-淀粉样蛋白斑块的结合特性。 方法 我们利用亲核的18 F氟化和点击化学，轻松地一锅合成[ 18 F] 4。使用针对PIB的异源竞争性结合，体外研究了转基因APP23小鼠脑冷冻切片中[ 18 F] 4与β-淀粉样蛋白斑的结合。[ 18 F] 4在啮齿类动物体内和体内的摄取研究使用转基因APP23和野生型对照小鼠的PET /计算机断层扫描技术进行。 结果 [ 18 F] 4的放射化学产率为21±11％，比活度超过1 TBq /μmol，合成结束时放射化学纯度超过99.3％。用转基因APP23小鼠对[ 18 F] 4进行的体外研究
• Radiosynthesis, biological evaluation and preliminary microPET study of 18F-labeled 5-resorcinolic triazolone derivative based on ganetespib targeting HSP90
  作者：Julie Kang、Jun Young Lee、İsa Taş、Kunal N. More、Hangun Kim、Jeong-Hoon Park、Dong-Jo Chang

  DOI：10.1016/j.bmcl.2018.10.035

  日期：2018.12

  Heat-shock protein 90 (HSP90) is a molecular chaperone that activates oncogenic transformation in several solid tumors, including lung and breast cancers. Ganetespib, a most promising candidate among several HSP90 inhibitors under clinical trials, has entered Phase III clinical trials for cancer therapy. Despite numerous evidences validating HSP90 as a target of anticancer, there are few studies on PET agents targeting oncogenic HSP90. In this study, we synthesized and biologically evaluated a novel F-18-labeled 5-resorcinolic triazolone derivative (1, [F-18]PTP-Ganetespib) based on ganetespib. [F-18]PTP-Ganetespib was labeled by click chemistry of Ganetespib-PEG-Alkyne (10) and [F-18]PEG-N-3 (11) with 37.3 +/- 5.11% of radiochemical yield and 99.7 +/- 0.09% of radiochemical purity. [F-18]PTP-Ganetespib showed proper LogP (0.96 +/- 0.06) and good stability in human serum over 97% for 2 h. [F-18]PTP-Ganetespib showed high uptakes in breast cancer cells containing triple negative breast cancer (TNBC) MDA-MB-231 and Her2-negative MCF-7 cells, which are target breast cancer cell lines of HSP90 inhibitor, ganetespib, as an anticancer. Blocking of HSP90 by the pretreatment of ganetespib exhibited significantly decreased accumulation of [F-18]PTP-Ganetespib in MDA-MB-231 and MCF-7 cells, indicating the specific binding of [F-18]PTP-Ganetespib to MDA-MB-231 and MCF-7 cells with high HSP90 expression. In the biodistribution and microPET imaging studies, the initial uptake into tumor was weaker than in other thoracic and abdominal organs, but [F-18]PTP-Ganetespib was retained relatively longer in the tumor than other organs. The uptake of [F-18]PTP-Ganetespib in tumors was not sufficient for further development as a tumor-specific PET imaging agent by itself, but this preliminary PET imaging study of [F-18]PTP-Ganetespib can be basis for developing new PET imaging agents based on HSP90 inhibitor, ganetespib.
• 18F-LABELLED COMPOUND FOR PROSTATE CANCER DIAGNOSIS, AND USE THEREOF
  申请人：Futurechem Co., Ltd.

  公开号：EP3643707B1

  公开（公告）日：2022-02-23