1-azido-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)ethane | 1233816-91-5

• 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: 1-azido-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)ethane
• 英文别名: Azido-PEG3-flouride；1-azido-2-[2-[2-(2-fluoroethoxy)ethoxy]ethoxy]ethane
• CAS: 1233816-91-5
• 化学式: C₈H₁₆FN₃O₃
• 分子量: 221.232
• InChiKey: PAFRRASHGCWMIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-azido-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)ethane 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)ethan-1-amine
  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
• 作为产物：
  描述：

  11-叠氮基-3,6,9-三氧杂十一醇 在 四丁基氟化铵 、 三乙胺 作用下， 以 2-甲基-2-丁醇 、 二氯甲烷 、 水 为溶剂， 反应 13.0h， 生成 1-azido-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)ethane
  参考文献：
  名称：

  Novel multifunctional 18F-labelled PET tracer with prostate-specific membrane antigen-targeting and hypoxia-sensitive moieties

  摘要：

  Prostate cancer is one of the most frequently found cancers in men worldwide. Prostate-specific membrane antigen (PSMA) is typically highly expressed in prostate cancer, and the Glu-Urea-Lys (GUL) structure has recently received considerable attention as a key unit of PSMA-targeting agents. Additionally, one of the common characteristics of many solid tumors, such as prostate cancer, is hypoxia. In this study, novel multifunctional PSMA inhibitors containing a PSMA-targeting moiety either with or without a hypoxia-sensitive moiety (F-18-PEG(3)-ADIBOT-2NI-GUL and F-18-PEGS-ADIBOT-GUL, respectively; ADIBOT: azadibenzocyclooctatriazole, 2N1: 2-nitroimidazole) were designed and synthesized, and their feasibility as PET tracers for prostate cancer imaging studies was examined. The compounds labelled with F-18 via the copper-free click reaction were stable in human serum and showed nanomolar binding affinities in in vitro PSMA binding assays. Micro-PET and biodistribution studies indicate that both F-18-labelled inhibitors successfully accumulated in prostate cancer regions, and F-18-PEGS-ADIBOT-2NI-GUL showed a 2-fold higher tumor-to-total non-target organ ratio than that of F-18-PEGS-ADIBOT-GUL, suggesting that the synergistic effects of the PSMA-targeting GUL moiety and the hypoxia-sensitive 2-nitroimidazole moiety can increase tumor uptake of the novel PET tracers in prostate cancer. These findings suggest that this novel multifunctional PET tracer with an F-18-labelled PSMA inhibitor and a 2-nitroimidazole moiety is a potent candidate to provide better diagnosis of prostate cancer via PET imaging studies. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112099

文献信息

• [EN] THERAPEUTIC AGENT FOR TREATING TUMORS<br/>[FR] AGENT THÉRAPEUTIQUE POUR LE TRAITEMENT DE TUMEURS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2015143092A1

  公开（公告）日：2015-09-24

  The present disclosure relates to a therapeutic agent of the formula: Z-C(=O)-(CH2)n-ϕ-S-S-(CRR')m-(CH2)p-C(=O)- NH-(CH2)q-NH-Y[NH-(CH2)r-X-T-W][NH-(CH2-CH-O)t (CH2)s-NH-V] Formula I or a pharmaceutically acceptable salt thereof, useful for treating tumors, including cancers. Where the compound of Formula I also contains a radionuclide or an imaging agent or both, the compound of formula I is a theranostic agent useful for treating and diagnosing tumors, including cancers.

  本公开涉及一种治疗剂，其化学式为：Z-C(=O)-(CH2)n-ϕ-S-S-(CRR')m-( )p-C(=O)- NH-( )q-NH-Y[NH-( )r-X-T-W][NH-( -CH-O)t ( )s-NH-V] 化学式I或其药学上可接受的盐，用于治疗肿瘤，包括癌症。化合物I的化学式还包含放射性核素或成像剂或两者的情况下，化合物I是一种治疗和诊断肿瘤，包括癌症的治疗剂。
• Radiofluorinated Pyrimidine-2,4,6-triones as Molecular Probes for Noninvasive MMP-Targeted Imaging
  作者：Hans-Jörg Breyholz、Stefan Wagner、Andreas Faust、Burkhard Riemann、Carsten Höltke、Sven Hermann、Otmar Schober、Michael Schäfers、Klaus Kopka

  DOI：10.1002/cmdc.201000013

  日期：2010.5.3

  biological targets for the specific visualization of such pathologies, in particular by using radiolabeled MMP inhibitors (MMPIs). The aim of this work was to develop a radiofluorinated molecular probe for noninvasive in vivo imaging for the detection of up‐regulated levels of activated MMPs in the living organism. Fluorinated MMPIs (26, 31 and 38) based on the pyrimidine‐2,4,6‐trione lead structure

  基质金属蛋白酶（MMP）是依赖锌和钙的内肽酶。代表甲氧西林超家族的一个亚家族，MMP参与细胞外基质成分的蛋白水解降解。MMP表达失调，MMP失调和MMP活性局部升高是各种疾病（例如癌症，动脉粥样硬化，中风，关节炎等）的共同特征。因此，活化的MMP是用于这种病理学的具体可视化的合适的生物学靶标，特别是通过使用放射性标记的MMP抑制剂（MMPI）。这项工作的目的是开发一种用于非侵入性体内成像的放射性氟化分子探针，用于检测活生物体中活化的MMP的上调水平。氟化的MMPi（26，31和38）基于嘧啶-2,4,6-三酮铅结构合成了RO 28-2653（1），并在体外评估了其对MMP的抑制力。实现了第一个18 F标记的原型MMP靶向示踪剂[ 18 F] 26的放射性合成和体内生物分布，该原型适合通过正电子发射断层扫描（PET）进行分子成像。
• CASPASE-3-TRIGGERED MOLECULAR SELF-ASSEMBLING PET PROBES AND USES THEREOF
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200085980A1

  公开（公告）日：2020-03-19

  Embodiments of the synthesis, radiolabeling and biological applications of an activatable tracer that undergoes intramolecular cyclization and aggregation upon activation by cleavage of a blocking moiety are provided. The probes of the disclosure allow for target-controlled self-assembly of small molecules in living subjects for imaging and drug delivery. The aggregated nanoprobes of the disclosure may be detectable optically, by PET detection, magnetic resonance imaging, and the like depending on the detectable reporter attached to the nanoprobe.

  提供了一种可激活示踪剂的合成、放射标记和生物应用的实施例，该示踪剂在通过切除阻断基团激活时发生分子内环化和聚集。本公开的探针允许在活体中实现靶向控制的小分子自组装，用于成像和药物输送。根据附加到纳米探针上的可检测报告物，本公开的聚集纳米探针可以通过光学、PET检测、核磁共振成像等方式进行检测。
• [EN] COMPOUNDS WITH MATRIX-METALLOPROTEINASE INHIBITORY ACTIVITY<br/>[FR] COMPOSÉS AVEC ACTIVITÉ INHIBITRICE DE MÉTALLOPROTÉINASE DE MATRICE
  申请人：UNIV MUENSTER

  公开号：WO2013010573A1

  公开（公告）日：2013-01-24

  The present invention relates to the field of therapeutic and diagnostic agents and more specifically to compounds of formula (I) that are inhibitors of matrix-metalloproteinases (MMPs) and are useful in the treatment of diseases related thereto such as cardiovascular diseases, inflammatory diseases and malignant diseases. One embodiment of the invention is a compound of formula (I) labeled with a 18-fluorine atom having matrix metalloproteinase inhibitory activity suitable for diagnostic imaging. Also disclosed in the present invention is a pharmaceutical composition comprising the inhibitors of matrix-metalloproteinases (MMPs) of the invention or the corresponding labeled compounds useful as diagnostic imaging agents of the invention in a form suitable for mammalian administration. The invention furthermore discloses intermediates in the synthesis of the inhibitors of matrix-metalloproteinases (MMPs) of the invention and of the diagnostic imaging agents of the invention.

  本发明涉及治疗和诊断试剂领域，更具体地涉及一种具有式（I）的化合物，该化合物是基质金属蛋白酶（MMPs）的抑制剂，并且在治疗与之相关的疾病如心血管疾病、炎症性疾病和恶性疾病方面有用。本发明的一个实施例是一种带有18-氟原子的式（I）化合物，具有适用于诊断成像的基质金属蛋白酶抑制活性。本发明还公开了一种包含本发明的基质金属蛋白酶（MMPs）抑制剂或相应标记化合物的制药组合物，适合于哺乳动物管理。此外，本发明还公开了在合成本发明的基质金属蛋白酶（MMPs）抑制剂和诊断成像剂中的中间体。
• 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。