氟甲氧甲基硝基咪唑乙醇 | 13551-89-8

• 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
• 中文名称: 氟甲氧甲基硝基咪唑乙醇
• 中文别名: 1H-咪唑-1-乙醇；1-氟-3-(2-硝基-咪唑-1-基)-2-丙醇
• 英文名称: Fluoromisonidazole
• 英文别名: 1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol；1-(3-fluoro-2-hydroxypropyl)-2-nitroimidazole；1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-ol；FMISO；F-MISO
• CAS: 13551-89-8
• 化学式: C₆H₈FN₃O₃
• mdl: MFCD01319115
• 分子量: 189.146
• InChiKey: HIIJZYSUEJYLMX-UHFFFAOYSA-N

物化性质

• 沸点：
  433.3±55.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为产物：
  描述：

  1-(3-fluoro-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-2-nitro-1H-imidazole 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以55%的产率得到氟甲氧甲基硝基咪唑乙醇
  参考文献：
  名称：

  Preliminary research on 1-(4-bromo-2-nitroimidazol-1-yl)-3-[ 18 F]fluoropropan-2-ol as a novel brain hypoxia PET tracer in a rodent model of stroke

  摘要：

  The synthesis of the new radiotracer precursor 4-Br-NITTP and the radiolabeling of the new tracer 1-(4-bromo-2-nitroimidazol-1-yl)-3-[F-18]fluoropropan-2-ol (4-Br-[F-18]FMISO) is reported. The cyclic voltammetry behaviour, neuronal cell toxicity, transport through the brain endothelial cell monolayer, in vivo PET imaging and preliminary calculations of the tracer uptake for a rodent model of stroke were studied for the new compound and the results were compared to those obtained with [F-18]FMISO, the current gold standard PET hypoxia tracer. The new PET brain hypoxia tracer is more easily reduced, has higher ClogP than [F-18]FMISO and it diffuses more rapidly through brain endothelial cells. The new compound is non-toxic to neuronal cells and it allows the in vivo mapping of stroke in mice with higher sensitivity. 4-Br-[F-18]FMISO is a good candidate for further development in ischemic stroke. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.023

文献信息

• [EN] NITROIMIDAZOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE NITROIMIDAZOLE
  申请人：GE HEALTHCARE LTD

  公开号：WO2011151320A1

  公开（公告）日：2011-12-08

  The present invention provides novel compounds useful in the treatment and diagnosis of mycobacterial infections. Compounds of the present invention have enhanced biological properties as compared to the related known compounds. The present invention also provides a precursor compound useful in the synthesis of certain compounds of the invention, and a method to obtain these compounds using said precursor compound. Methods of treatment and diagnosis in which the compounds of the invention find use are also provided.

  本发明提供了在治疗和诊断分枝杆菌感染中有用的新化合物。与相关已知化合物相比，本发明的化合物具有增强的生物特性。本发明还提供了一种在合成本发明某些化合物时有用的前体化合物，以及使用该前体化合物获得这些化合物的方法。本发明还提供了利用本发明化合物的治疗和诊断方法。
• DIAGNOSTIC AGENT FOR INFECTIOUS DISEASES
  申请人：Sakurai Kazuhisa

  公开号：US20120219500A1

  公开（公告）日：2012-08-30

  A diagnostic agent for infectious diseases which is capable of distinguishing among different kinds of bacterial species and which allows simple and non-invasive measurement and/or imaging in a short period of time is provided; and a screening method for a therapeutic agent for infectious diseases caused by microorganisms are provided. A diagnostic agent for infectious diseases caused by nitroimidazole susceptible microorganisms, containing an imidazole derivative or a fused imidazole derivative having at least one nitro group on an imidazole ring, or a labeled form thereof as an active ingredient is provided.

  提供了一种针对传染病的诊断试剂，能够区分不同种类的细菌，并允许在短时间内进行简单、非侵入性的测量和/或成像；同时提供了一种筛选治疗由微生物引起的传染病的方法。提供了一种针对对硝基咪唑敏感微生物引起的传染病的诊断试剂，其包含一种咪唑衍生物或至少在咪唑环上具有一个硝基基团的融合咪唑衍生物，或其标记形式作为活性成分。
• Synthesis and Characterization of Lipophilic 1-(18F)Fluoroalkyl-2-nitroimidazoles for Imaging Hypoxia.
  作者：Fumihiko YAMAMOTO、Hidenobu OKA、Shigetoshi ANTOKU、Yu-ichi ICHIYA、Kouji MASUDA、Minoru MAEDA

  DOI：10.1248/bpb.22.590

  日期：——

  was suggested from a comparative study of in vitro radiosensitization in V79 cells that these lipophilic analogs may have reduction potentials close to those of fluoromisonidazole (FMISO) and misonidazole (MISO), known hypoxic cell radiosensitizers. The preparation of 18F-labeled FON (18FON) and FPN (18FPN) was achieved via two-steps through [18F]fluoride ion displacement of tosylate precursors, in

  为了开发脑缺氧的新的成像标记，合成了两种亲脂性硝基咪唑，1-（3-氟丙基）-2-硝基咪唑（FPN）和1-（8-氟辛基）-2-硝基咪唑（FON），并用氟标记-18。测量辛醇/水分配系数作为亲脂性的指标，分别给出FPN的logP = 0.28和FON的logP = 2.72的值，该值被认为是分子在血脑中扩散的最佳范围屏障。通过对V79细胞进行体外放射增敏的比较研究表明，这些亲脂性类似物的还原电位可能与已知的低氧细胞放射增敏剂氟咪唑（FMISO）和米诺唑（MISO）的还原电位接近。18F标记的FON（18FON）和FPN（18FPN）的制备是通过两步完成甲苯磺酸酯前体的[18F]氟离子置换，以合理的放射化学产率进行的。研究了静脉注射后正常大鼠和荷瘤小鼠中18FPN和18FON的组织分布，并与18F标记的FMISO（18FMISO）（一种公认的低氧显像剂）的行为进行了比较。相对于18FMISO，1
• [EN] COMPOUNDS AND METHODS FOR SELECTIVE IMAGING AND/OR ABLATION<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR L'IMAGERIE ET/OU L'ABLATION SÉLECTIVES
  申请人：AUCKLAND UNISERVICES LTD

  公开号：WO2014007650A1

  公开（公告）日：2014-01-09

  The invention relates generally to compounds and methods for imaging and/or selective ablation of nitroreductase-expressing cells and/or biological agents. More particularly, although not exclusively, the invention provides compounds that are selectively metabolised by bacterial nitroreductases and are substantially insensitive to metabolism under oxic or hypoxic conditions by human nitroreductase enzymes.

  本发明涉及一般化合物和方法，用于成像和/或选择性消融硝基还原酶表达细胞和/或生物制剂。更具体地，尽管不是唯一的，本发明提供了一些选择性被细菌硝基还原酶代谢并且在氧化或缺氧条件下对人体硝基还原酶酶不敏感的化合物。
• Compounds And Methods For Selective Imaging And/Or Ablation
  申请人：Auckland Uniservices Limited

  公开号：US20150010474A1

  公开（公告）日：2015-01-08

  The invention relates generally to compounds and methods for imaging and/or selective ablation of nitroreductase-expressing cells and/or biological agents. More particularly, although not exclusively, the invention provides compounds that are selectively metabolised by bacterial nitroreductases and are substantially insensitive to metabolism under oxic or hypoxic conditions by human nitroreductase enzymes.

  本发明涉及化合物和方法，用于成像和/或选择性消融硝基还原酶表达的细胞和/或生物制剂。更具体地说，虽然不仅限于此，本发明提供的化合物被细菌硝基还原酶选择性代谢，且在人类硝基还原酶酶下氧化或缺氧条件下代谢相对不敏感。