3-(2-硝基-1H-咪唑-1-基)-1,2-丙二醇 | 13551-92-3

• 物质功能分类: 有机原料 - 杂环化合物
• 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: 3-(2-硝基-1H-咪唑-1-基)-1,2-丙二醇
• 中文别名: 3-(2-硝基-1H-咪唑基-1-基)丙烷-1,2-二醇
• 英文名称: O-Desmethyl-misonidazole
• 英文别名: 3-(2-nitro-1H-imidazol-1-yl)propane-1,2-diol；1-(2-nitro-1-imidazolyl)-3-hydroxypropanol；3-(2-nitroimidazol-1-yl)propane-1,2-diol；3-(2-nitro-imidazol-1-yl)-propane-1,2-diol；desmethylmisonidazole；2-Hydroxy-3-(2-nitro-1-imidazolyl)-propanol
• CAS: 13551-92-3
• 化学式: C₆H₉N₃O₄
• mdl: MFCD00866412
• 分子量: 187.155
• InChiKey: NUGLIYXAARVRPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 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：
  104
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  3-(2-硝基-1H-咪唑-1-基)-1,2-丙二醇 在 N-溴酞亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以79%的产率得到3-(4-bromo-2-nitroimidazol-1-yl)propane-1,2-diol
  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
• 作为产物：
  描述：

  1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-nitro-1H-imidazole 在 Dowex 50Wx₄ 作用下， 以 水 为溶剂， 反应 2.0h， 以6.38 g的产率得到3-(2-硝基-1H-咪唑-1-基)-1,2-丙二醇
  参考文献：
  名称：

  A New and Improved Synthesis of the Precursor of the Hypoxia Marker [¹8F]-FMISO

  摘要：

  第 V 组金属化合物与三氧化硫的反应

  DOI：

  10.1055/s-0030-1258269

文献信息

• PRECURSOR COMPOUND CONNECTED TO SOLID SUPPORT FOR MANUFACTURING 18F RADIOPHARMACEUTICAL, METHOD FOR MANUFACTURING SAME, AND APPLICATION THEREOF
  申请人：Chi Dae-Yoon

  公开号：US20140011961A1

  公开（公告）日：2014-01-09

  The present invention relates to a solid precursor in the form of an organic salt, the solid precursor having a solid support, a method for manufacturing same, and an application thereof. The solid precursor of the present invention enables omission of the [ 18 F]fluoride refining process using additional cartridge, and the use of excessive phase-transfer catalyst, and can easily remove remaining substance after reaction through the solid support inside the precursor. The solid precursor of the present invention is very appropriate for an automated synthesis device as an all-in-one system that can carry out overall process of [ 18 F]fluorosis reaction, when used by charging in a cartridge.

  本发明涉及一种有机盐形式的固体前体，该固体前体具有固体支撑物，以及制造该固体前体的方法和其应用。本发明的固体前体使得可以省略使用额外的装置进行[ 18 F]氟化物精制过程，并且可以使用过量的相转移催化剂，并且可以通过前体内部的固体支撑物轻松去除反应后剩余物质。本发明的固体前体非常适用于作为一种全自动合成装置，可以通过在装置中充电使用，执行[ 18 F]氟化反应的整个过程。
• Practical Synthesis of 1‐(2‐Nitro‐1<i>H</i>‐imidazol‐1‐yl)‐3‐(tosyloxy)propan‐2‐yl acetate for the Radiosynthesis of [<scp>¹⁸F</scp>]‐<scp>FMISO</scp>
  作者：Young‐Do Kwon、Eun‐taek Seol、SeokTae Lim、Myung‐Hee Sohn、Hee‐Kwon Kim、Yongju Jung、Seung Jae Lee

  DOI：10.1002/bkcs.10107

  日期：2015.2

  Hypoxia is related with many tumors due to a decreased oxygen condition. Novel synthesis for 1‐(2‐nitro‐1H‐imidazol‐1‐yl)‐3‐(tosyloxy)propan‐2‐yl acetate for the radiosynthesis of the [ ¹⁸F]‐Flouromisonidazole ([ ¹⁸F]‐FMISO), a hypoxia imaging marker used in positron emission tomography, from the readily available starting material is described. In this approach, one‐pot two‐step syntheses were used for the preparation of the [ ¹⁸F]‐FMISO precursors that contain acetyl group. The mild reaction conditions and easy treatments are attractive features in this synthesis. This new synthetic route provides alternative choices for the preparation of hypoxia imaging marker.

  缺氧与许多肿瘤有关，因为氧气含量降低。1-(2-硝基-1H-咪唑-1-基)-3-(对甲苯磺酰氧基)丙-2-基乙酸酯的新合成方法，用于[18F]-氟苯并咪唑（[[18F]-FlouromISOnidazole）的放射合成。 18F]-FlouromISOnidazole ([ 18F]-FMISO），这是一种用于正电子发射断层扫描的缺氧成像标记物。该方法采用一锅两步合成法制备了[18F]-FMISO。 18F]-FMISO 前体。这种合成方法的特点是反应条件温和、处理简单。这种新的合成路线为制备缺氧成像标记物提供了另一种选择。
• 2‐Nitroimidazole Based PET Tracers: Development of a General Synthetic Approach and Fluorination Methodology
  作者：Kévin Renault、Romain Horion、Xavier Maes、Maha Rzeigui、Yoann Joyard、Nicolas Maindron、Vincent Tadino、Stéphane Vincent

  DOI：10.1002/ejoc.202300307

  日期：2023.7.8

  In this work, a general approach for the synthesis of fluorinated nitroimidazoles is described.

  在这项工作中，描述了合成氟化硝基咪唑的一般方法。
• Facile and Efficient Synthesis of [¹⁸F]Fluoromisonidazole Using Novel 2-Nitroimidazole Derivatives
  作者：Young-Do Kwon、Yongju Jung、Seok Tae Lim、Myung-Hee Sohn、Hee-Kwon Kim

  DOI：10.5935/0103-5053.20160010

  日期：——

  [F-18]Fluoromisonidazole ([F-18]FMISO) is a hypoxia imaging marker utilized in positron emission tomography. Novel FMISO precursors were prepared from a commercially available material, and several reaction factors that affect synthesis of [F-18]FMISO were examined to achieve a higher fluorination yield. [F-18]FMISO was obtained from radiosynthesis, followed by the hydrolysis of protecting groups with HCl. New 2-nitroimidazole precursor showed a higher [F-18]fluorination and a higher synthetic yield. This result provided alternative guidelines for the preparation of hypoxia imaging marker.
• Chan, Peter K. L.; James, Brian R.; Frost, David C., Canadian Journal of Chemistry, 1989, vol. 67, p. 508 - 516
  作者：Chan, Peter K. L.、James, Brian R.、Frost, David C.、Chan, Paul K. H.、Hu, Hong-Liang、Skov, Kirsten A.

  DOI：——

  日期：——