1-azido-3-([(18)F]fluoromethyl)benzene | 1255916-25-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-azido-3-([(18)F]fluoromethyl)benzene
• 英文别名: 1-azido-3-((18F)fluoranylmethyl)benzene
• CAS: 1255916-25-6
• 化学式: C₇H₆FN₃
• 分子量: 150.145
• InChiKey: SEVXYDSYOAHLMG-COJKEBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-azidobenzyl 4-methylbenzenesulfonate 在 四丁基铵碳酸氢酯 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以96%的产率得到1-azido-3-([(18)F]fluoromethyl)benzene
  参考文献：
  名称：

  Stoichiometry-focused 18F-labeling of alkyne-substituted oligodeoxynucleotides using azido([18F]fluoromethyl)benzenes by Cu-catalyzed Huisgen reaction

  摘要：

  A novel method for F-18-radiolabeling of oligodeoxynucleotides (ODNs) by a Cu-catalyzed Huisgen reaction has been developed by using the lowest possible amount of the precursor biomolecule for the realization of stoichiometry-oriented PET (positron emission tomography) chemistry. Under the optimized cyclization conditions of p- or m-azido([F-18]fluoromethyl)benzene and alkyne-substituted ODN (20 nmol) at 40 degrees C for 15 min in the presence of CuSO4, TBTA [tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl) amine], and sodium ascorbate (2:1:2), the synthesis of F-18-labeled ODNs with sufficiently high radioactivities of 2.1-2.5 GBq and specific radioactivities of 1800-2400 GBq/mu mol have been accomplished for use in animal and human PET studies. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.033

文献信息

• 18F-LABELED AZIDE COMPOUND, REAGENT FOR 18F-LABELING AND METHOD FOR 18F-LABELING OF ALKYNE COMPOUND USING SAME
  申请人：Watanabe Yasuyoshi

  公开号：US20120101266A1

  公开（公告）日：2012-04-26

  [OBJECT] The present invention provides an 18 F-labeled azide compound usable in the Huisgen reaction which enables 18 F-labeling although only a small quantity of alkyne compound is available as a counterpart substrate, more specifically the 18 F-labeled azide compound enabling the PET to be applied to peptides or oligonucleotides and enabling the 18 F-labeling of any sites of oligonucleotide other than the 5′ end or 3′ end thereof, a reagent for 18 F-labeling, and a method for 18 F -labeling of an alkyne compound using the same. [SOLVING MEANS] An 18 F-labeled azide compound according to the present invention is expressed by the following structural formula 1. [SELECTED DRAWING] None

  本发明提供了一种18F标记的叠氮化合物，可用于Huisgen反应，即使只有少量炔化合物作为对应底物，也能进行18F标记。具体而言，该18F标记的叠氮化合物使PET技术能够应用于肽或寡核苷酸，并且能够在寡核苷酸的5'端或3'端之外的任何位点进行18F标记，还提供了用于18F标记的试剂，以及使用该试剂对炔化合物进行18F标记的方法。根据本发明，所述的18F标记的叠氮化合物可由以下结构式1表示。
• US8680260B2
  申请人：——

  公开号：US8680260B2

  公开（公告）日：2014-03-25
• Stoichiometry-focused 18F-labeling of alkyne-substituted oligodeoxynucleotides using azido([18F]fluoromethyl)benzenes by Cu-catalyzed Huisgen reaction
  作者：Takeshi Kuboyama、Motoi Nakahara、Masafumi Yoshino、Yilong Cui、Takeo Sako、Yasuhiro Wada、Takeshi Imanishi、Satoshi Obika、Yasuyoshi Watanabe、Masaaki Suzuki、Hisashi Doi

  DOI：10.1016/j.bmc.2010.11.033

  日期：2011.1

  A novel method for F-18-radiolabeling of oligodeoxynucleotides (ODNs) by a Cu-catalyzed Huisgen reaction has been developed by using the lowest possible amount of the precursor biomolecule for the realization of stoichiometry-oriented PET (positron emission tomography) chemistry. Under the optimized cyclization conditions of p- or m-azido([F-18]fluoromethyl)benzene and alkyne-substituted ODN (20 nmol) at 40 degrees C for 15 min in the presence of CuSO4, TBTA [tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl) amine], and sodium ascorbate (2:1:2), the synthesis of F-18-labeled ODNs with sufficiently high radioactivities of 2.1-2.5 GBq and specific radioactivities of 1800-2400 GBq/mu mol have been accomplished for use in animal and human PET studies. (C) 2010 Elsevier Ltd. All rights reserved.