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18F labelled precursor compound and preparation method and application thereof

A precursor compound and labeling technology, applied in the preparation of organic compounds, organic chemistry methods, chemical instruments and methods, etc., can solve the problems of unstable metabolism in vivo, long reaction time, low reaction yield, etc., and achieve fast and efficient labeling , the effect of short reaction time and high radioactive yield

Inactive Publication Date: 2012-11-14
ZHEJIANG UNIV
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Problems solved by technology

[0003] Although 18F is the most widely used positron nuclide, because of its chemical properties, 18F cannot be directly labeled on drugs or diagnostic reagents. It must be labeled on the corresponding precursor first, and then the target compound is labeled. At present, there are many corresponding 18F-labeled precursors have been synthesized, but they all have their own shortcomings, such as: low reaction yield, long reaction time, unstable metabolism in vivo, etc. 【5~8】

Method used

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  • 18F labelled precursor compound and preparation method and application thereof
  • 18F labelled precursor compound and preparation method and application thereof
  • 18F labelled precursor compound and preparation method and application thereof

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Embodiment 1

[0043] The synthesis of embodiment 1,3-nitro-4-fluorobenzoyl propargyl amine comprises the following steps successively:

[0044] 1), the synthesis of 3,4-dinitrobenzoyl propargyl amine:

[0045]

[0046] Add 212mg (1mmol) of 3,4-dinitrobenzoic acid, 55mg (1.1mmol) of propynylamine, 288mg (1.5mmol) of EDC·HCl, and 67.5mg (0.5mmol) of HOBt into a 50mL round-bottomed flask in turn, and then add 20mL DMF, react at 40℃~50℃ for 10h.

[0047] After the reaction is complete, add 30mL of ethyl acetate, then wash with water (20mL*3), and then undergo rotary evaporation (evaporate at 40°C at a speed of 150 rpm); the residue after evaporation is separated by silica gel column, specifically For: use dichloromethane:methanol=9:1 (volume ratio) mobile phase to separate through a silica gel column (200-300 mesh) to obtain 130mg of the product. The product is 3,4-dinitrobenzoyl propargyl amide in the form of light yellow solid; the 3,4-dinitrobenzoyl propargyl amide is the precursor comp...

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Abstract

The invention discloses a 18F labelled precursor compound of which structural formula is shown as below, wherein R1 is hydrogen, methyl, ethyl, propyl, isopropyl and butyl, n is an integer ranging from 1 to 5; and F is 19F or 18F. The invention also discloses a preparation method of the compound. The method comprises the following steps in turn: 1) the synthesis of the labelled precursor compound: dissolving 3,4-dinitrobenzoic acid, amino alkyne, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole in dimethylformamide, stirring to react; postprocessing the product of the reaction to obtain a precursor compound; and 2) the labelling of the precursor compound. The 18F labelled precursor compound can be used in the clickchemistry method to label amino acidsand polypeptide compounds and can also be used as molecular imaging probe in the positron emission tomography (PET) mapping.

Description

technical field [0001] The invention belongs to the technical field of 18F labeling, and the specific invention relates to a novel 18F labeling precursor compound and its preparation method and application. Background technique [0002] Positron emission tomography PET (Positron emission tomography PET) imaging technology is currently the most important technology in the field of molecular imaging. It has very high sensitivity and resolution, and can provide dynamic and real-time information on the transport and metabolism changes of drugs or metabolites in the body. [1, 2]. Among many positron radionuclides, 18F(t 1 / 2 =109.8min) has become the most widely used positron nuclide due to its excellent properties [3,4]. At present, 18F-FDG has been widely used in clinical diagnosis and evaluation after tumor surgery. [0003] Although 18F is the most widely used positron nuclide, because of its chemical properties, 18F cannot be directly labeled on drugs or diagnostic reagent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/65C07C231/12C07B59/00C07D249/04A61K51/04
Inventor 李业森徐宇虹张岚刘雅琴施玲丽
Owner ZHEJIANG UNIV
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