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18/19F-ester nitroimidazole compound, preparation method thereof and application as hypoxic tissue developing agent

A technology of nitroimidazole and compound, applied in the field of radiopharmaceutical chemistry, can solve the problems of poor pharmacokinetic properties, poor metabolic stability and the like

Inactive Publication Date: 2014-09-03
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many candidate imaging agents were eliminated due to poor metabolic stability in vivo, poor pharmacokinetic properties, etc.

Method used

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  • 18/19F-ester nitroimidazole compound, preparation method thereof and application as hypoxic tissue developing agent
  • 18/19F-ester nitroimidazole compound, preparation method thereof and application as hypoxic tissue developing agent
  • 18/19F-ester nitroimidazole compound, preparation method thereof and application as hypoxic tissue developing agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Br-MNEFT, i.e. (2-(2-methyl-5-nitro-1-imidazolyl))ethyl 2-bromoacetate

[0057] Preparation of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-bromoacetate (compound 7 for short):

[0058]

[0059] 2-Methyl-5-nitroimidazole-1-ethanol (1.06mmol, 182mg) was dissolved in 10mL of dichloromethane, and triethylamine (0.6mL) and bromoacetyl bromide (2.87mmol, 579mg, 0.25mL), the reaction was stirred overnight. Then, the reaction mixture solution was diluted with 30 mL of dichloromethane, washed with water (10 mL×2) and saturated brine (10 mL). The resulting organic phase was dried over anhydrous sodium sulfate. After filtration, dichloromethane was distilled off under reduced pressure, and the obtained oil was separated by column chromatography using a silica gel column with ethyl acetate / n-hexane = 1 / 1 (v / v) as the eluent, and the product components were collected and distilled under reduced pressure. The solvent was removed to obtain 146 mg of compound 7 as a pale yellow ...

Embodiment 2

[0063] F-MNEFT, namely (2-(2-methyl-5-nitro-1-imidazolyl))ethyl 2-fluoroacetate

[0064] Preparation of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-fluoroacetate (compound 8 for short):

[0065]

[0066] 2-Methyl-5-nitroimidazole-1-ethanol (1.04mmol, 178mg) was dissolved in 10mL of dichloromethane, triethylamine (1.1mL) and fluoroacetyl chloride (2.23mmol, 193 mg, 0.17 mL). After 3 h the mixture was brought to room temperature and the reaction was stirred overnight. Then, the reaction mixture solution was diluted with 20 mL of dichloromethane, washed with water (10 mL×2) and saturated brine (10 mL). The resulting organic phase was dried over anhydrous sodium sulfate. After filtration, dichloromethane was distilled off under reduced pressure, and the obtained oil was separated by column chromatography using a silica gel column with ethyl acetate / n-hexane = 1 / 1 (v / v) as the eluent, and the product components were collected and distilled under reduced pressure. The solven...

Embodiment 3

[0070] Br-NPFT, namely (2-(2-nitro-1-imidazolyl))ethyl 2-bromopropionate

[0071] Preparation of 2-(2-nitro-1H-imidazol-1-yl)ethyl 2-bromopropanoate (compound 9 for short):

[0072]

[0073] 2-Nitroimidazole-1-ethanol (1.03mmol, 162mg) was dissolved in 6mL of dichloromethane, triethylamine (0.4mL) was added dropwise in an ice-water bath, and bromine diluted with 2mL of dichloromethane was added dropwise. Propionyl bromide (0.2 mL), the reaction was stirred overnight. Then, the reaction mixture solution was diluted with 10 mL of dichloromethane, washed with water (5 mL×2) and saturated brine (5 mL). The obtained organic phase was dried over anhydrous sodium sulfate. After filtration, dichloromethane was distilled off under reduced pressure, and the resulting oil was separated by column chromatography using a silica gel column with ethyl acetate / n-hexane=2 / 3 (v / v) as the eluent, and the product components were collected and distilled under reduced pressure The solvent was ...

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Abstract

The invention relates to an 18 / 19F-ester nitroimidazole compound, preparation method thereof and application as a hypoxic tissue developing agent. The invention provides F-ester nitroimidazole compounds as shown in a general formula, wherein an 18F-ester nitroimidazole compound is a radioactive compound. According to an S180 tumor-bearing mice experiment, the 18F-ester nitroimidazole compound has the characteristics of good tumor targeted intake and low liver background level, and is a potential positron emission tomography (PET) hypoxic tissue developing agent.

Description

technical field [0001] The invention belongs to the field of radiopharmaceutical chemistry, and relates to a novel hypoxic tissue imaging agent, more specifically, to a class of F( 18 F)-ester nitroimidazole compounds and precursor compounds thereof, methods for preparing these compounds, and 18 Use of F-ester nitroimidazole compounds as hypoxic tissue imaging agents. Background technique [0002] Hypoxia is a major feature of many major diseases, and it is widely found in major diseases such as tumors, brain and myocardium. The use of hypoxic tissue imaging agents for nuclear medicine PET imaging is currently the most potential and most promising method for clinical diagnosis of oxygen levels. 18 Due to its excellent nuclide properties, F-labeled PET imaging agents play an extremely important role in the development and application of PET imaging agents, and have become a hot spot in the current radiopharmaceutical research. [0003] An ideal hypoxic tissue imaging agent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/91C07D233/60A61K51/04
Inventor 朱霖乔晋萍杜晶磊
Owner BEIJING NORMAL UNIVERSITY
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