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A kind of tritium-labeled metronidazole and preparation method thereof

A metronidazole and labeling technology, applied in organic chemistry methods, organic chemistry and other directions, can solve problems such as excessive residues, lack of metronidazole metabolism, research on residues and elimination, affecting food safety and monitoring human health, etc., to achieve high safety. , good antibacterial effect

Inactive Publication Date: 2019-05-17
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, relevant toxicological studies have shown that it is potentially carcinogenic and mutagenic. In order to ensure food safety, many countries have banned its use on food animals for the purpose of anti-stress and growth promotion. It is only allowed to be used as a therapeutic drug, but Not to be detected in food of animal origin
However, there are still illegal use and abuse of metronidazole in actual production, resulting in excessive residues in animals, and residues in food animal tissues seriously affect food safety monitoring and human health
[0003] There is a lack of research on the metabolism, residue and elimination of metronidazole in animals in the content of the food safety toxicology evaluation test

Method used

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  • A kind of tritium-labeled metronidazole and preparation method thereof
  • A kind of tritium-labeled metronidazole and preparation method thereof
  • A kind of tritium-labeled metronidazole and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) Add 6.35 g of 2-methyl-5-nitroimidazole and 50 ml of N,N-dimethylformamide in sequence in a reaction vessel with a stirring device and equipped with a thermometer, stir and dissolve the raw materials at 40°C, and divide Add 11.25 g of N-iodosuccinimide in batches, react at 80°C for 5 hours, cool the reaction solution to 20°C, add an equal volume of ice water to the reaction solution, filter to obtain a yellow solid, and use 10% Sodium thiosulfate aqueous solution and refrigerated distilled water were washed, the obtained solid was filtered, recrystallized with ethanol, and vacuum-dried to obtain 4-iodo-2-methyl-5-nitroimidazole in the form of light yellow crystals with a yield of 65%.

[0034] (2) Add 6.35g of 2-methyl-5-nitroimidazole and 60ml of N,N-dimethylformamide successively into a reaction vessel equipped with a thermometer equipped with a stirring device, stir and dissolve the raw materials at 40°C, and divide Add 16.87 g of N-iodosuccinimide in batches, re...

Embodiment 2

[0037] (1) In the 5mL micro-reaction bottle, add magneton successively, then add 50 mg of 4-bromo-2-methyl-5-nitroimidazole prepared in Example 1, add 3 mL of methanol to completely dissolve it, and then add 5 mg of 10% Concentration of palladium carbon (Pd / C) as catalyst. The reaction bottle was placed on a hydrogenation device and fed with high-purity hydrogen gas, replaced three times, the reaction pressure was adjusted to 100mmHg, and the reaction was kept at 25°C for 30 minutes with stirring. The reaction was stopped, Pd / C was removed by centrifugation, and the remaining liquid was evaporated to dryness under reduced pressure to obtain 2-methyl-5-nitroimidazole, which was analyzed by HPLC with a yield of 47%.

[0038] (2) Add magneton successively in 5mL micro reaction vial, then add 4-bromo-2-methyl-5-nitroimidazole 50mg prepared in Example 1, add 3mL methanol to make it dissolve completely, then add 2.5mg 10 % concentration of Pd / C. The reaction bottle was placed on a...

Embodiment 3

[0044] (1) Add 100 mg of formic acid and 20 mg of concentrated sulfuric acid to a reaction vessel equipped with a thermometer, a stirrer and an air duct respectively to prepare a mixed acid solution, add 25 mg of 2-methyl-5-nitroimidazole to the mixed acid solution, and take another A two-necked reaction flask, add 5ml of ethylene oxide to connect the reaction system, slowly introduce ethylene oxide into the reaction vessel, react at 80°C for 12 hours, add an appropriate amount of 1M sodium hydroxide solution to the reaction solution to adjust the pH To 8, add 5ml of ethyl acetate solvent extraction three times, combine the organic phases, dry with anhydrous sodium sulfate and filter, distill the filtrate to remove the solvent under reduced pressure to obtain 29.5 mg of metronidazole with a yield of 88%.

[0045] (2) Add 75 mg of formic acid and 15 mg of concentrated sulfuric acid to a reaction vessel equipped with a thermometer, a stirrer and an air duct respectively to prepar...

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Abstract

The invention belongs to the field of radioactive isotope labeling preparation, and particularly relates to tritiated metronidazole and a preparation method thereof. The preparation method includes: using 2-methyl-5-nitroimidazole as a raw material to react with N-iodosuccinimide to obtain 4-iodine-2-methyl-5nitroimidazole; under catalysis of palladium carbon, enabling 4-iodine-2-methyl-5nitroimidazole and tritium gas to be in tritium-halogen exchange to generate 4-3H-2-methyl-5-nitroimidazole; enabling 4-3H-2-methyl-5-nitroimidazole to react with ethylene oxide to obtain 4-3H-metronidazole. A synthetic product is purified through a prepared liquid phase to obtain4-3H-metronidazole with high specific activity (22.08Ci / g), high radiochemical purity (greater than or equal to 98%) and high chemical purity (greater than or equal to 98%). The tritiated metronidazole can be used as a radioactive tracer in studying absorption, distribution, metabolism and residue elimination of metronidazole in animal bodies.

Description

technical field [0001] The invention belongs to the field of synthesis of radioactive chemical tracers, and in particular relates to a tritium-labeled metronidazole and a preparation method thereof. The invention uses the radioactive isotope tritium to mark the C4 position of metronidazole so that the tracer can be studied and applied in the law of absorption, distribution, metabolism and residue elimination in animals by using the radioactive isotope tracer method. Background technique [0002] Metronidazole (metronidazole, metronidazole) is a nitridazole drug, mainly used for the treatment of diseases caused by obligate anaerobic bacteria, protozoa and spirochete infection, such as poultry blackhead and amoeba infection. Dysentery caused by Spirulina suis infection. It has the advantages of good antibacterial effect, high safety, and economic benefits, and has been widely used in veterinary clinics and animal husbandry. However, relevant toxicological studies have shown ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/94
CPCC07B2200/05C07D233/94
Inventor 袁宗辉潘源虎黄玲利周波谢书宇陶燕飞陈冬梅刘振利易继亮
Owner HUAZHONG AGRI UNIV
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