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Extended type fluorescent nucleoside analog and preparing method thereof

A technology of nucleoside analogs and fluorescence, which is applied to the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., can solve the problems of cumbersome post-processing, harsh conditions, and low product yields, and achieve excellent fluorescence properties, Apply a wide range of effects

Inactive Publication Date: 2017-05-24
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of nucleoside analogs has the disadvantages of long reaction steps, harsh conditions, cumbersome post-treatment and low yield of products.

Method used

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  • Extended type fluorescent nucleoside analog and preparing method thereof
  • Extended type fluorescent nucleoside analog and preparing method thereof
  • Extended type fluorescent nucleoside analog and preparing method thereof

Examples

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Effect test

example 1

[0024] Example 1: Synthesis of 5-iodo-2,2'-dithiophene

[0025] Add 0.499g (3mmol) of 2,2'-dithiophene, 0.810g (3.6mmol) of N-iodosuccinimide and 30ml of chloroform into the round-bottomed flask respectively, then stir and raise the temperature to 20~50℃ to react for 7 hours . After cooling to room temperature, adding 5 ml of deionized water to precipitate impurities, and then extracting with ethyl acetate (3×5 ml), after rotary evaporation, 0.75 g of white solid was obtained, and the yield was 86%.

example 2

[0026] Example 2: Synthesis of 2,2'-dithiophene acetylide

[0027] Under the protection of nitrogen, add the crude product 5-iodo-2,2'-dithiophene, 25ml N,N-dimethylformamide, 0.46ml (3.6mmol) trimethylsilicon into the reaction tube. Acetylene, 0.08g (0.12mmol) of bistriphenylphosphorus palladium dichloride, 0.11g (0.57mmol) of cuprous iodide, and 1,7ml (12mmol) of triethylamine, the temperature is raised to 50-70°C and reacted for 4 hours. After the temperature dropped to room temperature, 1 g (4.5 mmol) of potassium carbonate was added, and the mixture was stirred at room temperature for 3 hours, and the solution was light brown. After filtration and rotary evaporation, 10 ml of deionized water was added, and the mixture was extracted with ethyl acetate (3×5 ml). After the combined organic phases were rotary evaporated, 0.39 g of light brown solid was obtained, and the yield was 83%.

example 3

[0028] Example 3: Synthesis of fluorescent nucleoside analogues

[0029] Under the protection of nitrogen, add the 2,2'-dithiophene acetylide obtained in the previous step, 0.37g (1mmol) 5-iodouridine, and 0.06g (0.05mmol) bistriphenylphosphonium dichloride into the reaction tube. Palladium, 0.01g (0.07mmol) of cuprous iodide, 0.7ml (5.3mmol) of triethylamine and 20ml of N,N-dimethylformamide, react at 65-70°C for 4 hours. The solid was removed by filtration, the filtrate was concentrated and diluted with 10 ml of dichloromethane, washed with saturated brine three times, and the organic phase was dried over anhydrous sodium sulfate overnight. After filtration and rotary evaporation, the nucleoside derivative 0.60 g (light yellow solid) was obtained by passing through the column with a methanol / dichloromethane mixed solvent, and the yield was 70%.

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Abstract

The invention aims at providing a synthesis method of obtaining a fluorescent nucleoside analog by adopting 2, 2'-bithiophene and 5-iodouridine as raw materials and through a reaction with a palladium catalyst. The method is characterized by comprising the steps of 1, stirring 2, 2'-bithiophene and N-iodosuccinimide for seven hours at the temperature of 20-50 DEG C, and obtaining an intermediate product through treatment; 2, stirring the product in the last step and the catalyst for 4-6 hours at the temperature of 50-70 DEG C, reducing the temperature to the room temperature, adding a certain amount of potash, stirring for 3 hours again, and obtaining 2, 2'-bithiophene acetylide; 3, dissolving the product in the last step, 5-iodouridine, a certain amount of palladium catalyst and cuprous iodide into N, N-dimethylformamide to be subjected to a reaction for 2-5 hours at the temperature of 65-70 DEG C, and obtaining a final product through separation and purification. The fluorescent nucleoside analog is similar to natural nucleoside in structure, has good fluorescence characteristics, can be applied as a fluorescent nucleoside probe, and has a good application prospect in the fields of biochemistry, medicine and the like.

Description

Technical field [0001] The present invention is an extended fluorescent nucleoside analogue and a preparation method thereof. Two thiophenes form a conjugated structure with a pyrimidine ring through an alkyne bond, so that natural nucleosides show good fluorescence characteristics and can be used as fluorescent nucleoside probes. It has good application prospects in the fields of biochemistry and medicine. [0002] technical background [0003] Nucleic acid is an important genetic material of living organisms. It plays a vital role in a series of major life phenomena such as growth, heredity, and mutation. Its research has long been the focus of various research fields such as molecular biology and biochemistry. Nucleoside compounds occupy an important position in anti-tumor, anti-viral and anti-AIDS drugs, and are currently recognized as a class of drugs with anti-viral potential. [0004] At present, the research work of nucleic acid mainly relies on technical means such as fluor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/067C07H1/00C09K11/06
CPCC07H19/067C07H1/00C09K11/06C09K2211/1044C09K2211/1088C09K2211/1092
Inventor 洪建权翟文姬郑昌戈
Owner JIANGNAN UNIV
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