Adenine kind derivative and its synthesis method

A technology for adenine and derivatives, applied in the field of adenine derivatives and their preparation, can solve problems such as hazards, difficult sources of raw materials, low biological activity, etc., to improve cytokinin activity, facilitate industrial implementation, and improve anti-inflammatory activity Effect

Active Publication Date: 2008-10-22
SHANGHAI HETENG FINE CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the above disclosed N 6 - position substitution, N 9 - position substitution and N 9 , N 6 The derivatives of double-substituted adenine at the -position have a significant defect, such as low biological activity, difficult source of raw materials, complicated preparation process, and cannot meet the needs of development in related fields. Most of the prior art uses 6-chloropurine and benzylamine As a raw material, the synthesis route is cumbersome, and the toxicity is relatively high, which will bring great harm to the synthesizer itself. However, the present invention uses benzyl bromide with boronic acid groups as a raw material, and uses DImroth rearrangement reaction, which is simple to operate and has low toxicity. It will not cause harm to the body. At present, various inflammatory diseases seriously affect people's health. Therefore, people expect more new adenine derivatives to meet the needs of the development of the medical field

Method used

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  • Adenine kind derivative and its synthesis method
  • Adenine kind derivative and its synthesis method
  • Adenine kind derivative and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] N 9 Synthesis of -(2-boronic acid) benzyl adenine:

[0037]

[0038] Add 270mg (2mmol) of adenine and 300mg (2.15mmol) of anhydrous potassium carbonate to 5ml of freshly steamed DMF to form a suspension, and heat the suspension to 120°C in an oil bath with stirring. Within 60 minutes, 5ml Dissolve 515.5 mg (2.4 mmol) of 2-bromomethylphenylboronic acid in DMF solution, dropwise added to the mixture, and reflux for 14 hours. As the reaction progresses, the color of the suspension gradually becomes darker, and finally it is earthy brown. Filtrate while hot, wash with hot anhydrous DMF 10ml fractions, combine the filtrates, evaporate the DMF under reduced pressure at 45°C, dissolve the concentrate with a small amount of methanol, and separate the product by thin-layer chromatography with a yield of 35.0% (developing agent is dichloro methane:methanol=8:1, volume ratio). The physical property data are shown in Table 1, IR, H 1 See Table 2 for NMR and MS data.

Embodiment 2

[0040] N 9 Synthesis of -(3-boronic acid) benzyl adenine:

[0041]

[0042] Add 270mg (2mmol) of adenine and 300mg (2.15mmol) of anhydrous potassium carbonate to 5ml of freshly steamed DMF to form a suspension, and heat the suspension to 120°C in an oil bath with stirring. Within 60 minutes, 5ml Dissolve 515.5 mg (2.4 mmol) of 3-bromomethylphenylboronic acid in DMF solution, dropwise added to the mixture, and reflux for 14 hours. As the reaction progressed, the color of the suspension gradually became darker, and finally it was earthy brown. Filtrate while hot, wash with hot anhydrous DMF 10ml fractions, combine the filtrates, distill off the DMF under reduced pressure at 45°C, dissolve the concentrate with a small amount of methanol, and separate the product by thin-layer chromatography with a yield of 42.5% (developing agent is dichloro methane:methanol=8:1, volume ratio).

[0043] The physical property data are shown in Table 1, IR, H 1 See Table 2 for NMR and MS data...

Embodiment 3

[0045] N 9 Synthesis of -(4-boronic acid)benzyl adenine

[0046]

[0047] Add 270mg (2mmol) of adenine and 300mg (2.15mmol) of anhydrous potassium carbonate to 5ml of freshly distilled DMF to form a suspension, and heat the suspension to 120°C with stirring. Within 60 minutes, dissolve 5ml of 515.5mg (2.4mmol) DMF solution of 4-bromomethylphenylboronic acid was added dropwise to the mixture, and refluxed for 14 hours. As the reaction progressed, the color of the suspension gradually became darker, and finally it was earthy brown. A large number of precipitates appeared, filtered while hot, washed with hot anhydrous DMF 10ml fractions, finally the precipitate was washed with water to obtain a white substance, dried in a vacuum oven for 1 hour, and recrystallized with methanol to obtain a white granular substance, the yield was : 46.1%.

[0048] The physical property data are shown in Table 1, IR, H 1 See Table 2 for NMR and MS data.

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Abstract

An adenine derivative series is prepared from bromobenze with borate radical through Dimroth rearranging reaction. Its advantage is high activity to suppress proinflammatory factor (tumor necrosis factor alpha) and splitting cell.

Description

technical field [0001] The invention relates to an adenine derivative and a preparation method thereof. Background technique [0002] Adenine is one of the well-known organic compounds essential to life. It is a ring system formed by merging pyrimidine and imidazole rings, and its chemical structure is as follows: [0003] [0004] Adenine is one of the important components of ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) structures. Their properties and reactivity have an important influence on the properties and physiological functions of nucleic acids. Adenine is also the main component of the structure of adenosine triphosphate (ATP), which plays a vital role in biological organisms. Therefore, the research on adenine and its derivatives and activities is highly valued by scientists. Among them, the most studied ones are N 6 - position substitution, N 9 - position substitution and N 9 , N 6 -Derivatives of disubstituted adenine. [0005] However, the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D473/34A61P29/00
Inventor 李改霞田久旺施晓旦
Owner SHANGHAI HETENG FINE CHEM
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