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Allopurinol derivative and preparation method and application thereof

A technology for medicines and compounds, applied in the field of allopurinol derivatives and their preparation, achieves the effects of inhibiting activity, inhibiting tumor growth, and simple preparation method

Active Publication Date: 2012-10-24
SICHUAN GUOKANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, there are no relevant reports about using allopurinol as a lead compound for anti-tumor after structural modification and transformation

Method used

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  • Allopurinol derivative and preparation method and application thereof
  • Allopurinol derivative and preparation method and application thereof
  • Allopurinol derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of 1-N-ethyl-4-hydrazino-1H-pyrazol[3,4-d]pyrimidine (Compound 4 for short)

[0034]

[0035] (1) Synthesis of 4-chloro-1-ethyl-1H-pyrazol[3,4-d]pyrimidine (Compound 3 for short)

[0036] Dissolve 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (0.1g, 0.65mmol) in 5mL of dry DMF, stir the reaction solution at room temperature for 10min, and slowly add a good amount with a dropping funnel triethylamine (0.20 g, 1.95 mmol), and the mixture was stirred at room temperature for 30 min. Bromoethane (0.084 g, 0.78 mmol) dissolved in 3 mL of dry DMF was slowly added dropwise to the mixture, stirring was continued for 1 h and then a catalytic amount of KI was added. The reaction solution was detected by TLC until complete reaction was detected, the mixture was poured into 15 mL of water, and the pH was adjusted to acidic with dilute hydrochloric acid, then extracted with ethyl acetate (4×20 mL), the organic layer was washed with saturated sodium chloride, anhydrous...

Embodiment 2

[0041] Example 2 (N-((4-chloroacetamido) phenyl)-4-amino-1H-pyrazol[3,4-d]pyrimidine-N-1-)-2-ethyl acetate (compound for short 8e) Preparation

[0042]

[0043] (1) Synthesis of ethyl (4-chloro-1H-pyrazol[3,4-d]pyrimidine-N-1-)-2-acetate (Compound 6 for short)

[0044] Slowly add TEA (1.78g, 17.62mmol) into 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (0.81g, 5.26mmol) dissolved in 20mL dry DMF, stir at room temperature for 30min, Ethyl bromoacetate (1.06 g, 6.39 mmol) dissolved in 5 mL of dry DMF was slowly added dropwise to the mixture and stirring was continued for 2 h. The reaction solution was detected by TLC and poured into 30mL of water after the reaction was complete. After adjusting the pH value to acidic with dilute hydrochloric acid, it was extracted with ethyl acetate (3×25mL). The organic layer was washed with saturated sodium chloride and concentrated to obtain flocs . The crude product was subjected to silica gel column chromatography and eluted with petroleum et...

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PUM

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Abstract

The invention provides an allopurinol derivative as shown in Formula I, and a preparation method and application thereof. Tumor growth can be effectively suppressed by the allopurinol derivative provided by the invention, the activity of the allopurinol derivative is equivalent to that of 17-AGG (17-allylamide-17-demethoxygeldanamycin) to which phase III clinical trial is performed, and the allopurinol derivative has a good antitumor effect. The activity of xanthine oxidase can be effectively suppressed by the allopurinol derivative, and the allopurinol derivative can be used for treating gout and provides a new drug choice for clinically treating cancer and gout. Additionally, the preparation method of the compound provided by the invention has the advantages of simplicity, lower cost, high yield and good industrial application prospect.

Description

technical field [0001] The present invention relates to allopurinol derivatives and their preparation methods and applications. Background technique [0002] Tumor is one of the most common and serious diseases that threaten human life in the world today. Chemotherapy, radiotherapy, and surgery are currently the main means of treating tumors. However, the number of drugs currently used for tumor treatment is limited, and their prices are high, which brings a greater economic burden to cancer patients. Therefore, it is particularly necessary to develop more effective anti-tumor drugs. [0003] Allopurinol, chemical name: 4-hydroxy-1H-pyrazolo[3,4-d]pyrimidine, its structural formula is as follows: [0004] [0005] It is an isomer of natural hypoxanthine, which can inhibit the activity of xanthine oxidase, prevent the oxidation of xanthine and hypoxanthine to produce uric acid, thereby reducing the concentration of serum uric acid, and is mainly used for the treatment o...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P19/06A61P35/00
CPCC07D487/04A61K31/519A61P19/06A61P35/00
Inventor 李财虎石万棋赵洪祥李剑忠李颖董林尹述凡
Owner SICHUAN GUOKANG PHARMA
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