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1-N-benzyl allopurinol derivative as well as preparation method and application thereof

A technology of -4-N-2, benzyl, applied in the field of allopurinol derivatives and its preparation, achieving the effects of simple preparation method, inhibition of xanthine oxidase activity, and high yield

Inactive Publication Date: 2013-07-31
SICHUAN UNIV
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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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  • 1-N-benzyl allopurinol derivative as well as preparation method and application thereof
  • 1-N-benzyl allopurinol derivative as well as preparation method and application thereof
  • 1-N-benzyl allopurinol derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0038] Example 14 Synthesis of chloro-1-benzyl-1H-pyrazol[3,4-d]pyrimidine (compound 10 for short)

[0039] Compound 2 (0.1g, 0.65mmol) was dissolved in 5mL of dry DMF, the reaction solution was stirred at room temperature for 10min, and a good amount of triethylamine (0.22g, 0.65mmol) was slowly added dropwise with a dropping funnel, and stirring was continued at room temperature 30min. Benzyl bromide (0.11 g, 0.78 mmol) dissolved in 5 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 mixed solution 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 magnesium sulfate Dry and concentrate. The crude product was subjected to silica gel column chromatogra...

Embodiment 2

[0041] Example 2 Synthesis of N'-(1'-benzyl-1H-pyrazol[3,4-d]pyrimidin-4'-yl-)-1,2-ethylenediamine (compound 11 for short)

[0042] Compound 10 (0.10 g, 0.41 mmol) was dissolved in 10 mL of acetonitrile, and then ethylenediamine (0.025 g, 0.42 mmol) was slowly added to the mixture, stirred at room temperature, and detected by TLC until complete reaction. The reaction solution was concentrated to obtain a yellow oily liquid, and the crude product was subjected to silica gel column chromatography, first passed through the column with dichloromethane:methanol (2:8 drops), and then eluted with methanol to obtain a yellow oily liquid 11.

[0043] 11: yellow oily liquid 1 H NMR (400MHz, DMSO-d 6 )δ:8.61(br,1H,NH),8.25(s,1H,CH),8.03(s,1H,CH),7.19~7.32(m,5H,ArH),5.50(s,2H,CH 2 ),3.59(dd,2H,CH 2 ), 3.13 (dd, J=6.10Hz, J=12.10Hz, 2H, CH2 ),2.88(t,J=6.10Hz,2H,NH 2 ); 13 C NMR (100MHz, DMSO-d 6 )156.47,155.83,152.67,137.33,132.37,128.45,127.40,100.52,49.71,41.26,40.63;IR(KBr,v,cm -...

Embodiment 3

[0044] The synthesis of embodiment 3 compound 12a~12c

[0045] Compound 11 (0.32g, 1.19mmol) and TEA (0.18g, 1.78mmol) were successively added to 10mL of dry DMF under ice-free conditions, stirred for a period of time, and then the benzenesulfonyl chloride dissolved in 2mL of dry DMF (0.25g, 1.79mmol) was slowly added dropwise to the mixture, and stirring was continued under ice bath conditions. The reaction solution was detected by TLC and poured into 15 mL of water, and extracted with ethyl acetate (3×15 mL). The organic layer was washed with saturated sodium chloride and concentrated to obtain a solid. The crude product was subjected to silica gel column chromatography, eluting with petroleum ether:ethyl acetate:methanol (2:2:6 drops), to give 12a as a pale yellow solid.

[0046] Compound 11 (1.19mmol) and TEA (0.18g, 1.78mmol) were successively added to 10mL dry DMF under ice-free conditions, stirred for a period of time, and p-nitrobenzenesulfonyl chloride dissolved in 2...

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Abstract

The invention provides an allopurinol derivative shown in a formula I, as well as a preparation method and an application thereof. The allopurinol derivative can effectively inhibit tumor growth, and has a good antitumor effect; the allopurinol derivative can also effectively inhibit xanthine oxidase activity, can be used for gout treatment, and provides a new pharmaceutical option for clinicallytreating cancer and gout; and moreover, the preparation method of the compound is simple, is lower in cost, and has high yield and a 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P35/00A61P19/06
Inventor 尹述凡宋长伟王裕军李霞袁明兴李颖董林
Owner SICHUAN UNIV
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