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1-N-ethyl-4-N-2'-substituted acylhydrazine-1H-pyrazol [3, 4-d] miazines derivative as well as preparation method and application thereof

A 4-N-2, 4-d technology, applied in drug combination, bone disease, antineoplastic drugs, etc.

Inactive Publication Date: 2013-06-05
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-ethyl-4-N-2'-substituted acylhydrazine-1H-pyrazol [3, 4-d] miazines derivative as well as preparation method and application thereof
  • 1-N-ethyl-4-N-2'-substituted acylhydrazine-1H-pyrazol [3, 4-d] miazines derivative as well as preparation method and application thereof
  • 1-N-ethyl-4-N-2'-substituted acylhydrazine-1H-pyrazol [3, 4-d] miazines derivative as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 14

[0102] The preparation method of embodiment 14-chloro-1-ethyl-1H-pyrazol[3,4-d]pyrimidine (compound 3 for short)

[0103]

[0104] Dissolve 4-chloro-1H-pyrazolo[3,4-d]pyrimidine (0.1g, 0.65mmol) in 5mL dry DMF at normal pressure, stir the reaction solution at room temperature for 10min, and slowly A good amount of triethylamine (0.20 g, 1.95 mmol) was added dropwise, 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 magnesium sulfate Dry and concentrate to an oil. The crude product was ...

Embodiment 2

[0106] Example 2 Synthesis of 1-ethyl-4-hydrazino-1H-pyrazol[3,4-d]pyrimidine (compound 4 for short)

[0107]

[0108] Dissolve compound 3 (0.1g, 0.56mmol) in 5mL of acetonitrile at normal pressure, then slowly add hydrazine hydrate (0.034g, 0.68mmol) into the mixture, stir the reactant at room temperature for 3h, and detect it with TLC until complete reaction. The reaction solution was concentrated to obtain a solid crude product, which was washed with water and reconstituted with ethyl acetate to obtain white crystal 4.

[0109] Compound 4: white solid, 198~200℃ 1 H NMR (400MHz, DMSO-d 6 )δ:8.29(s,1H,CH),8.05(s,1H,CH),4.85(s,2H,NH 2 ),4.65(s,1H,NH),4.30(dd,J=7.18Hz,J=14.38Hz,2H,CH 2 ),1.36(t,J=7.22Hz,3H,CH 3 ); 13 C NMR (100MHz, DMSO-d 6 )161.03,155.41,153.66,135.16,99.12,41.50,15.20;IR(KBr,ν,cm -1 ):1717,1659,1599,1538,1497,1441,1375,1346,1295,1251,1182,1091,962,913,860,785,694,620,541.HRMS(ESI)calcdfor C 7 h 10 N 6 [M+H] ＋ 178.0967found179.1044.

Embodiment 3

[0110] Example 31-N-ethyl-4-N-2'-(4-methylbenzenesulfonyl)hydrazine-1H-pyrazol[3,4-d]pyrimidine (referred to as compound 5a)

[0111]

[0112] Compound 4 (0.3 g, 1.69 mmol) was dissolved in 5 mL THF under normal pressure, and a good amount of pyridine (0.19 g, 2.41 mmol) was added under ice-cooling conditions, and the mixture was stirred for 1 h. Then, 4-methylbenzenesulfonyl chloride (0.39g2.05mmol) was slowly added dropwise to the mixture and continued to stir for 1h, then moved to room temperature and detected by TLC until the reaction was complete. The reaction solution was poured into 10 mL of water, adjusted to a pH of about 3 with dilute hydrochloric acid, extracted with ethyl acetate (4×20 mL), the organic layer was washed with saturated sodium chloride, dried over anhydrous magnesium sulfate, and concentrated to obtain a solid. The crude product was subjected to silica gel column chromatography, eluting with petroleum ether: acetone (2:1), to obtain white crystal 5...

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Abstract

The invention provides an allopurinol derivative shown in a formula I and a method for preparing the same. 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 clinically treating 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 uses. 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 of hyperu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/519A61P19/06A61P35/00
Inventor 尹述凡李财虎张露韵杨芳蒋丽娟李颖董林
Owner SICHUAN UNIV
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