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6-(beta-alkylnaphthy)mercaptopurine compound, and synthesis method and application thereof

A technology of mercaptopurine and synthetic method, which is applied in organic chemistry, drug combination, antineoplastic drugs, etc., to achieve remarkable effect, simple synthesis steps and high yield

Inactive Publication Date: 2013-09-25
JILIN PROVINCE SCI & TECH EVALUATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And 6-(β-alkylnaphthalene) mercaptopurine compound and its synthetic method and application have not yet been reported

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  • 6-(beta-alkylnaphthy)mercaptopurine compound, and synthesis method and application thereof
  • 6-(beta-alkylnaphthy)mercaptopurine compound, and synthesis method and application thereof
  • 6-(beta-alkylnaphthy)mercaptopurine compound, and synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] 1. Synthesis of 6-(β-methylnaphthalene) mercaptopurine compound

[0025] (1) In an inert gas atmosphere, anhydrous and oxygen-free reactor, add the solvent N,N-dimethylacetamide dissolved in 6-mercaptopurine, the mass fraction of 6-mercaptopurine is 0.34 parts, N , the mass fraction of N-dimethylacetamide is 10 parts;

[0026] (2) Add 0.7 parts of potassium carbonate and 0.53 parts of 2-bromomethylnaphthalene to the above reactor in turn, and react at room temperature for 4.5 hours;

[0027] (3) After the reaction is completed, add 10 parts of deionized water to the above system, and then add acetic acid for neutralization to form a precipitate;

[0028] (4) Remove the supernatant of the above mixture, and then wash the precipitate with deionized water and ether respectively to obtain a crude product of white solid, which is recrystallized with the solvent toluene to obtain the final product 6-(β- Methylnaphthalene) mercaptopurine compound, the productive rate is 66.5...

Embodiment 2

[0037] 1. Synthesis of 6-(β-ethylnaphthalene) mercaptopurine compound

[0038] (1) In an inert gas atmosphere, anhydrous and oxygen-free reactor, add the solvent N,N-dimethylacetamide dissolved in 6-mercaptopurine, the mass fraction of 6-mercaptopurine is 1, the solvent N , the mass fraction of N-dimethylacetamide is 20 parts;

[0039] (2) Add 1 part of potassium carbonate and 1.2 parts of 2-bromoethylnaphthalene to the above reactor in turn, and react at room temperature for 7 hours;

[0040] (3) After the reaction is completed, add 25 parts of deionized water to the above system, and then add acetic acid for neutralization to form a precipitate;

[0041] (4) Remove the supernatant of the above mixture, and then wash the precipitate with deionized water and ether respectively to obtain a crude product of a white solid, which is recrystallized with the solvent xylene to obtain the final product 6-(β -ethylnaphthalene) mercaptopurine compound, the productive rate is 72.18%. ...

Embodiment 3

[0045] 1. Synthesis of 6-(β-methylnaphthalene) mercaptopurine compound

[0046] (1) In an inert gas atmosphere, anhydrous and oxygen-free reactor, add the solvent N,N-dimethylacetamide dissolved in 6-mercaptopurine, the mass fraction of 6-mercaptopurine is 0.6 parts, N, The mass fraction of N-dimethylacetamide is 10 parts;

[0047](2) Add 0.7 parts of potassium carbonate and 0.8 parts of 2-bromomethylnaphthalene to the above reactor in turn, and react at room temperature for 4.5 hours;

[0048] (3) After the reaction is completed, add 17 parts of deionized water to the above system, and then add acetic acid for neutralization to form a precipitate;

[0049] (4) Remove the supernatant of the above mixture, and then wash the precipitate with deionized water and ether respectively to obtain a crude product of white solid, which is recrystallized with the solvent toluene to obtain the final product 6-(β- Methylnaphthalene) mercaptopurine compound, the productive rate is 69.64%. ...

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Abstract

The invention discloses a 6-(beta-alkylnaphthy)mercaptopurine compound of which the structural formula is disclosed in the specification. The 6-(beta-alkylnaphthy)mercaptopurine compound can inhibit growth of cancer cells. The invention also discloses a synthesis method and application of the 6-(beta-alkylnaphthy)mercaptopurine compound. The synthesis method has the advantages of simple synthesis steps and higher yield, and is suitable for industrial production. The 6-(beta-alkylnaphthy)mercaptopurine compound disclosed by the invention is used for inhibiting cancer cells, and has obvious effect.

Description

field of invention [0001] The invention belongs to the field of pharmaceutical chemical synthesis, and in particular relates to a 6-(β-alkylnaphthalene) mercaptopurine compound and its synthesis method and application. Background technique [0002] Cancer, also known as malignant tumor, is a disease caused by the abnormal mechanism of controlling cell growth and proliferation. In addition to growing out of control, cancer cells can also locally invade the surrounding normal tissues and even transfer to other parts of the body through the internal circulatory system or lymphatic system. Therefore, the exploration of antitumor drugs has always been one of the hot spots in the research and development of new drugs. 6-Mercaptopurine is an antimetabolite drug with immunosuppressive effect that interferes with nucleic acid synthesis by inhibiting purine metabolism. Commonly used in anti-tumor and transplant rejection. Its structure is similar to that of hypoxanthine, and it can...

Claims

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Application Information

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IPC IPC(8): C07D473/38A61P35/00
Inventor 姜鑫刘宏博李晓萌祝洪艳李占东
Owner JILIN PROVINCE SCI & TECH EVALUATION
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