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4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-l-xylofuranose)pyrrolo[2, 3-d]pyrimidine, similar derivatives And for the preparation of antitumor drugs

A technology of xylofuranose and bromophenyl, which is applied in the field of new drug synthesis, can solve the problems of poor cell membrane permeability, failure to achieve, and short half-life in vivo

Inactive Publication Date: 2011-12-21
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds have defects such as poor cell membrane permeability and short half-life in vivo, and have not achieved the expected clinical effect.

Method used

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  • 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-l-xylofuranose)pyrrolo[2, 3-d]pyrimidine, similar derivatives And for the preparation of antitumor drugs
  • 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-l-xylofuranose)pyrrolo[2, 3-d]pyrimidine, similar derivatives And for the preparation of antitumor drugs
  • 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-l-xylofuranose)pyrrolo[2, 3-d]pyrimidine, similar derivatives And for the preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Synthesis of 4-amino-6-bromo-5-cyanopyrrole [2,3-d] pyrimidine A

[0047] (1) Dissolve tetracyanoethylene (14.5g, 113mmol) in acetone (81mL) and ethyl acetate (171mL), add dropwise to this solution a solution of hydrobromic acetic acid (81mL) with a mass concentration of 33%, and keep the internal Temperature 0°C. Continue stirring for 3 hours after the dropwise addition, and suspend the obtained solid in water after filtration, add concentrated ammonia water to adjust the pH value to 9, then treat it with glacial acetic acid until the pH value is 5, collect the precipitate by filtration, and obtain 18.6 g of off-white solid after drying. Yield 78%.

[0048] (2) The above off-white solid (10.50 g, 0.10 mol) and formamidine acetate (10.50 g, 0.10 mmol) were dissolved in ethylene glycol diethyl ether (100 mL). Heated to reflux for 12h, the filtrate was cooled to room temperature, a brown precipitate was produced, and the crude product was obtained by suction ...

Embodiment 2

[0049] Example 2: Synthesis of 1-O-acetyl-2,3,5-tri-O-benzoyl-L-xylose (B)

[0050] Suspend L-xylose (4.5g, 30mol) in ethanol (70mL), add H 2 SO 4 (0.3mL), stirred at room temperature for 5h, added anhydrous K 2 CO 3 Adjusted to neutral, after filtration, the filtrate was distilled under reduced pressure to remove the solvent. Toluene was added to the residue to remove water azeotropically to obtain 4.95 g of the crude product, which was dissolved in tetrahydrofuran (100 mL), and benzoyl chloride (10.47 mL, 90 mol) was added with stirring in an ice bath, and stirred overnight at room temperature. The solvent was distilled off under reduced pressure, and the residue was extracted with water and chloroform. The organic layer was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, filtered, and evaporated to remove the solvent under reduced pressure to obtain 13.8 g of crude brown oil, which was directly used in the next step.

[0051] Glacial ac...

Embodiment 3

[0052] Example 3: 4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-benzoyl-β-L-xylofuranose)pyrrole[2,3-d] Synthesis of pyrimidine

[0053] Under stirring at room temperature, BSA (4.1 g , 20mmol). After 30 minutes, 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-xylose 2 (5.0 g, 10 mmol) in Example 2 was added, followed by trifluoroform Silica-based (TMSOTf, 3.33 g, 5 mmol). Stir at room temperature for 10 minutes, heat at 60°C for 3 hours, then cool to room temperature. After the reaction was completed, it was diluted with 100mL ethyl acetate and 50mL water. The organic layer was washed successively with sodium bicarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was purified by column chromatography, using ethyl acetate: chloroform (1:5, v / v) as the eluent to obtain 4-amino-6-bromo-5-cyano-7-( 5.1 g of 2,3,5-tri-O-benzoyl-β-L-xylfuranose)pyrrole[2,3-d]pyrimidine, yield 73%. m.p.150-152℃.MS(ESI):m / z...

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Abstract

The invention belongs to the technical field of new drug synthesis, in particular to a class of 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-L-xylofuranose)pyrrolo [2,3-d]pyrimidine, its similar derivatives, and drugs for preparing anti-human liver cancer cells, human lung cancer cells, human breast cancer cells, human cervical cancer cells, and human gastric cancer cells. The compounds of the present invention are directed against 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-L-xylofuranose)pyrrolo[2,3 -d] The C6 position of pyrimidine is modified and synthesized by chemical methods. Experiments have shown that this type of compound can significantly inhibit the proliferation of various cancer cells, effectively induce apoptosis of cancer cells, including highly metastatic cancer cells, and can be used as drugs and drug components for treating cancer.

Description

technical field [0001] The invention belongs to the technical field of new drug synthesis, in particular to a class of 4-amino-6-(3-(3-bromophenyl)phenyl)-5-cyano-7-(β-L-xylofuranose)pyrrolo [2,3-d]pyrimidine, its similar derivatives and medicines for preparing anti-liver cancer, lung cancer, breast cancer, cervical cancer and gastric cancer. Background technique [0002] Most of the anticancer drugs currently used clinically hinder the growth of cancer cells by directly or indirectly inhibiting DNA synthesis. Cancer cells are genetically unstable and resistant to the inhibitory effect of DNA synthesis, leading to cancer recurrence. At the same time, the inhibition of DNA synthesis is often accompanied by relatively large side effects. Therefore, it is crucial to develop cancer cell-specific anticancer drugs. [0003] The hyperactivity of cell cycle and the blockage of apoptosis lead to cell canceration. Upregulation of the activity of cell cycle-dependent kinases (Cdks)...

Claims

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Application Information

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IPC IPC(8): C07H19/14C07H1/00A61K31/7064A61P35/00
Inventor 金英花宋志光孙超肖川李扬朱丹
Owner JILIN UNIV
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