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Hexacyclic piperazinedione compound and preparation, biological activity and application thereof

A piperazine, diketone technology, applied in the fields of anti-tumor growth, anti-tumor cell migration and invasion, and anti-tumor metastasis

Inactive Publication Date: 2020-12-01
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is still no drug that can effectively treat tumor metastasis in clinical practice.

Method used

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  • Hexacyclic piperazinedione compound and preparation, biological activity and application thereof
  • Hexacyclic piperazinedione compound and preparation, biological activity and application thereof
  • Hexacyclic piperazinedione compound and preparation, biological activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019]Example 1 Preparation of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1)

[0020]Add 0.1 mL of concentrated sulfuric acid (98%) to 200 mL of distilled water at 0°C and stirring, then add 2.04 g (10.0 mmol) of L-Trp and stir until the solid is dissolved, and finally add 5 mL of aqueous formaldehyde solution (37%) and stir at room temperature for 6 hours. TLC showed that L-Trp disappeared completely. Ammonia solution (25%) was added to the reaction mixture at 0°C while stirring to adjust the pH to 7. The reaction mixture was allowed to stand at room temperature for 30 min, and the resulting precipitate was collected by filtration to obtain 2.03 g (93%) of the title compound as a pale yellow solid. ESI-MS(m / e):217[M+H]+;1H NMR(300MHz, DMSO-d6): δ / ppm=12.141(s,1H), 10.944(s,1H),7.436(s,1H),7.321(s,1H),7.032(d,2H), 4.207(m,3H), 2.822( m,2H).

Embodiment 2

[0021]Example 2 Preparation of 3S-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2)

[0022]To 0.972 g (4.5 mmol) of 3S-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1), 10 mL of N,N-dimethylformamide was added, and the solid was suspended by stirring. Add 1.275g (1.3mmol) (Boc) to the suspension at 0℃ and stirring2O, then add triethylamine to adjust the pH to 10. The resulting solution was stirred at room temperature until TLC showed that compound 1 disappeared completely. The reaction mixture was concentrated under reduced pressure, and the obtained pale yellow oil was dissolved in 40 mL of ethyl acetate. The obtained ethyl acetate solution was washed with 5% potassium hydrogen sulfate aqueous solution (50 mL×3) and then with saturated sodium chloride aqueous solution (50 mL×3). 3), the ethyl acetate layer was dried with anhydrous sodium sulfate for 12h. After filtration, the filtrate was concentrated under reduced pressure, and the obtained light yellow ...

Embodiment 3

[0023]Example 3 Preparation of 6S-4,5,6,7-tetrahydro-imidazole[4:5]piperidine-6-carboxylic acid (3)

[0024]0.4 mL of concentrated sulfuric acid (98%) was added to a solution of 2.50 g (16.1 mmol) of L-His and 10 mL of distilled water at 0° C. and stirring to gradually dissolve L-His. Add 3 mL of aqueous formaldehyde solution (37%) to the resulting solution and heat it at 60°C for 6 h. TLC showed that L-His disappeared completely. The reaction mixture was stirred at 0°C, and then 25% aqueous ammonia solution was added to adjust the pH to 7. Let stand for 30min at room temperature and filter. The collected solid was washed three times with water and acetone each to obtain 2.649 g (98%) of the title compound as a colorless solid. ESI-MS(m / e):168[M+H]+;1H NMR(300MHz, DMSO-d6): δ / ppm=12.016(s, 1H), 7.548(s, 1H), 5.040(d, J=13.8Hz, 1H), 4.789(d, J=14.1Hz, 1H), 4.277(m, 1H) , 3.761(m,2H).

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PUM

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Abstract

The invention discloses a hexacyclic piperazinedione compound as shown in the following formula: tetrahydro-beta-carboline [3: 4] piperazine-2, 5-diketopiperidine [4: 5] imidazole. The invention discloses a preparation method and application thereof. The compound not only has an anti-tumor proliferation effect, but also can inhibit migration and invasion of tumor cells, and also has an in-vivo anti-metastasis effect.

Description

Technical field[0001]The present invention relates to tetrahydro-β-carboline [3:4]piperazine-2,5-diketopiperidine [4:5]zimidazole, its preparation method, and its anti-tumor growth effect. It further relates to its anti-tumor cell migration and invasion and anti-tumor metastasis effects. Therefore, the present invention relates to tetrahydro-β-carboline [3:4] and piperazine-2,5-diketopiperidine [4:5] and imidazole of the following formula in the preparation of anti-tumor drugs, anti-tumor metastasis drugs and Application in anti-tumor and anti-tumor metastasis drugs. The invention belongs to the field of biomedicine.Background technique[0002]Tumors have become a common disease that seriously threatens human health. For example, there were approximately 3.929 million new tumor patients in 2015, of which 2.338 million tumor patients died. On average, more than 10,000 people are diagnosed with tumors every day. Tumor metastasis, especially the metastasis of tumors to the lungs, has cau...

Claims

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Application Information

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IPC IPC(8): C07D471/22A61P35/00A61P35/04
CPCA61P35/00A61P35/04C07D471/22
Inventor 赵明彭师奇桂琳郝媛萌
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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