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Beta-carboline dimer salt compounds and application of beta-carboline dimer salt compounds in preparation of drugs used for preventing or treating tumour

A technology of salt compound and carboline dimer, which is applied in the field of preparation of β-carboline dimer salt compound, can solve the problems of tumor treatment failure and achieve strong inhibitory effect

Inactive Publication Date: 2015-04-08
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of effective anti-tumor drugs have been developed, the failure of treatment will be caused by tumor metastasis and drug resistance. Therefore, the continuous development of new anti-tumor drugs is of great significance

Method used

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  • Beta-carboline dimer salt compounds and application of beta-carboline dimer salt compounds in preparation of drugs used for preventing or treating tumour
  • Beta-carboline dimer salt compounds and application of beta-carboline dimer salt compounds in preparation of drugs used for preventing or treating tumour
  • Beta-carboline dimer salt compounds and application of beta-carboline dimer salt compounds in preparation of drugs used for preventing or treating tumour

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of 2-[4-(β-carboline-2-yl)butyl]-β-carboline dibromide:

[0039] Weigh β-carboline (1mmol) into a 50mL round bottom flask, add 20mL of isopropanol and 1,4-dibromobutane (0.5mmol), reflux reaction at 85°C, detect the reaction by TLC every 2h, after 24h The reaction was stopped, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain the target compound (0.44 mmol, yield: 44%). 1 H-NMR (500MHz, DMSO-d 6 ): δ8.68 (2H, d, J = 6.6Hz), 8.62 (2H, s), 8.34 (2H, d, J = 6.6Hz), 8.22 (2H, d, J = 8.8Hz), 7.68 (2H , d, J=8.2Hz), 7.53 (2H, m), 7.13 (2H, m), 4.70 (4H, t), 3.46 (2H, s), 1.92-1.94 (4H, m); 13 C-NMR (500MHz, DMSO-d 6 ): δ151.4, 141.1, 138.6, 136.1, 134.60, 132.5, 126.05, 123.2, 118.9, 117.2, 99.8, 65.9, 26.3; ESI-MS m / z: 473.1 [M-Br] + .

Embodiment 2

[0041] Synthesis of 2-[5-(β-carboline-2-yl)pentyl]-β-carboline dibromide:

[0042] Weigh β-carboline (1mmol) into a 50mL round bottom flask, add 20mL of isopropanol and 1,5-dibromopentane (0.5mmol), reflux reaction at 85°C, check the reaction by TLC every 2h, after 24h The reaction was stopped, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain the target compound (0.38 mmol, yield: 38%). 1 H-NMR (500MHz, DMSO-d6): δ8.68 (2H, d, J = 6.6Hz), 8.62 (2H, s), 8.34 (2H, d, J = 6.6Hz), 8.22 (2H, d, J=8.8Hz), 7.68(2H, d, J=8.2Hz), 7.53(2H, m), 7.13(2H, m), 4.70(4H, t), 3.46(2H, s), 1.98-2.02( 4H, m), 1.72-1.75 (2H, m); 13 C-NMR (500MHz, DMSO-d6): δ151.4, 141.1, 138.6, 136.1, 134.60, 132.5, 126.05, 123.2, 118.9, 117.2, 99.8, 65.9, 29.3, 18.9; ESI-MSm / z: 487.1 [M -Br] + .

Embodiment 3

[0044] Synthesis of 1-methyl-2-[p-(β-carboline-2-yl)benzyl]-β-carboline dibromide:

[0045] Weigh 1-methyl-β-carboline (1mmol) into a 50mL round bottom flask, add 20mL of isopropanol and α,α'-dibromo-p-xylene (0.5mmol), reflux at 85°C, every 2h The reaction was detected by TLC. After 24 hours, the reaction was stopped, concentrated under reduced pressure, and separated by silica gel column chromatography to obtain the target compound (0.41 mmol, yield: 41%). 1 H-NMR (500MHz, DMSO-d 6): δ8.70 (2H, d, J = 6.6Hz), 8.64 (2H, d, J = 6.6Hz), 8.22 (2H, d, J = 8.8Hz), 7.68 (2H, d, J = 8.2Hz ), 7.53(2H, m), 7.10(4H, s), 7.13(2H, m), 6.42(4H, t), 3.46(2H, s), 2.98(6H, s); 13 C-NMR (500MHz, DMSO-d 6 ): δ148.23, 142.76, 139.12, 132.60, 131.3, 130.32, 126.05, 123.2, 117.9, 117.2, 113.8, 113.67, 99.8, 58.8, 29.5; ESI-MS m / z: 549.2 [M-Br] + .

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Abstract

The invention relates to beta-carboline dimer salt compounds and application of the beta-carboline dimer salt compounds in preparation of drugs used for preventing or treating tumour. A structural formula of the beta-carboline dimer salt compounds is shown in a formula I. The beta-carboline dimer salt compounds have a strong inhibiting effect on growth of tumour cells, and activity of the beta-carboline dimer salt compounds is close to that of a positive control paclitaxel; meanwhile, anti-tumour activity of parts of the beta-carboline dimer salt compounds is obviously better than that of paclitaxel, and the IC50 value is less than 1mu M, so that the beta-carboline dimer salt compounds can become efficient candidate drugs used for treating tumour. The formula (I) is described in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of a class of β-carboline dimer salt compounds and an antitumor application. Background technique [0002] Tumor (especially malignant tumor) is one of the main diseases that threaten human health and life. Although a variety of effective anti-tumor drugs have been developed, the failure of treatment will be caused by tumor metastasis, drug resistance and other reasons. Therefore, the continuous development of new anti-tumor drugs is of great significance. It is an important way to discover high-efficiency and low-toxic anti-tumor drugs by taking natural-sourced active ingredients with anti-tumor activity as lead compounds and modifying their structures. . Contents of the invention [0003] Aiming at the defects or deficiencies of the prior art, the present invention provides a β-carboline dimer salt compound, the general structura...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00A61K31/437A61P35/00A61P35/02
CPCC07D519/00
Inventor 王俊儒杜宏涛李娜谷红玲秦文娟
Owner NORTHWEST A & F UNIV