Bibenzyl ether compound as well as preparation method and application thereof

A compound and solvate technology, applied in the field of bibenzyl ether compounds and their preparation, can solve the problems of no bibenzyl ether compound research reports and no bibenzyl ether compound antitumor drug research reports, etc. Achieve significant inhibition of activity, high yield, and low energy consumption

Inactive Publication Date: 2017-03-15
CHENGDU UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there is no research report on the bibenzyl ether compounds shown in the formula I of the present invention, and there is no research report on the use of the bibenzyl ether compounds shown in the formula I of the present invention for the preparation of antitumor drugs

Method used

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  • Bibenzyl ether compound as well as preparation method and application thereof
  • Bibenzyl ether compound as well as preparation method and application thereof
  • Bibenzyl ether compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1. Extraction and structural identification of bibenzyl ether compounds of the present invention

[0089] (1) Extraction of medicinal materials:

[0090] Dried white and medicinal material coarse powder (3kg), reflux extraction with 95% ethanol 3 times (30L×3), 2h each time;

[0091] (2) Separation and purification of components:

[0092] 1. Ethanol extract (90L) was concentrated and dried under reduced pressure to obtain 510g of semi-solid liquid extract;

[0093] ②. Disperse the semi-solid liquid extract (500g) with water (5L), extract with ethyl acetate (20L) and n-butanol (20L) successively, combine the ethyl acetate part, recover the solvent under reduced pressure, and obtain ethyl acetate leaching Cream 160g;

[0094] 3. Adopt silica gel column chromatography to separate ethyl acetate extract (160g), petroleum ether: acetone carries out gradient elution, and the eluent is detected by thin-layer chromatography, and obtains the elution when petroleum ethe...

Embodiment 2

[0112] Example 2, the anti-lung cancer A549 activity test of the bibenzyl ether compounds of the present invention

[0113] ① Cell inoculation

[0114] Cells in logarithmic growth phase were digested with 0.25% trypsin. Cultured in cell culture medium containing 10% FBS to form a single cell suspension. The A549 tumor cells in good condition were inoculated in a 96-well plate by counting with a cell counting plate, so that the cell density was 4×10 3 cells / mL, add 100 μL of cell suspension to each well, place at 37°C, 5% CO 2 Cultivate in the incubator for 24h.

[0115] ②, drug treatment

[0116] Starting from 10 μg / mL for each sample, dilute the sample with medium gradient, 2-fold dilution, set 5 drug concentrations, and do a duplicate hole test for each concentration. Add 100 μL of drug to each well at a concentration of 10, 5, 2.5, 1.25, 0.625 μg / mL, set 3 replicate wells for each concentration, and repeat 3 times. The negative control group is a medium solution conta...

Embodiment 3

[0121] Embodiment 3, anti-acute monoleukemia MV4-11 activity test of bibenzyl ether compounds of the present invention

[0122] ① Cell inoculation

[0123] Cells in logarithmic growth phase were digested with 0.25% trypsin. Cultured in cell culture medium containing 10% FBS to form a single cell suspension. The MV4-11 cells in good condition were inoculated in a 96-well plate by counting with a cell counting plate, so that the cell density was 2×10 4 cells / mL, add 100 μL of cell suspension to each well, place at 37°C, 5% CO 2 Cultivate in the incubator for 24h.

[0124] ②Drug treatment

[0125] Starting from 50 μg / mL for each sample, dilute the sample with culture medium step by step, 2-fold dilution, set 5 drug concentrations, and do a duplicate hole test for each concentration. Add 100 μL of drug to each well at the concentration of 50, 25, 12.5, 6.25, 3.125 μg / mL, set 3 replicate wells for each concentration, and repeat 3 times. The negative control group is a medium ...

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Abstract

The invention discloses a compound shown in the formula I or pharmaceutically acceptable salts, crystal forms and solvates thereof, wherein R1, R2, R3, R4, R5, R6 and R7 are respectively and independently selected from H, hydroxyl, sulfydryl, C1-C4 alkyl or C1-C4 alkoxy. A bibenzyl ether compound disclosed by the invention simultaneously has a bibenzyl structure and a diphenyl ether structure, and compared with the conventional bibenzyl compound, the bibenzyl ether compound has great difference in the structure; in addition, the bibenzyl ether compound disclosed by the invention has a new efficacy: a good inhibiting effect on tumor cells, in particular to a good inhibiting effect to lung cancer cells, wherein IC50 reaches 3.9mug / mL; additionally, the bibenzyl ether compound disclosed by the invention has the obvious inhibiting activity for proliferation of acute leukemia cells.

Description

technical field [0001] The invention relates to a bibenzyl ether compound and its preparation method and application. Background technique [0002] The existing literature reports that the following bibenzyl compounds have the efficacy and use of inhibiting passive cutaneous anaphylaxis and inhibiting the release of β-hexosaminidase from RBL-2H3 cells (basophilic leukemia cells) (See: Matsuda H et al. Antiallergic Phenanthrenes and... Planta Med 2004; 70:847-855): [0003] [0004] At present, there is no research report on the bibenzyl ether compound represented by the formula I of the present invention, and there is no research report on the use of the bibenzyl ether compound represented by the formula I of the present invention to prepare antitumor drugs. Contents of the invention [0005] The object of the present invention is to provide a new bibenzyl ether compound with different structure and medicinal value: the compound represented by formula I. [0006] The ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/295C07C41/34C07C41/36C07C41/38A61K31/09A61P35/00A61P35/02
CPCC07C41/34C07C41/36C07C41/38C07C43/295
Inventor 彭成戴鸥熊亮仰莲郭力
Owner CHENGDU UNIV OF TRADITIONAL CHINESE MEDICINE
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