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3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives, preparation methods and uses thereof

A xanthene and disubstituted technology, applied in the field of compounds and their preparation, can solve the problems of damage to normal cells, toxic side effects, etc.

Active Publication Date: 2013-02-27
HARBIN MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemotherapeutic drugs have relatively large toxic and side effects, inhibit tumor cells and damage normal cells at the same time, which brings great pain to cancer patients

Method used

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  • 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives, preparation methods and uses thereof
  • 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives, preparation methods and uses thereof
  • 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives, preparation methods and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of 14-(4-fluorophenyl)-14H-dibenzo[a,j]xanthene-3,11-dicarboxylic acid (2c):

[0060] Stir 3.76g (20mmol) of 6-hydroxy-2-naphthalenecarboxylic acid, 1.30g (10.5mmol) of p-fluorobenzaldehyde and 21ml of mixed acid (20ml of glacial acetic acid and 1ml of concentrated sulfuric acid) at room temperature for ten minutes, then heat to reflux for 1h, and use a thin The reaction was monitored by layer chromatography. After the reaction, the reaction system was cooled to room temperature, filtered, the precipitate was washed with acetic acid and distilled water, and dried to obtain 3.96 g of white powder, with a yield of 85.3%. Melting point: >300°C. 1 H NMR (DMSO-d 6 , 300MHz) δ: 8.77(d, J=9.0Hz, 2H, 1, 13-H), 8.62(d, J=1.4Hz, 2H, 4, 10-H), 8.16(d, J=9.0Hz, 2H, 5, 9-H), 8.07 (dd, J=9.0, 1.4Hz, 2H, 2, 12-H), 7.66 (d, J=9.0Hz, 2H, 6, 8-H), 7.68-7.59 (m, 2H, 2', 6'-H), 6.99 (t, J=8.8Hz, 2H, 3', 5'-H), 6.82 (s, 1H, 14-H).

Embodiment 2

[0061] Example 2: Preparation of 14-(4-bromophenyl)-14H-dibenzo[a,j]xanthene-3,11-dicarboxylic acid (2g):

[0062] The operation process was the same as in Example 1, except that p-bromobenzaldehyde was used instead of p-fluorobenzaldehyde to obtain a white powder (2 g), with a yield of 85.6%. Melting point: >300°C. 1H NMR (DMSO-d 6 , 300MHz) δ: 8.76 (d, J=8.8Hz, 2H, 1, 13-H), 8.63 (br.s, 2H, 4, 10-H), 8.19 (d, J=8.9Hz, 2H, 5 , 9-H), 8.07 (br.d, J=8.8, 2H, 2, 12-H), 7.68 (d, J=8.9Hz, 2H, 6, 8-H), 7.59 (d, J=6.9 Hz, 2H, 2', 6'-H), 7.37 (d, J=6.5Hz, 2H, 3', 5'-H), 6.82 (s, 1H, 14-H).

Embodiment 3

[0063] Example 3: N3,N11-bis(2-hydroxyethyl)-14-(4-fluorophenyl)-14H-dibenzo[a,j]xanthene-3,11-diamide (6Ac) Preparation of:

[0064] Add 0.93 g (2 mmol) of 14-(4-fluorophenyl)-14H-dibenzo[a,j]xanthene-3,11-dicarboxylic acid (compound 2c), 20 ml of chloroform and a drop of DMF to three In the flask, add a solution of thionyl chloride (2.2mL, 30mmol) in 8ml of chloroform dropwise, and then heat the reaction system to reflux. After reacting for 4h, evaporate the solvent to obtain the intermediate acid chloride, and then reconstitute the 20ml chloroform solution of the acid chloride Add dropwise to a solution of 2-aminoethanol (0.49g, 8mmol) in 25ml of chloroform, monitor the reaction by thin-layer chromatography, react at room temperature for 5h, filter to obtain a precipitate, wash with chloroform and distilled water successively, and then dry under reduced pressure to obtain a white solid 1.01 g, yield 92.0%. Melting point: 268-269°C. 1 H-NMR (DMSO-d 6 , 300MHz) δ: 8.75(d,...

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Abstract

The present invention discloses a new class of 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives, and preparation methods thereof, and belongs to the field of chemical synthesis. According to the present invention, 6-hydroxy-2-naphthalene carboxylic acid and aromatic aldehyde are adopted as raw materials, and a series of reactions are performed to synthesize a series of 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives. The present invention further provides applications of the 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]xanthene derivatives in antitumor drug preparation. With the present invention, in vitro pharmacological activity screening experiment results show that the synthesized compounds provide proliferation inhibition effects for tumor cells, wherein part of the compounds have significant inhibition effects, and IC50 is less than 1 mum; in vivo experiment results show that part of the compounds can provide animal tumor growth inhibition effects; and the derivatives have characteristics of rational design, simple preparation method and strong practicality.

Description

technical field [0001] The present invention relates to a compound and its preparation method and application, in particular to the preparation method and application of 3,11-disubstituted-14-aryl-14H-dibenzo[a,j]oxanthene derivatives, It belongs to the field of chemical synthesis. Background technique [0002] In recent years, the mortality rate of malignant tumor patients in my country has continued to rise, and the mortality rate of many common malignant tumors is relatively high. Traditional chemotherapeutic drugs have relatively large toxic and side effects, inhibit tumor cells and damage normal cells at the same time, which brings great pain to cancer patients. Therefore, obtaining high-efficiency and low-toxic antitumor drugs has been the focus of many researchers. [0003] The synthesis of xanthenes, especially dibenzoxanthenes, is the focus of current research, mainly due to the wide range of physiological and pharmacological activities of these compounds, such as...

Claims

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Application Information

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IPC IPC(8): C07D311/78A61P35/00A61P35/02
Inventor 杨宝峰侯云龙王立波吴立军董德利宋永彬刘波
Owner HARBIN MEDICAL UNIVERSITY
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