3-oxa acridone, derivatives thereof and preparation

A technology for oxacridone and derivatives, which is applied in the field of acridone derivatives, can solve the problems such as the unsubstituent parent ring structure that has not yet been found, and achieves the effects of low cost, simple operation and low equipment investment.

Inactive Publication Date: 2009-05-27
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Some acridone compounds containing quinoline skeletons found so far contain substituents, and no parent ring structure without substituents has been found

Method used

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  • 3-oxa acridone, derivatives thereof and preparation
  • 3-oxa acridone, derivatives thereof and preparation
  • 3-oxa acridone, derivatives thereof and preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 0.023g (1mmol) sodium metal to 3mL of absolute ethanol, after it is completely dissolved, add 0.156g (1.5mmol) ethyl glycolate and react at 60°C for 5h, spin dry the white solid of the solvent, add dissolved 0.294g (1mmol) ethyl 2-bromomethyl-3-quinolinic acid in 2mL of dry benzene, react at 50°C for 12h, after the reaction is completed, cool to room temperature and add 3mL of cold water to decompose the excess sodium salt, separate the benzene layers The aqueous layer was extracted 4 times with ether, the benzene layer and the organic layer were combined and dried over anhydrous sodium sulfate, and then separated by column chromatography to obtain 0.254 g of diethyl o-carboxyquinoline methoxyacetate, with a yield of 80.1%. The melting point is 56.9-57.1°C.

[0030] Add 0.035g (1.5mmol) sodium metal to 8mL of absolute ethanol, spin the solvent after it is completely dissolved, add 2mL of dry toluene to it and raise the temperature to 120°C, then add 0.317g (1mmol) o...

Embodiment 2

[0033] Add 0.035g (1.5mmol) sodium metal to 6mL of absolute ethanol, after it is completely dissolved, add 0.321g (3mmol) ethyl glycolate and react at 40°C for 6h, spin dry the white solid of the solvent, add dissolved 0.294g (1mmol) ethyl 2-bromomethyl-3-quinolinic acid in 5mL of dry benzene, react at 60°C for 6h, after the reaction is completed, cool to room temperature and add 8mL of cold water to decompose the excess sodium salt, separate the benzene layers The aqueous layer was extracted 6 times with ether, the benzene layer and the organic layer were combined and dried with anhydrous sodium sulfate, and then separated by column chromatography to obtain 0.201 g of diethyl o-carboxyquinoline methoxyacetate, with a yield of 63.5%. The melting point is 56.7-57.1°C.

[0034] Add 0.023g (1mmol) sodium metal to 3mL of absolute ethanol, spin dry the solvent after it is completely dissolved, add 5mL of dry toluene to it and raise the temperature to 140°C, then add 0.317g (1mmol) ...

Embodiment 3

[0037] Add 0.046g (2mmol) sodium metal to 10mL of absolute ethanol, after it is completely dissolved, add 0.312g (4mmol) ethyl glycolate and react at 80°C for 4h, spin dry the white solid of the solvent, add 4mL of Dry 0.294g (1mmol) of ethyl 2-bromomethyl-3-quinolinic acid in benzene, react at 100°C for 6h, after the reaction is completed, cool to room temperature and add 6mL of cold water to decompose the excess sodium salt, and separate the benzene layer , the aqueous layer was extracted 3 times with ether, the benzene layer and the organic layer were combined and dried over anhydrous sodium sulfate, and then separated by column chromatography to obtain 0.241g of diethyl o-carboxyquinoline methoxyacetate, the yield was 76.1%, and the melting point 56.9~57.5℃.

[0038] Add 0.069g (3mmol) sodium metal to 12mL of absolute ethanol, spin the solvent after it is completely dissolved, add 3mL of dry toluene to it and raise the temperature to 90°C, then add 0.317g (1mmol) of o-carb...

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Abstract

The invention provides 3-oxa-acridone, derivatives and a preparation method thereof. The 3-oxa-acridone and the derivatives thereof have the following structural formula: in the formula, A is the 3-oxa-acridone; and B is the derivatives of the 3-oxa-acridone. The reaction process of the method for preparing the 3-oxa-acridone and the derivatives thereof is shown in a figure, wherein R1 and R2 can respectively represent hydrogen or methylenedioxy. The 3-oxa-acridone, the derivatives and the preparation method thereof have the advantages of normal pressure reaction, low requirement on temperature, small equipment investment, simple and safe operation, low cost, simple raw materials, easy synthesis, low process difficulty, convenient operation, easy product separation, and can obtain a pure product only by column chromatography separation or recrystallization. The invention synthesizes a novel 3-oxa-acridone matrix ring containing a quinoline skeleton with novel structure but without a substituent and derivatives thereof, and can be applied to synthesis of antibiosis drugs, antiphlogosis drugs, anti-tumor drugs and the like, thereby providing a matrix compound to synthesize other novel compounds.

Description

technical field [0001] The invention relates to a novel acridone derivative containing a quinoline skeleton with potentially important biopharmacological activity, in particular to a 3-oxaacridone and its derivative and a preparation method. Background technique [0002] Acridine compounds are a class of heterocyclic compounds with various pharmacological activities. Acridine and acridone compounds have anti-inflammatory, antibacterial and antimalarial properties, especially some acridone compounds have significant anticancer activity. Acridine derivatives have a wide range of pharmacological and biological activities, and have been found to have anti-malarial, anti-cancer, and antibacterial effects. Many drugs are synthesized using polyhydroacridine as a substrate. [0003] Since acridine was found to have antibacterial activity in 1912 and was used clinically in 1917, a large number of acridine compounds have been obtained from natural products or chemically synthesized, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052C07D491/153
Inventor 高文涛高峰李阳张晓飞张朝花刘华业
Owner BOHAI UNIV
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