12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and synthesis method thereof

A methylene dioxy and synthetic method technology is applied in the field of acridone derivatives and achieves the effects of easy availability of raw materials, simple operation and good absorption

Inactive Publication Date: 2015-05-13
XINXIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The innovation of the present invention lies in the synthesis of a methylenedioxyacridone compound containing a fluorine atom. This compound has not been reported yet. According to preliminary pharmacological activity measurements, this compound has strong anticancer activity

Method used

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  • 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and synthesis method thereof
  • 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and synthesis method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Put 1.37g of 3,4-methylenedioxyaniline, 1.24g of 2-fluorobenzaldehyde, 1.74g of 2-hydroxy-1,4-naphthoquinone and 0.2g of p-toluenesulfonic acid in a 50mL reaction flask and mix well , heated and stirred, and the temperature was controlled at 115°C. After reacting for 5 hours, the reaction mixture was dissolved with 20mL of dichloromethane, washed twice with 20mL of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, washed twice with 20mL of ethanol, and filtered to obtain orange The red corresponding product 12-(2-fluorophenyl)-benzo[ h ][1,3] Methylenedioxy[4,5- b ] Acridine-10,11-dione 3.57g, the yield is 90%.

[0018] After testing, molecular formula: C 24 h 14 NO 4 , Molecular weight: 397.08, Appearance: orange-yellow solid, Melting point: 280-281°C;

[0019] IR (KBr): v 3069, 2921, 1682, 1541, 1462, 1435, 1259, 1207, 1170, 1033, 942, 861, 769cm -1 ;

[0020] 1 H NMR (400MHz, DMSO- d 6 ) δ : 8.83 (d, 1H, J = 7.6Hz, ArH), 8.0...

Embodiment 2

[0025] Put 6.85g of 3,4-methylenedioxyaniline, 6.82g of 2-fluorobenzaldehyde, 8.70g of 2-hydroxy-1,4-naphthoquinone and 1g of p-toluenesulfonic acid in a 100mL reaction flask and mix evenly. Heat and stir with the temperature controlled at 125°C. After 4 hours of reaction, the reaction mixture was dissolved in 100mL of dichloromethane, washed twice with 100mL of water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, washed twice with 100mL of ethanol, and filtered to obtain orange-red The corresponding product 12-(2-fluorophenyl)-benzo[ h ][1,3] Methylenedioxy[4,5- b ] Acridine-10,11-dione 18.26g, the yield is 92%.

Embodiment 3

[0027] Put 13.70g of 3,4-methylenedioxyaniline, 12.4g of 2-fluorobenzaldehyde, 17.40g of 2-hydroxy-1,4-naphthoquinone and 2g of p-toluenesulfonic acid in a 250mL reaction flask and mix well. Heat and stir with the temperature controlled at 130°C. After reacting for 3 hours, dissolve the reaction mixture with 200mL of dichloromethane, wash twice with 200mL of water, dry over anhydrous sodium sulfate, evaporate the solvent, wash twice with 200mL of ethanol, and filter to obtain orange-red The corresponding product 12-(2-fluorophenyl)-benzo[ h ][1,3] Methylenedioxy[4,5- b ] Acridine-10,11-dione 34.94g, the yield is 88%.

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Abstract

The invention discloses 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and a synthesis method thereof, and belongs to the technical field of dihydroketoacridine derivatives. The method comprises the steps of uniformly mixing 3,4-methylenedioxy aniline, 2-fluorobenzaldehyde, 2-hydroxyl-1,4-naphthaquinone, a catalyst and toluene sulfonic acid, performing heating and stirring, controlling the temperature to be 115-130 DEG C, and performing a reaction for 3-5h. Fluorine atom and methylenedioxy structures are introduced into 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone, so that 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone has higher activity, and more facilitates absorption. The synthesis method has the characteristics that the synthesis method is simple to operate, high in yield, green and environment-friendly, and raw materials are easy to obtain.

Description

technical field [0001] The invention belongs to the technical field of acridone derivatives, in particular to a 12-(2-fluorophenyl)-benzo[ h ][1,3]methylenedioxy[4,5- b ] Acridine-10,11-dione and its synthesis method. Background technique [0002] Malignant tumor is one of the important diseases that endanger human health at present. It is the first killer of human beings in the new century and poses the most serious threat to human survival. The development and research of new and effective anti-tumor drugs is a major topic and long-term task in the field of biomedical research. . According to literature reports, many acridone compounds have good physiological and pharmacological activities, among which 3,4-dihydro-2H-acridone has obvious killing effect on staphylococcus and yeast, 9-amino-3 , 4-dihydro-2H-acridone derivatives have the physiological activity of enhancing memory, and especially important is the synthesis of acridone with regard to anticancer efficacy, whi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056A61P35/00
CPCC07D491/056
Inventor 杨晓娟武利强
Owner XINXIANG UNIV
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