4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof

A technology of trimethoxy and chalcone is applied in the field of new compound synthesis and pharmaceutical application, and achieves the effects of high yield, mild reaction conditions and simple operation

Pending Publication Date: 2014-06-25
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, based on the C-C coupling of the chalcone benzene ring, there are rel...

Method used

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  • 4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof
  • 4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof
  • 4,2',4'-triethoxy-5' substituted chalcone derivatives and preparation method and application thereof

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Experimental program
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Embodiment 1

[0036] R is p-methoxyphenyl, that is, 4,2',4'-trimethoxy-5'(p-methoxyphenyl)chalcone. The preparation steps are as follows

[0037] (1) Synthesis of intermediate 2,4-dimethoxyacetophenone

[0038] AlCl 3 (25g, 159.23mmol) was dissolved in 150mL of anhydrous dichloromethane, the system was protected with argon, and acetyl chloride (15g, 188.18mmol) was slowly added dropwise under ice bath conditions with constant pressure drops, until all the acetyl chloride was added dropwise After completion, m-xylylene dimethyl ether (20 g, 144.8 mmol,) was dissolved in 10 mL of anhydrous dichloromethane, and slowly dropped into the reaction system through a constant pressure dropping device. Stir at room temperature for 3-4h. After the completion of the reaction was monitored by TLC, the reaction system was poured into ice water to quench acetyl chloride. Extracted 3 times with 50mL DCM, combined the organic phases, washed the organic phases with 5% sodium hydroxide twice, dried the orga...

Embodiment 2

[0050] R is p-fluorophenyl, that is, 4,2',4'-trimethoxy-5'(p-fluorophenyl)chalcone is synthesized as follows:

[0051] 4,2',4'-Trimethoxy-5'iodochalcone (200 mg, 471.44 μmol), dissolved in 1.5 mL dimethylsulfoxide. Add p-fluorophenylboronic acid (79.2mg, 565.73μmol), anhydrous potassium acetate (92.5mg, 942.89μmol), catalyst [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride ( 17mg, 23.57μmol), argon protection. Microwave at 90°C for 1.5h. After the completion of the reaction was monitored by TLC thin layer chromatography, water was added, 20 mL each of ethyl acetate was added, extracted 3 times, the organic phases were combined, dried over anhydrous sodium sulfate, evaporated to dryness, purified by silica gel column chromatography (petroleum ether: ethyl acetate = 8:1) to obtain 110 mg of yellow solid 4,2',4'-trimethoxy-5'(p-fluorophenyl)chalcone, with a yield of 58%.

[0052] 1 HNMR (400MHz, CDCl 3 ):δ / ppm3.85(s,3H),3.90(s,3H),3.99(s,3H),6.57(s,3H),6.92(d,J=8.4...

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Abstract

The invention relates to 4,2',4'-triethoxy-5' substituted chalcone derivatives, a preparation method and application of the derivatives to an antitumor medicines. Two compounds refer to 4,2',4'-triethoxy-5' (p-methoxyphenyl) chalcone and 4,2',4'-triethoxy-5' (p-fluorophenyl) chalcone. Two 4,2',4'-triethoxy-5' substituted chalcone derivatives are synthesized for the first time, and the in-vitro tumor cell inhibiting activities of the derivatives are tested. As indicated by results, the derivatives have high inhibiting activity to human erythroleukemia cells (K562) and human colon cancer cells (HT-29).

Description

technical field [0001] The invention belongs to the field of new compound synthesis and drug application, and in particular relates to a novel 4,2',4'-trimethoxy-5' substituted chalcone derivative and a preparation method thereof, and its application in antitumor drugs Applications. Background technique [0002] Chalcones are a class of compounds mainly produced by cross-aldol condensation of aromatic aldehydes and ketones, and their structures contain 1,3-diphenylpropenone structures. [0003] Its 1,3-diphenylpropenone structure determines that it has many substitution sites, and derivatives with different substituent groups at different sites have various pharmacological properties. In the known literature reports, in the synthesis of chalcone derivatives, most of them are based on the hydroxyl groups at different positions to form C-O coupling derivatives. However, based on the C-C coupling of the chalcone benzene ring, there are relatively few reports on the direct con...

Claims

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Application Information

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IPC IPC(8): C07C49/84C07C45/68A61K31/12A61P35/00A61P35/02
CPCC07C49/84C07C45/46C07C45/63C07C45/64C07C45/74
Inventor 郁彭陈哲民王浩猛杨尧宋彬彬芦逵
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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