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Licochalcone A thiouracil derivatives with antitumor activity and synthesis method thereof

The technology of a licorice chalcone and a synthetic method, which is applied in the field of medicinal chemistry, can solve problems such as poor water solubility, and achieve the effects of low production cost, mild reaction conditions, and environmentally friendly raw materials

Inactive Publication Date: 2017-05-17
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology provides technical benefits such as environmentally friendly manufacturing processes with lower costs compared to previous methods or improved operating security during reactions. It also allows us to use reactants that are safe at all times without causing harm if they don't have any side-effects on their ownerself. Overall, it offers an effective way to make certain types of molecules from natural sources more efficiently while reducing its negative impact upon our healthcare systems.

Problems solved by technology

The technical problem addressed by this patented study is how to develop an efficient way for treating cancers caused by certain chemicals called Lithochloride (chemically related to ginger).

Method used

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  • Licochalcone A thiouracil derivatives with antitumor activity and synthesis method thereof
  • Licochalcone A thiouracil derivatives with antitumor activity and synthesis method thereof
  • Licochalcone A thiouracil derivatives with antitumor activity and synthesis method thereof

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preparation example Construction

[0021] A kind of synthetic method of licochalcone A thiouracil derivatives comprises the following steps:

[0022] (1) Add licochalcone A and thiourea compounds into the reactor at a molar ratio of 1:1~1:1.5, add toluene or DMF and mix evenly, and the solvent volume is less than 2 / 3 of the reactor volume, Add organic base catalyst triethylamine, stir on a magnetic stirrer, heat to 80°C~120°C, and reflux for 3~8 hours;

[0023] (2) During the reaction process, use thin-layer chromatography to track and monitor the progress of the reaction in time. After the raw materials are completely reacted, stop heating and remove the condensing device;

[0024] (3) Concentrate the solid-liquid mixture of the reaction system in step (2) under reduced pressure, separate and purify by column chromatography, and dry to obtain the target product.

[0025] The compound structural formula in some preferred embodiments of the present invention is as follows:

[0026]

[0027]

[0028]

Embodiment 1

[0030] 6-(4-Hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-4-(4-hydroxyphenyl)-1-methyl-5 , Preparation of 6-dihydropyrimidine-2(1H)-thione (1).

[0031] In reactor, add 200mg (1mmol) licochalcone A and 68.44mg (1.3mmol) 1-methylthiourea, add 50ml toluene and 5mLDMF as reaction solvent, add 0.5mL triethylamine as catalyst, electric heating mantle is heated to 100°C, magnetically stirred and refluxed for 3 hours. The reaction was tracked by thin-layer chromatography. After the reaction was completed, it was concentrated under reduced pressure, and column chromatography was used to obtain a brown powder (113 mg). The total yield was 46.57%.

[0032]

[0033] Brown yellow crystalline powder solid. 1 H NMR(400MHz,DMSO-d6,300K):d 7.85(2H,d,J=7.52Hz), 6.95(1H,s), 6.85(2H,d,J=7.52Hz), 6.41(1H,s) , 6.30(1H,q), 5.35(2H,s), 5.00-4.98(2H,m), 3.9(1H,t), 3.83(3H,s), 3.04(3H,s), 1.76-1.51(2H ,m), 1.69(6H,s). 13 C NMR(75MHz,DMSO-d6)δ(ppm): 182.2, 164.6, 160.8, 156.1, 155.0, 148.8...

Embodiment 2

[0035] 1-Benzyl-6-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-4-(4-hydroxyphenyl)-5 , Preparation of 6-dihydropyrimidine-2(1H)-thione (2).

[0036] In reactor, add 200mg (1mmol) licochalcone A and 127.73mg (1.3mmol) 1-benzylthiourea, add 50ml toluene and 5mLDMF as reaction solvent, add 0.5mL triethylamine as catalyst, electric heating mantle is heated to 100°C, magnetically stirred and refluxed for 5 hours. The reaction was tracked by thin-layer chromatography. After the reaction was completed, it was concentrated under reduced pressure, followed by column chromatography and dried to obtain a brown powder (124.72mg), with a total yield of 43.36%.

[0037]

[0038] Brown yellow crystalline powder solid. 1 H NMR(400MHz,DMSO-d6,300K):d 7.85(2H,d,J=7.52Hz), 7.33(2H,m),7.23(2H,m), 7.26(1H,m), 6.95(1H, s), 6.85(2H,d,J=7.52Hz),6.41(1H,s), 6.30(1H,q), 5.35(2H,s), 5.00-4.98(2H,m), 3.9(1H,t ), 3.83(3H,s),3.81(2H,s), 1.76-1.51(2H,m), 1.69 (6H,s). 13 C NMR(75MHz,DMSO-d6)...

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Abstract

The invention discloses licochalcone A thiouracil derivatives with antitumor activity and a synthesis method thereof. The licochalcone A thiouracil derivatives, compounds, are synthesized from licochalcone A and thiourea compounds by reacting with methylbenzene as a solvent. The synthesis method has the advantages of high safety and mild reaction conditions and is applicable to industrialized production. Preliminary biological activity tests show that the compounds are high in antitumor activity and can be used for studying antitumor lead compounds.

Description

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Claims

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Application Information

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Owner SHAANXI UNIV OF SCI & TECH
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