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Hesperetin cinnamate compound with anti-tumor activity and synthetic method thereof

A technology of cinnamic esters with anti-tumor activity, applied in the field of medicinal chemistry, can solve problems such as treatment failure, and achieve the effects of low production cost, high operation safety, and full utilization of reaction raw materials

Inactive Publication Date: 2017-04-19
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mechanism of action of anti-tumor drugs and the targets of drugs are various, and the multi-drug resistance of tumor cells often leads to the failure of treatment.

Method used

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  • Hesperetin cinnamate compound with anti-tumor activity and synthetic method thereof
  • Hesperetin cinnamate compound with anti-tumor activity and synthetic method thereof
  • Hesperetin cinnamate compound with anti-tumor activity and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of compound (S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochroman-7-ylcinnamic acid (I-1);

[0037] 100 g of hesperidin and 45.4 g of potassium carbonate were dissolved in dimethylformamide at 10° C. and stirred at 90° C. for 6 hours. The reacted solution was cooled to room temperature. To the solution was added 100 g of iodomethane, followed by stirring at room temperature for 8 hours. After the reaction was completed, 5 L of a mixture of ethyl acetate and dichloromethane (3:2) was added thereto. The resulting solution was stirred for 2 hours, and the precipitated solid was collected by filtration and washed with a small amount of ethanol to obtain the target compound (yellow solid, 40.1 g, yield: 81.5%), whose structural formula is shown in formula (I-1).

[0038]

[0039] 1 H-NMR(300MHz,DMSO)δ:11.35(1H,m),7.60(2H,m),7.48(1H,s),7.40(2H,m),7.33(1H,m),6.99(1H,m ),6.81-6.75(2H,J=7.5,m),6.52-6.48(2H,m),6.31(1H,s),5.51(1H,s),5.35(1H,s),3.83(3H,s ),3....

Embodiment 2

[0041] Compound (S,E)-5-Hydroxy-2-(3-Hydroxy-4-methoxyphenyl)-4-oxochroman-7-yl 3-(p-tolyl)acrylate Preparation of (I-2).

[0042] 100 g of hesperidin and 45.4 g of potassium carbonate were dissolved in dimethylformamide at 10° C. and stirred at 90° C. for 6 hours. The reacted solution was cooled to room temperature. To the solution was added 100 g of iodomethane, followed by stirring at room temperature for 8 hours. After the reaction was completed, 5 L of a mixture of ethyl acetate and dichloromethane (3:2) was added thereto. Add aluminum chloride again, pass into chlorine gas, the obtained solution is stirred for 2 hours, and the precipitated solid is collected by filtration, and washed with a small amount of ethanol to obtain the target compound (light yellow solid, 41.1g, yield: 83.5%), its structural formula is as follows Formula (I-2) shown.

[0043]

[0044] 1 H-NMR(300MHz,DMSO)δ:11.35(1H,m),7.68(2H,m),7.48(1H,s),7.44(2H,m),6.99(1H,m),6.85-6.71(2H ,J=7.5,m),6.52...

Embodiment 3

[0047] Compound (S,E)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochroman-7-yl3-(4-chlorophenyl) Preparation of acrylate (I-3).

[0048] 100 g of hesperidin and 45.4 g of potassium carbonate were dissolved in dimethylformamide at 10° C. and stirred at 90° C. for 6 hours. The reacted solution was cooled to room temperature. To the solution was added 100 g of iodomethane, followed by stirring at room temperature for 8 hours. After completion of the reaction, add 5L of ethyl acetate and dichloromethane (3:2) mixed solution therein, add nitric acid and sulfuric acid mixture after stirring, filter and collect the precipitated solid after the solution was stirred for 2 hours, and wash with a small amount of ethanol, The target compound (white solid, 39.8 g, yield: 79.6%) was obtained, and its structural formula is shown in the following formula (I-3).

[0049]

[0050] 1 H-NMR(300MHz,DMSO)δ:11.35(1H,m),8.21(2H,m),8.03(2H,m),7.62(1H,s),6.99(1H,m),6.81-6.75(2H ,J=7.5,m),6.60(...

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Abstract

The invention provides a hesperetin cinnamate compound with anti-tumor activity and a synthetic method thereof. The hesperetin cinnamate compound with a novel structure is synthesized by using hesperidin and a derivative thereof, and cinnamate and a derivative thereof as raw materials through simple reactions like hydrolytic desugarization and esterification with DMF as a solvent. The method provided by the invention has the advantages of easily available raw materials, mild reaction conditions, and applicability to industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a hesperetin cinnamate compound with antitumor activity and a synthesis method thereof. Background technique [0002] Tumor is a disease that seriously threatens human health, and tumor is essentially a genetic disease. DNA damage induced by various environmental and genetic carcinogens in a concerted or sequential manner, resulting in the activation of proto-oncogenes and / or the inactivation of tumor suppressor genes, coupled with alterations in apoptosis-regulating genes and / or DNA repair genes , which in turn causes abnormal expression levels and transforms target cells. The transformed cells are mostly clonal proliferation, and after a long multi-stage evolution process, one of the clones expands relatively unrestricted, and selectively forms subclones with different characteristics (heterogeneity) through additional mutations. ), thereby gaining the ability to invade and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32A61P35/00
CPCC07D311/32C07B2200/07
Inventor 梁承远贾敏一田丹妮鞠伟会黄尊程关磊孙涵丁顺军
Owner SHAANXI UNIV OF SCI & TECH
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