Flavanone derivatives, preparation method and use thereof

A technology for dihydroflavonoids and derivatives, which is applied in the field of dihydroflavonoid derivatives and their preparation, can solve the problems of inability to be widely used, difficult extraction of natural dihydroflavonoids, and difficulty in obtaining them.

Inactive Publication Date: 2009-12-16
李青山 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the problems that the existing natural dihydroflavonoid compounds are difficult to extract, difficult to obtain and unable to be widely used, the present invention provides a dihydroflavone derivative and its preparation method and use

Method used

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  • Flavanone derivatives, preparation method and use thereof
  • Flavanone derivatives, preparation method and use thereof
  • Flavanone derivatives, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation of Compound 1-a: (6' Hydroxy-5,7 Dihydroxy-6,8-Dimethyldihydroflavone):

[0055] Dissolve 200 mg (0.001mol) of 6-hydroxyl-2,4-hydroxy-3,5-dimethylacetophenone, 125 mg (0.001mol) of 2-hydroxybenzaldehyde, and 61 mg (0.001mol) of boric acid in a small amount of ethylene glycol In alcohol, heat up at 100°C, stir and react for 1 hour, dissolve the reactant with ethanol, and obtain 30 mg of a light green substance through column chromatography, with a yield of 15%, HNMR (500MHz, DMSO), δ7.02 (2H, d , J=8.4Hz, H-e), 6.75 (1H, d, J=8.5Hz, H-d), 6.65 (1H, d, J=8.5Hz, H-d), 5.58 (1H, dd, J=12.3, 2.7Hz, H-c), 3.18 (1H, dd, J=17.0, 12.5Hz, H-b 2 ), 2.86 (1H, dd, J=17.0, 3.0Hz, H-b 1 ), 1.97 (6H, d, J=4.5Hz, H-a) ESI-MS (m / z): [M-1] - =299.

Embodiment 2

[0056] Example 2: Preparation of Compound 1-b: (4' Chloro-5,7 Dihydroxy-6,8-Dimethyldihydroflavone):

[0057] Dissolve 200 mg (0.001mol) of 6-hydroxy-2,4-hydroxy-3,5-dimethylacetophenone, 700 mg (0.005mol) of 4-chlorobenzaldehyde, and 270 mg (0.005mol) of citric acid in a small amount of ethanol , the temperature was raised at 200°C, the reaction was stirred for 5 hours, the reactant was dissolved in ethanol, and 25 mg of a light green substance was obtained by column chromatography, with a yield of 12.5%, HNMR (500MHz, DMSO), δ7.56 (2H, d, J = 8.4Hz, H-e), 7.51 (2H, d, J = 8.5Hz, H-d), 5.58 (1H, dd, J = 12.3, 2.7Hz, H-c), 3.18 (1H, dd, J = 17.0, 12.5Hz , H-b2), 2.86 (1H, dd, J=17.0, 3.0Hz, H-b1), 1.97 (6H, d, J=4.5Hz, H-a) ESI-MS (m / z): [M-1 ]-=317.

Embodiment 3

[0058] Example 3: Compound 1-n: 2-(furan-2-yl)-5,7-dihydroxy-6,8-methyl-chroman-4-one

[0059] 200 mg (0.001mol) of 6-hydroxyl-2,4 hydroxy-3,5 dimethylacetophenone, 0.3ml (0.0015mol) of furfural, and 250 mg (0.004mol) of tartaric acid were dissolved in a small amount of glycerol, and the temperature was raised in 50 DEG C, stirred and reacted for 15 hours, the reactant was dissolved in ethanol, and 35 mg of a light yellow substance was obtained through column chromatography, with a yield of 15%.

[0060] HNMR (500MHz, DMSO) δ7.36 (H, d, J=8.4Hz, H-e), 6.26 (H, d, J=8.5Hz, H-d), 6.19 (H, d, J=8.5Hz, H-d), 5.74 (1H, dd, J=12.3, 2.7Hz, H-c), 3.18 (1H, dd, J=17.0, 12.5Hz, H-b 2 ), 2.85 (1H, dd, J=17.0, 3.0Hz, H-b 1 ), 1.99 (6H, d, J=4.5Hz, H-a) ESI-MS (m / z): [M-1] - =257.

[0061] The following compounds were synthesized according to the above preparation methods.

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Abstract

The invention relates to polyphenol substances, a synthesis method and use thereof, in particular to flavanone derivatives, a preparation method and use thereof, which solves the problem that the prior natural flavanone compounds are difficult to extract, not easy to obtain and incapable of extensive use. The compounds have a structure (as above), wherein R1, R2 and R3 are selected from hydrogen, 1 to 8 carbonic alkyl groups, halogen, nitro group, 1 to 8 carbonic alkoxy or amino groups respectively; R4 and R5 can be selected from 1 to 8 carbonic alkyl groups, 1 to 8 alkoxy or alkenyl groups respectively; and the compounds are obtained through the reaction of compound 6-hydroxy-2,4-hydroxy acetophenone substances and aromatic aldehydes or heterocyclic aldehyde substances in polyalcohol solvent by taking high-boiling-point acid as a catalyst, and can be applied to the preparation of medicaments for resisting tumors and cardiovascular and cerebrovascular diseases. The flavanone derivatives have the activity of resisting tumors and inhibiting the cardiovascular and cerebrovascular diseases, thereby opening up a new way for preparing the medicaments and bringing new breakthroughs for the medicament field. Moreover, the synthesis method has the advantages of mild conditions and easy operation.

Description

technical field [0001] The present invention relates to polyphenolic substance and its synthesis method and application, in particular to a dihydroflavonoid derivative and its preparation method and application. Background technique [0002] Dihydroflavonoids are a class of polyphenols widely distributed in nature. Dihydroflavonoids have a wide range of biological and pharmacological activities. A large number of studies have shown that dihydroflavonoids have the functions of scavenging free radicals, anti-oxidation, anti-mutation, anti-tumor, anti-bacterial, anti-virus, regulating immunity, preventing and curing vascular sclerosis, and lowering blood sugar. Some of them have been proved to have anti-HIV virus activity . However, flavonoids are a class of low-molecular-weight natural plant components widely distributed in the plant kingdom, and are metabolites of plant polyphenols. They are considered as a class of trace flavonoids because their distribution in nature is r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32C07D407/04A61K31/352A61P35/00A61P9/00
Inventor 李青山石磊韩玲革
Owner 李青山
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