Derivatives of flavonoids compounds and preparation method and application thereof

A technology of flavonoids and derivatives, applied in medical preparations containing active ingredients, organic chemistry, drug combinations, etc., can solve the problems of urgent research, strong side effects and drug resistance, and achieve good tumor activity and tumor inhibition activity , the effect of easy access to raw materials

Inactive Publication Date: 2012-07-18
SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cancer is a malignant tumor. Cancer has seriously threatened human health and life. The combination of traditional chemotherapy drugs, surgery, and radiotherapy has successfully improved the cure rate of various malignant tumors. However, due to strong side effects and resistance Drug properties, making it urgent to find new drugs

Method used

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  • Derivatives of flavonoids compounds and preparation method and application thereof
  • Derivatives of flavonoids compounds and preparation method and application thereof
  • Derivatives of flavonoids compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1. Preparation of 3', 5'-dimethoxy-6-chloroflavone

[0033] Step 1): Add 50ml of ice water, 10mmol of p-chlorophenol, and 15mmol of sodium hydroxide into a 100mL flask, slowly add 15mmol of acetic anhydride under stirring conditions, continue to stir at room temperature for 2.5h, stop the reaction, use ethyl acetate to extract three times, anhydrous Dried over magnesium sulfate and rotary steamed under pressure to obtain the desired compound -4-chlorophenol acetate.

[0034] Step 2): Add 5mmol acetic acid-4-chlorophenol ester, 7.5mmol anhydrous aluminum chloride, 7.5mmol sodium chloride into a 100ml beaker and react for 2h under melting and stirring, then add ice water, extract, dry, and rotary steam under reduced pressure to obtain Rearranged 2-acetyl-4-chlorophenol.

[0035] Step 3): Add 5ml of anhydrous pyridine and 1.5mmol of 3,5-dimethoxybenzoyl chloride into a 100ml flask, add 1mmol of 2-acetyl-4 chlorophenol under stirring conditions, continue to reac...

Embodiment 2

[0038] Embodiment 2, preparation compound 2'-chloro-4'-nitro-6-isopropylflavone

[0039] Step 1): Add 50ml of ice water, 10mmol of p-isopropylphenol, and 15mmol of sodium hydroxide into a 100mL flask, slowly add 15mmol of acetic anhydride under stirring conditions, continue to stir at room temperature for 2.5h, stop the reaction, and extract it roughly three times with ethyl acetate, Dry over anhydrous magnesium sulfate, and pressurize and rotary evaporate to obtain the desired compound -4-isopropylphenol acetate.

[0040] Step 2): Add 5mmol acetic acid-4-isopropylphenol ester, 7.5mmol anhydrous aluminum chloride, 7.5mmol sodium chloride into a 100ml beaker and react for 2h under melting and stirring, then add ice water, extract, dry, spin under reduced pressure Evaporation affords the rearranged 2-acetyl-4-isopropylphenol.

[0041] Step 3): Add 5ml of anhydrous pyridine and 1.5mmol of 2-chloro-4-nitrobenzoyl chloride into a 100ml flask, add 1mmol of 2-acetyl-4 isopropylpheno...

Embodiment 3

[0044] Embodiment 3, preparation 2'-chloro-4'-amino-6-isopropylflavone

[0045] Add 0.5mmol of 2'-chloro-4'-nitro-6-isopropylflavone prepared in Example 2 to a 50ml round low flask, then add 15ml of glacial acetic acid, stir under ice bath, add 2mmol of zinc powder, 0.5h After the reaction was complete, the unreacted zinc powder was filtered out, and the glacial acetic acid was removed under reduced pressure. The residue is separated by column chromatography, and the silica gel column used is purchased from Beijing Xinweier Glass Instrument Co., Ltd. The chromatographic column model is C384630C, and the length and internal diameter ratio is 305mm: 40mm. When used to separate the product of the present invention, the eluent used is Ethyl acetate (V): Petroleum ether (V)) = 1:5 ~ 1:10 mixed solution, the eluent flows under normal pressure (2ml / min), detects the effluent according to TLC thin layer chromatography, and depressurizes The product obtained by rotary evaporation is w...

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Abstract

The invention discloses derivatives of flavonoids compounds and a preparation method and application thereof. The general formula of the compounds is shown in the formula I in the specification. The preparation method provided by the invention is characterized in that corresponding phenol 1 (such as p-chlorophenol, alpha-naphthol and the like) is stirred in iced water solution with the ratio of phenol to acetic oxide to sodium hydroxide being 1:2-3:2-3 to obtain acetylate; anhydrous aluminium chloride and sodium chloride are melted and stirred for 2h to obtain corresponding rearranged phenol;the rearranged phenol reacts with different acyl chloride in the presence of pyridine to obtain substituted phenylethyl benzoate; the substituted phenylethyl benzoate is heated by anhydrous pyridine and potassium hydroxide to obtain corresponding different substituted dibenzoylmethane; and the different substituted dibenzoylmethane flows back and is stirred in glacial acetic acid and concentratedsulfuric acid to obtain the structural formula I. The compounds have good anti-tumor effect and have important practical value and application prospect in the field of preparing anti-tumor drugs.

Description

technical field [0001] The invention relates to derivatives of flavonoids and their preparation methods and applications. Background technique [0002] Flavonoids are a class of polyphenolic compounds that widely exist in plants in nature, not only in large quantities, but also in complex and diverse structures. Flavonoids have many important physiological and biochemical effects on mammalian and other types of cells due to their unique chemical structures. On the one hand, flavonoids have high chemical reactivity, for example, they can scavenge free radicals in the body and have anti-oxidation effects; on the other hand, flavonoids have many important pharmacological effects, which can inhibit enzyme activity, resist Cancer, antibacterial, antiviral, anti-inflammatory, anti-allergic, anti-diabetic complications, etc., and non-toxic and harmless, it is of great significance to the treatment and prevention of degenerative diseases such as human tumors, aging, and cardiovascu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30C07D311/92A61K31/352A61P35/00A61P39/06A61P29/00A61P31/12A61P9/00A61P37/02
Inventor 蒋宇扬刘华臣董爱君
Owner SHENZHEN GRADUATE SCHOOL TSINGHUA UNIV
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