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Method for preparing caffeic acid hydroxycoumarin ester compounds

A technology of ester compound and hydroxycoumarin, which is applied in the formation/introduction of carboxylate groups, skin care preparations, cosmetics, etc., can solve the problems of cumbersome operation, high cost, and influence on caffeic acid ester, and achieve shortening Effects of reaction time, simplified operation, and reduced reaction cost

Inactive Publication Date: 2011-11-09
天津医学高等专科学校
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AI Technical Summary

Problems solved by technology

This two-step method is not only cumbersome to operate and takes a long time, but also some protective groups are expensive, and hydrolysis or catalytic reactions may affect the opening of the double bond of caffeic acid ester or the disconnection of the ester bond, resulting in the generation of too many by-products. Difficult separation, low yield and high cost

Method used

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  • Method for preparing caffeic acid hydroxycoumarin ester compounds
  • Method for preparing caffeic acid hydroxycoumarin ester compounds
  • Method for preparing caffeic acid hydroxycoumarin ester compounds

Examples

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Embodiment 1

[0030] Preparation of E-3-(3,4-dihydroxyphenyl)-2-acrylic acid-4-methylumbelliferone ester

[0031] (1) Add 0.5 g (3 mmol) of caffeic acid into a three-neck flask, add 10 ml of thionyl chloride to reflux for 2 hours, extract the thionyl chloride under reduced pressure, dissolve the residue in 5 ml of xylene, and transfer it to the dropping funnel spare.

[0032] (2) Grind 1.1g (6mmol) of 4-methylumbelliferone in a pulverizer, suspend in 4ml xylene, and pass into N 2 Gas, heated to boiling (reaction temperature is about 137 ~ 140 ° C), dropwise added the solution obtained in the above (1) step under stirring, controlled the rate of addition, slowly added dropwise, the dropwise addition was completed in about 1h40min, and continued to react for 15-20min (A total of about 2 hours of reaction), the reaction was stopped, cooled, filtered, washed with ether, washed with water, dried, and recrystallized with ethanol to obtain 0.65 g of light yellow flaky crystals, yield: 69.2%, mp22...

Embodiment 2

[0034] Preparation of E-3-(3,4-dihydroxyphenyl)-2-acrylic umbelliferyl ester

[0035] The preparation method and conditions are the same as in Example 1.

[0036] Raw material charging ratio: caffeic acid 0.5g (3mmol), thionyl chloride 10ml, umbelliferone 1g (6mmol), xylene consumption is the same as Example 1, recrystallizes with ethanol to obtain light yellow needle crystal 0.62g, yield: 68.9%, mp 227.8°C (Dec). Elemental analysis, found value (calculated value), %: C 66.79 (66.67), H 3.81 (3.73). 1 HNMR (DMSO-d6), δ: 6.45~6.47 (d, 1H, pyran-=CHCO), 6.49~6.52 (d, 1H, =CHCO), 6.79~7.34 (m, 5H, Ph), 7.70~7.73 (d, 1H, pyran-Ph CH=), 7.76~7.78(d, 1H, ph), 8.06~8.08(d, 1H, Ph-CH=), 9.28(S, 1H, OH), 9.72(S , 1H, OH).

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Abstract

The invention discloses a method for preparing caffeic acid hydroxycoumarin ester compounds. The compounds have a structure shown as a formula (I); and in the formula, R1 refers to hydrogen, alkoxy with 1 to 6 carbon atoms, hydroxyl, halogen or alkyl with 1 to 6 carbon atoms; R2 refers to hydrogen, alkoxy with 1 to 6 carbon atoms, hydroxyl or halogen; and R3 refers to hydrogen or methyl. The preparation method comprises the following steps of: preparing caffeic acid compounds into corresponding acyl chloride, and directly performing condensation reaction on the acyl chloride and hydroxycoumarin compounds at a reaction temperature suitable for a reactive solvent to reflux without protecting phenolic hydroxyl groups of the caffeic acid compounds. By the method, the operation is simplified, the reaction time is shortened, the reaction cost is reduced and high yield is achieved. The compounds have important application value for developing new medicines, and can serve as ultraviolet (UV) filtering agents in cosmetic preparations and intermediates in the medicine, pesticide and perfume industries.

Description

【Technical field】: [0001] The invention relates to a method for preparing caffeic acid hydroxycoumarin esters by reacting caffeic acid compounds with hydroxycoumarin compounds, in particular, the phenolic hydroxyl groups of caffeic acid compounds are directly combined with hydroxycoumarin without protection. An improved method for obtaining target compounds through condensation reactions of elemental compounds. 【Background technique】: [0002] It has been reported in the literature that caffeic acid phenylethyl alcohol, as the main active ingredient in the anti-tumor effect of propolis, has the ability to selectively kill tumor cells and significantly inhibit their growth. Significant inhibition of proliferation and induction of apoptosis. In addition, it is reported that coumarin compounds can not only directly inhibit cancer cells (such as kidney cancer, lung cancer, colon cancer, prostate cancer and leukemia, etc.), but also produce anti-cancer effects by enhancing the i...

Claims

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Application Information

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IPC IPC(8): C07D311/18C07D311/16C07B41/12A61P35/00A61Q17/04
Inventor 刘斌解红武马菁菁郭雪红
Owner 天津医学高等专科学校
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