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Caffeate derivative and preparation method thereof

A technology of caffeic acid and its derivatives, which is applied in the field of medicine, can solve the problems that affect the clinical application of caffeic acid, it is not easy to absorb and utilize, and the polarity of caffeic acid is high, and achieve excellent bioavailability, stable yield, and good biological activity. Effect

Inactive Publication Date: 2018-06-08
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Caffeic acid is highly polar, and its absolute bioavailability is low after gavage, making it difficult to be absorbed and utilized by the body. This problem limits and affects the clinical application of caffeic acid

Method used

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  • Caffeate derivative and preparation method thereof
  • Caffeate derivative and preparation method thereof
  • Caffeate derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052]

[0053] Reagent

[0054] Methanol analytically pure Nanjing Fuyu Fine Chemical Factory

[0055] Ethanol analytically pure Zhengzhou Damao Chemical Reagent Factory

[0056] Ethyl acetate Analytical grade Zhengzhou Damao Chemical Reagent Factory

[0057] Dichloromethane Analytical grade Tianjin Keyuan Industry & Trade Co., Ltd.

[0058] Chloroform Analytical Pure Nanjing Fuyu Fine Chemical Factory

[0059] Formic acid Analytical grade Tianjin Keyuan Industry & Trade Co., Ltd.

[0060] Dimethylformamide (DMF) Analytical grade Nanjing Fine Chemical Factory

[0061] Preparation of caffeic acid oleyl ester

[0062] Thin layer development conditions

[0063] The choice of developer: chloroform: methanol: formic acid = 9: 1: 0.5

[0064] The reaction chemical equation is as follows:

[0065]

[0066] 1. Take an analytical balance and weigh 0.0738g (0.0041mol) of caffeic acid raw material.

[0067] 2. Add the caffeic acid raw material into 3ml of anhydrous DMF, s...

Embodiment 2

[0081] Instrument, reagent are with embodiment 1.

[0082] Reaction formula:

[0083]

[0084] 1. Take an analytical balance and weigh 0.0738g (0.0041mol) of caffeic acid raw material. Add 3ml of anhydrous DMF, stir to make it completely dissolved.

[0085] 2. After stirring and adding 0.031 g (0.0022 mol) of potassium carbonate under ice bath conditions, stir in ice bath for two hours.

[0086] 3. Add 0.006g (0.0001mol) potassium iodide to the reaction solution under stirring in an ice bath, and then dropwise add 1 drop (about 0.033ml) 4-chloromethyl-5-methyl-2-oxo-1,3- After adding dioxole, the mixture was stirred in an oil bath.

[0087] 4. The mixture is gradually warmed up to 35°C within 1 hour, and stirred at 30-35°C for 2-3 hours. After the result of spotting the plate confirms that the reaction has been completed, the reaction is terminated.

[0088] 5. Slowly pour the above reaction solution into 10 ml of ice water with stirring.

[0089] 8. If there is no ob...

Embodiment 3

[0097] Three times of increasing dose experiments were carried out successively, and the mass of caffeic acid taken was: 0.738g; 7.38g; 21.56g (that is, magnified by ten times; one hundred times; three hundred times), and other reactions were added according to the ratio mentioned above. A total of about 29g of caffeic acid raw materials were put into the experiment.

[0098] product yield

[0099] CF-1:

[0100] Put in 29g of caffeic acid raw material, react through the above steps and then separate and purify by column chromatography, the quality of the obtained CF-1 is 10.2g, and the calculated yield is 35.2%.

[0101] CF-2:

[0102] Put in 29g of caffeic acid raw material, react through the above steps and separate and purify by column chromatography, the quality of the obtained CF-2 is 16.6g, and the calculated yield is 57.3%.

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Abstract

The invention belongs to the technical field of medicines, and particularly relates to a heterocyclopentene caffeate derivative and a preparation method thereof. Structural modification is performed on coffee acid as a raw material, a phenolic hydroxyl group and a carboxyl group therein are esterified, and through control of the reaction temperature and the using amount of a reactant, two types ofbrand-new heterocyclopentene caffeate CF-1 and CF-2 are synthesized respectively, which show relatively excellent biological activity and relatively high medicinal values.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a caffeic acid oleyl derivative and a preparation method thereof. Background technique [0002] Caffeic acid (CA) is a class of naturally occurring phenolic acid compounds, chemical name: 3-(3,4-dihydroxyphenyl)-2-acrylic acid, another name: 3,4-dihydroxycinnamic acid, chemical formula :C 9 h 8 o 4 , Molecular weight: 180.15, CAS number: 331-39-5, light yellow crystalline powder, not easily soluble in cold water, soluble in hot water and ethanol. There are unsaturated double bonds in its chemical structure, and it has some chemical properties of phenolic acid. Caffeic acid is widely distributed in various plants in different regions, and it exists in large quantities in the whole plant of a yellow flower (compositae plant), the root of valerian root (patinaceae plant), capillary chen (compositae plant), Shanlihong ( Rosaceae), the leaves of cardoon (Asteraceae),...

Claims

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Application Information

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IPC IPC(8): C07D317/40
CPCC07D317/40
Inventor 孙敬勇熊山孙捷孙皓熠王景璟方桂迁张浩超
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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