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A kind of Usnea esterified derivative and its synthetic method

A technology of usnic acid ester and synthesis method, which is applied in the directions of organic chemistry, antibacterial drugs, etc., can solve the problems such as the synthesis method of usnic acid monoester derivatives that have not been found in research, and achieve the effect of high antibacterial properties.

Active Publication Date: 2022-02-08
TIANJIN UNIV OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no research to discover the synthetic method of usnic acid monoester derivatives

Method used

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  • A kind of Usnea esterified derivative and its synthetic method
  • A kind of Usnea esterified derivative and its synthetic method
  • A kind of Usnea esterified derivative and its synthetic method

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preparation example Construction

[0052] The present invention also provides a method for synthesizing the usnea esterified derivatives. Synthesizing the above-mentioned usnea esterified derivatives specifically includes the following steps:

[0053] Step 1: Put usnic acid in distilled water, stir in an ice-water bath, add dropwise an alkali solution, usually NaOH solution, until the usnic acid dissolves;

[0054] Wherein, the mass volume ratio of the usnic acid to the distilled water is 30~800mg / ml;

[0055] Step 2: Continue to stir for 10-100 minutes, add the corresponding acid chloride organic solution, and keep the reaction under ice-water bath conditions until the reaction equilibrium is reached;

[0056] Wherein, the mol ratio of usnic acid and acid chloride is 1:5~1:7, preferably 1:6, adopts thin-layer chromatography to monitor whether to reach reaction balance;

[0057] Step 3: Use an organic solvent to extract to neutrality, dry, and recover the solvent under reduced pressure to obtain a crude produc...

Embodiment 1

[0059] Weigh 500 mg of usnic acid into a reaction flask, add 2-3 ml of distilled water, stir in an ice-water bath, and add a few drops of 0.1-0.3 g / ml NaOH solution. Stirring was continued for 10-20min, anhydrous acetone dilution of phenylacetyl chloride (1.54ml) was added, and the reaction was maintained in an ice-water bath for 30-80min, and the reaction progress was monitored by thin-layer chromatography until the reaction reached equilibrium. Extracted with dichloromethane to neutrality, dried over anhydrous sodium sulfate, and recovered the solvent under reduced pressure to obtain a crude product, which was separated by silica gel column chromatography to obtain 404 mg of the product (compound 1), a yellow oil, the yield was 60.1%, and the structure was

[0060]

[0061] Proton NMR spectrum analysis: 1 H NMR (CDCl 3 ,600MHz)δ:1.79(s,3H),1.90(s,3H),2.56(s,3H),2.66(s,3H),3.95(s,2H),5.97(s,1H),7.29-7.31 (m,1H),7.35-7.38(m,2H),7.40-7.41(m,2H),11.05(s,1H),18.85(s,1H). fi...

Embodiment 2

[0064] Weigh 500 mg of usnic acid into a reaction flask, add 2-3 ml of distilled water, stir in an ice-water bath, and add a few drops of 0.1-0.3 g / ml NaOH solution. Continue to stir for 10-20min, add p-chlorobenzoyl chloride (1.48ml) anhydrous acetone diluent, keep the reaction in an ice-water bath for 30-80min, and monitor the reaction progress by thin-layer chromatography until the reaction reaches equilibrium. Extracted with dichloromethane to neutrality, dried over anhydrous sodium sulfate, recovered the solvent under reduced pressure to obtain a crude product, separated by silica gel column chromatography, and further separated by Sephadex column to obtain 387.6 mg of the product (compound 2). rate 55.3%, the structure is

[0065]

[0066] Proton NMR spectrum analysis: 1 H NMR (CDCl 3 ,600MHz)δ:1.84(s,3H),2.10(s,3H),2.56(s,3H),2.68(s,3H),6.00(s,1H),7.50(d,J=8.58Hz,2H ), 8.13(d, J=8.52Hz, 2H), 11.14(s, 1H), 18.87(s, 1H). Such as image 3 shown

[0067] Carbon NMR ...

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Abstract

The invention discloses a class of usnea esterified derivatives, which have higher antibacterial properties. The invention also discloses a synthesis method of usnea esterified derivatives. Usnea acid, different aromatic acid chlorides, and different branched chain acid chlorides are used as raw materials, and usnea acid can be synthesized by esterification using the phenolic hydroxyl properties of usnea acid. Acid monoester derivatives with higher antibacterial properties.

Description

technical field [0001] The invention relates to the technical field of synthesis of usnea esterified derivatives, more specifically, the present invention relates to a kind of usnea esterified derivatives and a synthesis method thereof. Background technique [0002] The emergence of antibiotics has made great contributions to the treatment of infectious diseases and human health. In recent years, with the widespread clinical application of antibiotics, synthetic and semi-synthetic antibacterial drugs, many serious infectious diseases have been effectively controlled. However, due to the abuse of antibiotics, the phenomenon of bacterial resistance to antibiotics is becoming more and more serious, and the continuous increase and spread of drug-resistant bacteria have caused serious harm to human health. The problem of drug resistance has become a major challenge in the field of global public health: the evolution and spread of drug-resistant bacteria are amazing, causing seri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/91A61P31/04
CPCC07D307/91A61P31/04
Inventor 王莉宁贾妍赵启铎牟佳佳葛军邓雁如任晓亮王丽莉
Owner TIANJIN UNIV OF TRADITIONAL CHINESE MEDICINE
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