Chlorogenic acid derivative capable of clearing away heat and toxic materials and preparation method thereof

A heat-clearing and detoxifying, chlorogenic acid technology, which is applied in the field of heat-clearing and detoxifying chlorogenic acid derivatives and its preparation, can solve the problems of difficult transdermal absorption, gastric mucosal irritation, unstable double bonds, etc., and achieve significant and significant inhibitory activity Inhibitory effect, good effect of inhibitory effect

Inactive Publication Date: 2021-05-28
谢天龙
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is a carboxyl group in the chlorogenic acid structure, which makes the medicine acidic, which can cause great irritation to the gastric mucosa when taking an acidic medicine orally, and cause irritation to the skin or difficult transdermal absorption when it is used externally; The presence of unstable double bonds affects the stability of the overall structure of chlorogenic acid, which ultimately leads to the inability to fully utilize the biological activity of chlorogenic acid

Method used

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  • Chlorogenic acid derivative capable of clearing away heat and toxic materials and preparation method thereof
  • Chlorogenic acid derivative capable of clearing away heat and toxic materials and preparation method thereof
  • Chlorogenic acid derivative capable of clearing away heat and toxic materials and preparation method thereof

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Embodiment 1

[0021] (1) Under the protection of nitrogen, dissolve 20 g of chlorogenic acid in 120 mL of methanol solution at room temperature, add 2 g of p-toluenesulfonic acid in batches, raise the temperature to 100 ° C, stir and reflux for 20 h, and TLC detects that the reaction is complete. Wash with saturated sodium bicarbonate solution and water successively, extract with ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain Compound A;

[0022] (2) Dissolve 15.6g of Compound A in 100mL of chloroform, add 5.1g of 2-amino-3-ethylpyridine, heat up to 80°C, react for 7h, TLC detects that the reaction is complete, let stand and cool to room temperature, and vacuum the filtrate Suction filtration and drying; then transfer the dried product to a reaction container, slowly add 8.4 g of thioacetic acid dropwise at room temperature, after the dropwise addition, react for 3 hours, and when the reaction ends, add saturated...

Embodiment 2

[0025] Embodiment 2 The compound of the present invention is to the pharmacodynamics test of heat-clearing and toxic substances removing

[0026] 1. In vitro antibacterial activity experiment of medicine of the present invention

[0027] Tested strains: Staphylococcus aureus (a), Staphylococcus epidermidis (b), Candida albicans (c), Pneumococcus pneumoniae (d), Pseudomonas aeruginosa (e), beta-hemolytic streptococcus (f).

[0028] Dissolve the chlorogenic acid derivative of the present invention in absolute ethanol, dilute to 1000 μg / mL with tryptone soybean broth culture solution, continue to dilute with culture solution to make the drug concentration 256-0.25 μg / mL, and obtain the experimental solution and Qingkailing injection with a concentration range of 256-0.25 μg / mL was prepared as a positive control group (control group 1); the same method was used to prepare chlorogenic acid as a control group 2. Add a drug solution with a concentration range of 256-0.25 μg / mL and 1...

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Abstract

The invention discloses a chlorogenic acid derivative capable of clearing away heat and toxic materials and a preparation method thereof, and belongs to the technical field of synthesis and preparation of chemical drugs. The preparation method of the derivative comprises the following steps: under the action of a catalyst, carrying out esterification on chlorogenic acid and methanol, then carrying out ester ammonolysis with 2-amino-3-ethylpyridine, carrying out double-bond addition with thioacetic acid, and purifying a crude product through a silica gel column to obtain the chlorogenic acid derivative. According to the invention, the structure of chlorogenic acid is modified, a compound with a more novel structure and stronger activity is found, and the compound has remarkable effects of clearing away heat and toxic materials, resisting bacteria and diminishing inflammation and the like; and the chlorogenic acid derivative prepared by the method disclosed by the invention is high in yield, simple in process, mild in reaction condition and good in yield and selectivity, and has economic characteristics of an industrial application environment.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis and preparation, and relates to a heat-clearing and detoxifying chlorogenic acid derivative and a preparation method thereof. Background technique [0002] Chlorogenic acid is a phenylpropanoid compound produced through the shikimic acid pathway in plants during aerobic respiration. It has been highly concerned by scholars since it was first successfully extracted from apples in the 1950s. Studies have shown that chlorogenic acid has the effect of clearing away heat and detoxifying, and is often used in traditional Chinese medicine preparations for clearing away heat and detoxifying. However, there is a carboxyl group in the chlorogenic acid structure, which makes the medicine acidic, which can cause great irritation to the gastric mucosa when taking an acidic medicine orally, and cause irritation to the skin or difficult transdermal absorption when it is used externally; The pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/75A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D213/75
Inventor 谢天龙
Owner 谢天龙
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