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Andrographolide gallate compound with antioxidant activity and preparation method of compound

A technology of andrographolide and antioxidant activity, which is applied in the fields of organic chemistry methods, anti-toxic agents, organic chemistry, etc., can solve the problems of andrographolide derivatives' stability decline and influence on pharmacological activity, and achieve significant antioxidant activity and structure Novel, high reaction efficiency effect

Inactive Publication Date: 2021-08-06
张洪胜
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Related documents are also reported. For example, patent CN103432118 discloses an andrographolide derivative combined with lipoic acid and andrographolide. This derivative has good activity in antioxidant properties, but lipoic acid (LA) is Unstable in the body, it will be converted into the reduced form of dehydrolipoic acid (DHLA), which will reduce the stability of lipoic acid-andrographolide derivatives and affect their pharmacological activity

Method used

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  • Andrographolide gallate compound with antioxidant activity and preparation method of compound
  • Andrographolide gallate compound with antioxidant activity and preparation method of compound
  • Andrographolide gallate compound with antioxidant activity and preparation method of compound

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Embodiment 1

[0030] (1) Weigh 15.0g of gallic acid and add it to 225mL of anhydrous carbon tetrachloride, reflux and dissolve for 30min, add 2~3 drops of N,N-dimethylformamide, and slowly add it at a temperature of -5~0℃ 78.2g of oxalyl chloride, raise the temperature to 80°C, reflux for 5h, the reaction is completed, and the excess oxalyl chloride can be removed by rotary evaporation;

[0031] (2) Weigh 10.0g of andrographolide in 100mL of anhydrous tetrahydrofuran, reflux and dissolve for 30min, add 18.4g of the product of step (1), then add 2 to 3 drops of N,N-dimethylformamide, and stir the reaction at room temperature After 5 hours, the reaction was completed, the solvent was concentrated under reduced pressure at 50°C, and dried over anhydrous sodium sulfate;

[0032] (3) Weigh 9.3g of the product of step (2) and dissolve it in 100mL of chloroform, add 5.6g of hydrofluoric acid, stir and react at room temperature for 7h, thin-layer chromatography shows no progress in the reaction, an...

experiment example 2

[0033] Experimental Example 2 Compounds of the present invention are tested for DPPH free radical scavenging ability

[0034] (1) Preparation of sample solution: Accurately weigh 4.7 mg of DPPH sample, dissolve it with absolute ethanol and dilute it to a 50 mL volumetric flask to obtain a DPPH solution with a concentration of 0.094 mg / mL. The andrographolide gallate compound was prepared into a 10mg / mL mother solution with absolute ethanol, stored at 4°C for later use, and the mother solution was diluted with absolute ethanol to a concentration of 1.20, 3.60, 14.4, 28.8, 12.0, 36.0, 144, 288 ( ppm) sample solution (experimental group) for scavenging DPPH free radical ability test.

[0035] Vitamin C sample solution (control group 1), andrographolide sample solution (control group 2), and gallic acid sample solution (control group 3) were prepared in the same way.

[0036] (2) Detection method: draw 0.1mL of sample solution and 0.1mL of DPPH solution into a test tube, mix well...

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Abstract

The invention provides an andrographolide gallate compound with antioxidant activity and a preparation method of the compound, and the preparation method comprises the following steps: dissolving gallic acid in an organic solvent, acylating, esterifying with andrographolide, and finally reacting with haloid acid to obtain an andrographolide derivative with a novel structure. The new compound has obvious scavenging capacity on DPPH free radicals, and the scavenging capacity is close to the scavenging capacity of vitamin C with the same concentration. The preparation method provided by the invention is simple, the raw materials are easy to obtain, the yield is high, the operation condition is mild, the andrographolide derivative can be conveniently prepared, and the preparation method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to an andrographolide gallate compound with antioxidant activity and a preparation method thereof. Background technique [0002] Andrographolide is an active ingredient of the natural plant Andrographis paniculata, which has the effects of clearing heat, detoxifying, reducing inflammation and relieving pain. Recent studies have shown that the antioxidant effect of andrographolide is mainly manifested in increasing SOD (superoxide dismutase), removing active oxygen, etc. Free radicals, slowing down pathological lipid peroxidation, anti-lipid peroxidation damage, etc. Related documents are also reported. For example, patent CN103432118 discloses an andrographolide derivative combined with lipoic acid and andrographolide. This derivative has good activity in antioxidant properties, but lipoic acid (LA) is Unstable in the body, it will be converted into the reduced form o...

Claims

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Application Information

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IPC IPC(8): C07D307/33A61P39/06
CPCC07D307/33A61P39/06C07B2200/07
Inventor 张洪胜
Owner 张洪胜