Andrographolide derivative for resisting influenza virus infection and preparation method thereof

A technology of andrographolide, anti-influenza virus, applied in the direction of antiviral agent, organic chemistry, etc., can solve the problems of high energy consumption, reduced synthesis yield, unfavorable amplification of production, etc., achieves broad application prospects, reduces the degree of disease, and survives. rate increase effect

Inactive Publication Date: 2021-07-27
籍建亚
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, people have also done a lot of research on the antiviral activity of andrographolide. For example, patent CN103739576B discloses a kind of antiviral andrographolide trisuccinate half ester glycine; Lactone derivatives, but the reaction lines of the above two preparation methods are too long in the preparation process, which reduces the overall synthesis yield and consumes a lot of energy, which is not conducive to large-scale production

Method used

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  • Andrographolide derivative for resisting influenza virus infection and preparation method thereof
  • Andrographolide derivative for resisting influenza virus infection and preparation method thereof
  • Andrographolide derivative for resisting influenza virus infection and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) 20g of andrographolide was dissolved in 100mL of dichloromethane, 16.3g of p-toluenesulfonyl chloride was added, 12g of pyridine was added, reacted for 12h under ice-bath conditions, quenched with absolute ethanol, and the remaining solvent, and the residue was washed with water and saturated brine in sequence, dried over anhydrous sodium sulfate, concentrated and crystallized to obtain compound 1;

[0025] (2) Dissolve 15g of Compound 1 in 100mL of dichloromethane, add 4.6g of caffeic acid, heat to 120°C, and reflux for 4h. Sodium hydrogen solution, water washing, anhydrous calcium chloride drying, the dried crude product was dissolved in chloroform, then mixed with 200-300 mesh silica gel, the sample was separated by silica gel column chromatography (eluent: V 甲醇 :V 氯仿 =10:1), the eluate was collected, concentrated and dried to obtain andrographolide derivatives with a yield of 55.29%.

Embodiment 2

[0026] Embodiment 2 drug effect test research of compound of the present invention

[0027] (1) Effects of compounds of the present invention on lung pathological changes in mice infected with H1N1 influenza virus

[0028] Choose some of the mice of Kunming grade, group randomly, be respectively normal control group (control group 1), virus control group (control group 2), Tamiflu control group (control group 3), experimental group (embodiment 1 is the test group). drug). Mice were lightly anesthetized with ether, and infected with 15 LD50 virus drops, 0.5 mL per mouse. The mice in each group began to be administered 24 hours after the virus infection, and the administration was continued for 7 days, once a day, and each time 10mL / kg was administered. Normal control group and virus control group were given equal volume of normal saline. After the last administration, the mice were deprived of food and water for 4 hours and then dissected. The weight of the mice was weighed...

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Abstract

The invention provides an anti-influenza virus andrographolide derivative and a preparation method thereof. The preparation method comprises the following steps: dissolving andrographolide in an organic solvent, and conducting esterifying with caffeic acid to obtain the andrographolide derivative with a novel structure. The novel compound, namely the andrographolide derivative can reduce the lung index of influenza virus-infected mice, and has an inhibition effect on influenza viruses; and with the novel compound, the lesion degrees of the lungs of the mice with influenza can be reduced, the lungs of the mice with influenza are obviously protected, and the survival rate of the mice is increased. The preparation method of the andrographolide derivative is simple, reaction conditions are easy to control, reproducibility is good, the utilization rate of raw materials is high, and the 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 derivative against influenza virus infection and a preparation method thereof. Background technique [0002] Andrographolide is the extract of Andrographis paniculata, a kind of bicyclic diterpene lactone, which is the main bioactive component of Andrographis paniculata. Dysentery has a special curative effect and is known as a natural antibiotic drug. In recent years, people have also done a lot of research on the antiviral activity of andrographolide. For example, patent CN103739576B discloses a kind of antiviral andrographolide trisuccinate half ester glycine; Lactone derivatives, but the reaction lines in the preparation process of the above two preparation methods are too long, which reduces the overall synthesis yield and consumes a lot of energy, which is not conducive to scale-up production. Contents of the invention [0003] In view o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58A61P31/16
CPCC07D307/58A61P31/16
Inventor 籍建亚
Owner 籍建亚
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