Antiviral andrographolide derivative and preparation method thereof

A technology of andrographolide and its derivatives, applied in antiviral agents, organic chemical methods, pharmaceutical formulations, etc., can solve the problems of low protein content, limited therapeutic effect of antiviral drugs, simple virus structure, etc., and achieve improved water solubility, The effect of improving bioavailability and simple preparation method

Pending Publication Date: 2021-01-29
谢天龙
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Judging from the antiviral drugs currently used or to be used clinically, although this type of western medicine is safe, due to the simple virus structure and low protein content, long-term use of such antiviral drugs will form strong drug resistance Sexuality, leading to the limitation of the therapeutic effect of antiviral drugs commonly used in clinic

Method used

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  • Antiviral andrographolide derivative and preparation method thereof
  • Antiviral andrographolide derivative and preparation method thereof
  • Antiviral andrographolide derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] In a 100mL single-necked bottle, add 20g of andrographolide, add 40mL of tetrahydrofuran under the protection of nitrogen, stir to dissolve, adjust the temperature to 5°C, add 6g of N,N'-carbonyldiimidazole in batches, reflux for 4~6h, TLC Detect that the reaction is complete, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, and the filtrate is subjected to silica gel under the eluent ratio of petroleum ether:ethyl acetate=2:1 by volume. Column chromatography, the obtained chromatographic solution was concentrated, and then extracted with ethyl acetate, the ethyl acetate extract was concentrated, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 79.34%.

Embodiment 2

[0022] In a 100mL single-necked bottle, add 20g of andrographolide, add 40mL of tetrahydrofuran under nitrogen protection, stir to dissolve, adjust the temperature to 7°C, add 6g of N,N'-carbonyldiimidazole in batches, reflux for 4~6h, TLC Detect that the reaction is complete, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, and the filtrate is subjected to silica gel under the eluent ratio of petroleum ether:ethyl acetate=2:1 by volume. Column chromatography, the obtained chromatographic liquid was concentrated, and then extracted with ethyl acetate, the ethyl acetate extract was concentrated, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 80.56%.

Embodiment 3

[0024] In a 100mL single-necked bottle, add 20g of andrographolide, add 40mL of tetrahydrofuran under the protection of nitrogen, stir to dissolve, adjust the temperature to 9°C, add 6g of N,N'-carbonyldiimidazole in batches, reflux for 4~6h, TLC Detect that the reaction is complete, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, and the filtrate is subjected to silica gel under the eluent ratio of petroleum ether:ethyl acetate=2:1 by volume. Column chromatography, the obtained chromatographic solution was concentrated, and then extracted with ethyl acetate, the ethyl acetate extract was concentrated, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 80.77%.

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PUM

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Abstract

The invention discloses an antiviral andrographolide derivative and a preparation method thereof, and the preparation method comprises the following steps: adding andrographolide and N, N '-carbonyldiimidazole into an organic solvent, obtaining a novel andrographolide derivative through a one-step method, and because an imidazole group is easy to dissolve in water, the solubility of the obtained compound is significantly improved, and the bioavailability of the compound is improved; pathological experiments show that the andrographolide derivative can obviously reduce pneumonia of virus mice,the treatment effect is equivalent to that of ribavirin, and the anti-pneumonia virus activity of the andrographolide derivative is even better than that of the andrographolide and the N, N '-carbonyldiimidazole monomer substances; and the preparation method provided by the invention is simple, easily available in raw materials, high in yield and mild in operation conditions, can be used for conveniently preparing the andrographolide derivative, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to an antiviral andrographolide derivative and a preparation method thereof. Background technique [0002] Viruses are the smallest of pathogenic microorganisms. They reproduce in cells. Their core is ribonucleic acid (RNA) or deoxyribonucleic acid (DNA). The outer shell is protein and does not have a cellular structure. At present, the main clinical method for treating viral infections is to use broad-spectrum antiviral drugs and immunomodulators, such as acyclovir, ribavirin, polyinosinic acid, and amantadine hydrochloride. Most antiviral drugs are viral polymerase inhibitors, which are mainly used to resist or destroy viral infection, such as directly inhibiting or killing viruses, interfering with virus adsorption, and enhancing host antiviral capabilities. Judging from the antiviral drugs currently used or to be used clinically, although this type of western medi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61K31/4178A61P31/12A61P31/16
CPCC07D405/12A61P31/12A61P31/16C07B2200/07
Inventor 谢天龙
Owner 谢天龙
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