Antiviral ursolic acid derivative and preparation method thereof

A technology of viral ursolic acid and derivatives, applied in the directions of antiviral agents, steroids, organic chemistry, etc., can solve the problems of decreased yield of main products, unsuitable industrialization development, difficulty in solvent recovery, etc., and achieves improved solubility, Improved bioavailability, environmentally friendly effect

Inactive Publication Date: 2021-01-22
籍建亚
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned compounds are all formed by glycosidation. In the glycosylation reaction, the equivalent of the glycosyl donor needs a lot. When the glycosidic bond is formed, most of the by-products are disaccharide compounds, which are difficult to separate and reduce the yield of the main product; the above reaction The steps are too cumbersome and complicated, and it is inevitable that a large amount of organic solvents will be used as the reaction medium, resulting in difficulties in solvent recovery and a large waste of resources, resulting in hidden safety hazards, which are not suitable for industrial development

Method used

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  • Antiviral ursolic acid derivative and preparation method thereof
  • Antiviral ursolic acid derivative and preparation method thereof
  • Antiviral ursolic acid derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Weigh 20g of ursolic acid, add it into a 100mL round-bottomed flask, add 50mL of pyridine, stir well to dissolve, add 4g of N,N'-carbonyldiimidazole in batches, reflux at a temperature of 8-10°C for 4-6h, and detect by TLC After the reaction is completed, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, add 300-400 mesh silica gel to the filtrate, mix and dry, and elute by silica gel column chromatography (elution Agent: petroleum ether / ethyl acetate=3:1), the eluent was collected and concentrated, the concentrated solution was extracted with ethyl acetate, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 77.43%.

Embodiment 2

[0020] Weigh 20g of ursolic acid, add it to a 100mL round-bottomed flask, add 50mL of pyridine, stir well to dissolve, add 6g of N,N'-carbonyldiimidazole in batches, reflux at a temperature of 8-10°C for 4-6 hours, and detect by TLC After the reaction is completed, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, add 300-400 mesh silica gel to the filtrate, mix and dry, and elute by silica gel column chromatography (elution Agent: petroleum ether / ethyl acetate=3:1) The eluate was collected and concentrated, and the concentrated solution was extracted with ethyl acetate, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 78.69%.

Embodiment 3

[0022] Weigh 20g of ursolic acid, add it to a 100mL round-bottomed flask, add 50mL of pyridine, fully stir to dissolve, add 8g of N,N'-carbonyldiimidazole in batches, reflux at a temperature of 8-10°C for 4-6h, and detect by TLC After the reaction is completed, stop the reaction, concentrate under reduced pressure at 60°C to recover the solvent, then add absolute ethanol, stir to dissolve, filter, add 300-400 mesh silica gel to the filtrate, mix and dry, and elute by silica gel column chromatography (elution Agent: petroleum ether / ethyl acetate=3:1), the eluate was collected and concentrated, and the concentrated solution was extracted with ethyl acetate, crystallized, filtered, and vacuum-dried to obtain the target product with a yield of 79.49%.

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Abstract

The invention discloses an antiviral ursolic acid derivative and a preparation method thereof. The preparation method includes the steps that ursolic acid and N,N'-carbonyldiimidazole are added into an organic solvent, a novel ursolic acid derivative is obtained through a one-step reaction, and the solubility of a new compound is improved through an introduced imidazole structure. Pathological experiments show that the compound can remarkably reduce pneumonia of virus mice, and the treatment effect of the compound is equivalent to or even better than that of daphenanthrene and ribavirin. The preparation method provided by the invention is simple, easily available in raw materials, mild in operation conditions, recyclable in solvent and environment-friendly, and subsequent main products andbyproducts can be thoroughly separated, so that the yield of the main products is higher, 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 antiviral ursolic acid derivative and a preparation method thereof. Background technique [0002] Judging from the antiviral drugs currently used or to be used clinically, long-term and high-dose use of antibiotics will cause drug resistance to the virus, which makes clinicians face problems such as refractory viral infection and viral rebound after drug resistance , Some patients will also experience adverse reactions such as gastrointestinal discomfort. Therefore, improving the efficacy of viral drugs and reducing the amount or period of use of antiviral drugs is of great significance for the use of antiviral drugs and disease treatment. Studies in recent years have shown that some natural plant extracts and their derivatives have antiviral effects. In addition to the antiviral effects of western medicine, these extracts can also reduce adverse reactions durin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61P31/16
CPCA61P31/16C07J63/008
Inventor 籍建亚
Owner 籍建亚
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