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Ring-A polyoxidizing substituted glycyrrhetinic acid derivative and preparation method and application thereof

A technology of glycyrrhetic acid and derivatives, which is applied in the field of A-ring polyoxidatively substituted glycyrrhetic acid derivatives and their preparation, and can solve problems such as unreported anti-tobacco mosaic virus activity.

Active Publication Date: 2014-07-16
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that some triterpenes and triterpene saponins have strong anti-tobacco mosaic virus activity, and glycyrrhetinic acid has strong anti-animal virus activity, but its anti-tobacco mosaic virus activity has not been reported

Method used

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  • Ring-A polyoxidizing substituted glycyrrhetinic acid derivative and preparation method and application thereof
  • Ring-A polyoxidizing substituted glycyrrhetinic acid derivative and preparation method and application thereof
  • Ring-A polyoxidizing substituted glycyrrhetinic acid derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0169] Embodiment 1 of the present invention: preparation of compound G-1:

[0170] Take 3.00g (6.38mmol) of glycyrrhetinic acid in a 250ml round bottom flask, add 100ml of N,N-dimethylformamide (DMF) to dissolve it completely, add 1.00g (7.25mmol) of potassium carbonate powder, at room temperature After stirring for 15 min, 7.0 mmol of benzyl bromide was added, and the reaction was refluxed under nitrogen protection. TLC (thin layer chromatography) was used to detect the reaction progress (developing solvent: V (petroleum ether): V (acetone) = 5: 1) until the reaction was completed. After 2 hours of reaction, the reaction liquid was extracted with ethyl acetate after adding water, and the organic layer was first washed with saturated NaHCO 3 The pH of the solution was adjusted to 7, then washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain a crude yellow oil. Silica gel colum...

Embodiment 2

[0172] Embodiment 2: the preparation of compound G-b:

[0173] Take 3.00g (5.35mmol) of compound G-1 in a 500ml round bottom flask, dissolve it in 200ml of absolute ethanol, add 40.00g of zinc powder, stir in an ice bath, and slowly drop in 100ml of hydrochloric acid until the reaction is complete. After 5 hours of reaction, the unreacted zinc powder was removed by filtration, and the filtrate was poured into 500ml of ice water and left to stand for 2 hours. The precipitate was precipitated, and the white precipitate was obtained by suction filtration, and recrystallized from methanol to obtain 2.40 g of compound G-b, with a yield of 82.2%.

[0174] Compound G-b, colorless needles, C 37 h 54 o 3 , mp160~162℃; IR(KBr),σ / cm -1 :3424,2926,2871,1727,1638,1454,1383,1313,1215,1151,1085,1044,1029,995,740,695; 1 H NMR (400MHz, CDCl 3 )δ: 7.36-7.30 (m, 5H, H-Ar), 5.17 (brt, 1H, J=3.6Hz, H-12), 5.18 (d, 1H, J=12.0Hz, Bn-CHH'), 5.08 (d,1H,J=12.0Hz,Bn-CHH'),3.22(dd,1H,J=5.2Hz,10.8Hz...

Embodiment 3

[0175] Embodiment 3: the preparation of compound G-2:

[0176] Take 2.20g (3.93mmol) of compound G-1 in a 250ml round bottom flask, add 100ml of acetone to dissolve, stir in an ice bath for 15min, then slowly add 10.68ml (4.00mmol) of the Jones reagent that is now prepared, react at room temperature under nitrogen protection, TLC Detection of reaction progress (V (petroleum ether): V (ethyl acetate) = 6: 1), 2h reaction is complete. Use 2mol / L sodium hydroxide solution to adjust the pH of the reaction solution to neutral to terminate the reaction, evaporate acetone under reduced pressure, add water to disperse, extract with ethyl acetate, and the organic layer is sequentially washed with saturated NaHCO 3 The solution was washed with saturated NaCl solution, dried over anhydrous magnesium sulfate, filtered, and the solvent was distilled off under reduced pressure to obtain the crude product as a colorless powder. Recrystallization from methanol gave 22.11 g of compound G-2 wi...

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Abstract

The invention discloses a ring-A polyoxidizing substituted glycyrrhetinic acid derivative and a preparation method and application thereof. The compound has the formula shown in the specification, wherein R1 is selected from carbonyl or hydroxyl; R2 and R3 are hydroxyl or an epoxy group exists between R2 and R3; R4 is selected from -COOH, -COOR1, -CONH2, -CONHR1 and -CONR1R2; R1 and R2 are selected from alkyl with 1-15 carbon atoms, substituted or unsubstituted phenyl, substituted or unsubstituted phenyl alkyl, and R1 and R2 can be same or different; Y is CH2 or C=O; hydrogen in the 18th site is alpha or beta-configuration; when R1, R2 and R3 are hydroxyl, the hydroxyl substituent configurations can be alpha or beta-configurations. The compound with a novel structure, which is provided by the invention, and the salt thereof have relatively strong hepatoprotective activity and can be used for preparing hepatoprotective medicines. The derivative has the application of resisting bacteria or tobacco mosaic virus, and has good application prospects in the fields of medicines and pesticides.

Description

technical field [0001] The invention relates to A-ring polyoxidized substituted glycyrrhetinic acid derivatives, a preparation method and application thereof, and belongs to the technical field of medicinal chemistry. Background technique [0002] The liver is an important metabolic organ and barrier organ, and liver disease seriously threatens human health and life. Liver disease is a common and frequently-occurring disease. The pathogenic factors include viruses, bacteria, chemicals, alcohol, high-fat diet, etc., among which viral hepatitis is dominant. Chronic hepatitis B is the main cause of liver cirrhosis and liver cancer. According to statistics, there are about 130 million chronic hepatitis B virus carriers in my country, accounting for 10% of the country's total population; 25% to 40% of chronic hepatitis patients eventually die of liver cirrhosis or liver cancer; drug-induced hepatitis and alcoholic liver cirrhosis The incidence rate is also high. Therefore, the ...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07J71/00A61P1/16A61P31/04A01P1/00A01P3/00
Inventor 黄丽荣杨小生李齐激骆衡郝小江
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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