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Oleanolic acid derivative for treating psoriasis and preparation method thereof

A technology of oleanolic acid and derivatives, which is applied in the field of chemical drug synthesis, and can solve the problems of human body irritating response and limited bioavailability application

Inactive Publication Date: 2021-07-30
张洪胜
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the large molecular weight and low water solubility of oleanolic acid limit its bioavailability and clinical application. At the same time, the carboxyl structure in oleanolic acid makes oleanolic acid an acidic drug. Drugs or skin administration, will produce irritating reactions to the human body

Method used

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  • Oleanolic acid derivative for treating psoriasis and preparation method thereof
  • Oleanolic acid derivative for treating psoriasis and preparation method thereof
  • Oleanolic acid derivative for treating psoriasis and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Dissolve 15g of oleanolic acid in 100mL of tetrahydrofuran, add 3.7g of borane dimethyl sulfide complex, reflux at a temperature of 0-5°C for 13-15 hours, raise the temperature to room temperature, filter to remove the precipitate, and concentrate the filtrate into an extract, rinse with water, then rinse with 10% ethanol for 2 to 8 BV, then rinse with 80% ethanol, and dry in vacuum;

[0025] (2) Dissolve the product of step (1) in 100 mL of dichloromethane, add benzenesulfonyl chloride, add sodium hydroxide, reflux at room temperature for 20-24 hours, filter, concentrate to remove the organic solvent, add saturated sodium bicarbonate solution, and use Petroleum ether was extracted 2 to 3 times, the petroleum ether layers were combined, dried with anhydrous magnesium sulfate, concentrated, and the concentrated product was subjected to silica gel column chromatography, and the mixture of ethyl acetate and acetone with a volume ratio of 10:1 was used as the eluent Gra...

experiment example 2

[0026] Experimental Example 2 Pharmaceutical Research of Oleanolic Acid Derivatives on Psoriasis

[0027] 1. Experimental method

[0028] Healthy mice of the Kunming species were selected, cultured in a suitable environment, anesthetized by intraperitoneal injection of 1% chloral hydrate (0.2mL / 20g), and the hair on the back of the mice was removed to form a naked area with a size of 2cm×3cm. The mice were randomly divided into: normal group (control group 1), model group (control group 2), halometasone group (control group 3), oleanolic acid group (control group 4), oleanolic acid derivatives group (experimental group). Normal group: 42 mg of Vaseline ointment was applied to the exposed parts of the mice every day; model group: 42 mg of imiquimod was applied to the exposed areas of the back of the mice once a day for 7 consecutive days; Halometasone group: the exposed parts of the mice were regularly treated in the morning Apply imiquimod 42mg / time, once a day, and halometa...

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Abstract

The invention discloses an oleanolic acid derivative for treating psoriasis and a preparation method thereof, and the preparation method comprises the following steps: adding oleanolic acid into a reaction container, reducing carboxyl into hydroxyl by using a borane dimethyl sulfide complex, and reacting with benzene sulfonyl chloride to obtain the oleanolic acid derivative, and pathological experiments show that the oleanolic acid derivative can significantly improve the skin inflammatory response of a mouse suffering from psoriasis and increase the content of inflammatory factors IL-17 and IFN-gamma related to psoriasis, and therefore the oleanolic acid derivative can be used for preparing the medicine for treating psoriasis and has good social benefits and economic benefits.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to an oleanolic acid derivative for treating psoriasis and a preparation method thereof. Background technique [0002] Oleanolic acid belongs to pentacyclic triterpenoids, widely exists in nature, and has a variety of significant biological activities. Studies have shown that oleanolic acid has a good effect on the treatment of psoriasis. However, the large molecular weight and low water solubility of oleanolic acid limit its bioavailability and clinical application. At the same time, the carboxyl structure in oleanolic acid makes oleanolic acid an acidic drug. Drugs or skin administration, will produce irritating reactions to the human body. The structure of oleanolic acid is modified to improve the bioavailability of oleanolic acid, reduce its own side effects, and maximize the medicinal value of oleanolic acid. Contents of the invention [0003] In order to sol...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P17/06
CPCC07J63/008A61P17/06
Inventor 张洪胜
Owner 张洪胜
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