Ursolic acid derivative capable of protecting gastric mucosa and preparation method thereof

A technology of ursolic acid and derivatives, applied in the field of chemical drug synthesis, can solve problems such as damage to gastric mucosa, unfavorable transdermal administration, gastrointestinal irritation and the like

Inactive Publication Date: 2021-08-06
张洪胜
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the carboxyl contained in the structure makes ursolic acid an acidic drug. If the acidic drug is directly administered orally, it will cause great irritation to the gastrointestinal tract and damage the gastric mucosa; The ability of acid transdermal absorption is weak, which is more unfavorable for transdermal drug delivery
In addition, the presence of carboxyl groups in ursolic acid increases the polarity of ursolic acid, which affects the absorption of drugs in the body, so that the blood lipid-lowering biological activity of ursolic acid cannot be fully utilized.

Method used

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  • Ursolic acid derivative capable of protecting gastric mucosa and preparation method thereof
  • Ursolic acid derivative capable of protecting gastric mucosa and preparation method thereof
  • Ursolic acid derivative capable of protecting gastric mucosa and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Dissolve 20g of ursolic acid in 60mL of N,N-dimethylformamide, add 5.2g of acetyltriphenylphosphorus chloride, heat to 40°C, react for 2h, filter, and rinse the filter cake with absolute ethanol Wash, dry over anhydrous magnesium sulfate, obtain compound A;

[0027] (2) Dissolve 10g of compound A and 7.5g of sitosterol in 100mL of pyridine, the temperature is controlled at 35°C, then add 0.25g of 4-dimethylaminopyridine, carry out esterification reaction for 5h under stirring, filter, and extract the filtrate with hexane , the organic phase was washed successively with saturated brine, saturated sodium bicarbonate solution and water, dried with anhydrous calcium chloride and concentrated to remove the solvent to obtain a crude product, which was purified by silica gel column chromatography to obtain the target compound. The yield was 81.59%.

[0028] H NMR spectrum detection:

[0029] Put the sample into the sample tube, and inject 0.5mL CDCL3 (deuterated chlorofo...

Embodiment 2

[0030] Embodiment 2 The compound of the present invention is to the impact of absolute ethanol type ulcer in rats

[0031] Tested animals: SPF grade SD rats, body weight 180±20g, half male and half female. Before the test, the male and female mice were fed separately for 7 days and then the test was started. The room temperature was (25±2)°C, and the humidity was 67±13%.

[0032] Test method: healthy SD rats are randomly divided into normal control group (control group 1), model group (control group 2), cimetidine positive control group (control group 3), experimental group (embodiment 1 target compound ). The normal group and the model group were given equal volumes of distilled water, and the rest of the groups were fed for 7 days, once a day, fasted for 48 hours after the sixth administration, and 2 hours after the last administration, the rest except the normal control group Each group was fed with absolute ethanol, and then the rats were killed, their stomach tissues wer...

Embodiment 3

[0038] Embodiment 3 The effect of compound of the present invention on rat glacial acetic acid type gastric ulcer

[0039] SPF grade SD rats, fasted for 24 hours, anesthetized with 10% chloral hydrate injection, cut the abdominal wall and gently removed the rat’s stomach, and placed a glass tube with an inner diameter of 5mm vertically on the gastric serosa After 15 minutes, use a fine cotton swab to absorb the acetic acid in the glass tube, wipe it gently with a cotton swab of 0.9% sodium chloride solution for 2 times, and then cover the smeared surface of the acetic acid with the greater omentum, and lightly wipe the stomach Gently send it back to the abdominal cavity, and suture the peritoneal membrane and all layers of the abdominal wall. In the sham operation control group, only the stomach was pulled out for 15 minutes after laparotomy. The rats were randomly divided into a sham operation group (control group 1), a model group (control group 2), a cimetidine positive co...

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Abstract

The invention discloses an ursolic acid derivative capable of protecting gastric mucosa and a preparation method thereof, and the preparation method comprises the following steps: dissolving ursolic acid in an organic solvent, and carrying out substitution and esterification with a halogenating agent to obtain the ursolic acid derivative; an animal gastric ulcer model test proves that the ursolic acid derivative has a relatively good treatment effect on gastric ulcer and can play a certain protection effect on gastric mucosa; the preparation method has the advantages of simple process steps, cheap and easily available raw materials and reusable solvent, and is suitable for industrial development.

Description

technical field [0001] The invention belongs to the technical field of chemical drug synthesis, and relates to an ursolic acid derivative for protecting gastric mucosa and a preparation method thereof. Background technique [0002] Ursolic acid, also known as ursolic acid or ursolic acid, belongs to triterpenoids and is widely found in Chinese herbal medicines and foods. Ursolic acid has various biological effects such as anti-inflammatory and anti-bacterial, anti-diabetic, lowering blood sugar, anti-ulcer, and protecting gastric mucosa. Sitosterol, also known as β-sitosterol (Beta-Sitosterol), belongs to the tetracyclic three-tiered compound, which is a natural compound present in plants, fruits and nuts. However, the carboxyl contained in the structure makes ursolic acid an acidic drug. If the acidic drug is directly administered orally, it will cause great irritation to the gastrointestinal tract and damage the gastric mucosa; The ability of transdermal absorption of ac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P1/04
CPCC07J63/008A61P1/04
Inventor 张洪胜
Owner 张洪胜
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