Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Linolenic acid-metronidazole compound and its preparation method and application

A technology of metronidazole and linolenic acid, which is applied in the field of medicine, can solve the problems of easy drug resistance, and achieve the effects of stable acidic environment, high specificity of action, and low resistance to drugs

Active Publication Date: 2022-02-01
右江民族医学院
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Technical problem solved: In order to solve the problem that Helicobacter pylori is easily resistant to metronidazole and improve the antibacterial effect of metronidazole on drug-resistant Helicobacter pylori, the invention provides a linolenic acid-metronidazole compound and its preparation Method and application, the prepared linolenic acid-metronidazole has good inhibitory effect on metronidazole-resistant Helicobacter pylori, and is not easy to produce drug resistance, has specific inhibitory effect, stable acidic environment, and can be used as a treatment Drugs of choice for Helicobacter pylori infection

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Linolenic acid-metronidazole compound and its preparation method and application
  • Linolenic acid-metronidazole compound and its preparation method and application
  • Linolenic acid-metronidazole compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Step 1: Add 139mg of linolenic acid, 5ml of DCM, and 103mg of DCC condensing agent into a 25ml reaction bottle, stir at room temperature for 5 minutes, add 94mg of metronidazole, 0.5mL of triethylamine as a base, and 5mg of DMAP as a catalyst, and react at room temperature overnight. The molar ratio of raw materials linolenic acid and metronidazole is 1:1.1.

[0024] Step 2: TLC detects that the raw material of linolenic acid disappears completely, and white precipitate precipitates out of the system, and is filtered with diatomaceous earth. After the filtrate was spin-dried, column chromatography gave linolenic acid-metronidazole, about 105 mg, as a yellow oily liquid, yield: 48.7%. The product was identified as linolenic acid-metronidazole by NMR, mass spectrometry and infrared.

Embodiment 2

[0026] Step 1: Add 139mg of linolenic acid, 5ml of DCM, and 106mg of DCC condensing agent into a 25ml reaction bottle, stir at room temperature for 8 minutes, add 104mg of metronidazole, 0.6mL of triethylamine as a base, and 5mg of DMAP as a catalyst, and react at room temperature overnight. The molar ratio of raw materials linolenic acid and metronidazole is 1:1.2.

[0027] Step 2: TLC detects that the raw material of linolenic acid disappears completely, and white precipitate precipitates out of the system, and is filtered with diatomaceous earth. After the filtrate was spin-dried, column chromatography gave linolenic acid-metronidazole, about 102.8 mg, as a yellow oily liquid, yield: 45.3%. The product was identified as linolenic acid-metronidazole by NMR, mass spectrometry and infrared.

Embodiment 3

[0029] Step 1: Add 139mg of linolenic acid, 5ml of DCM, and 108mg of DCC condensing agent into a 25ml reaction bottle, stir at room temperature for 6 minutes, add 94mg of metronidazole, 0.6mL of triethylamine as a base, and 5mg of DMAP as a catalyst, and react at room temperature overnight. The molar ratio of raw materials linolenic acid and metronidazole is 1:1.1.

[0030] Step 2: TLC detects that the raw material of linolenic acid disappears completely, and white precipitate precipitates out of the system, and is filtered with diatomaceous earth. After the filtrate was spin-dried, column chromatography gave linolenic acid-metronidazole, about 103 mg, as a yellow oily liquid, yield: 46.5%. The product was identified as linolenic acid-metronidazole by NMR, mass spectrometry and infrared.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

Linolenic acid-metronidazole compound and its preparation method and application, adding linolenic acid, dichloromethane, dicyclohexylcarbodiimide condensing agent in a reaction vessel, after stirring at room temperature for 5 minutes, adding metronidazole, triethylamine ( As a base), 4-dimethylaminopyridine was used as a catalyst, and the reaction was carried out at room temperature overnight. Thin-layer chromatography (TLC) detected that the raw material of linolenic acid disappeared completely, and the system had a white precipitate, which was filtered through diatomaceous earth. The filtrate was spin-dried to obtain a metronidazole-linolenic acid esterified product by column chromatography. The invention successfully prepares the linolenic acid-metronidazole compound with a high yield of 48.7%, and the compound has a good inhibitory effect on Helicobacter pylori in vivo and in vitro, especially Helicobacter pylori resistant to metronidazole , Can promote the repair of gastric mucosal inflammation in mice; it is stable in an acidic environment, has low cytotoxicity, and has strong specificity; it is not easy to develop drug resistance, and can be used as the first choice for the treatment of Helicobacter pylori.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a linolenic acid-metronidazole compound and its preparation method and application. Background technique [0002] Helicobacter pylori (Hp) is a Gram-negative bacterium with a helical shape, microaerophilicity, and harsh growth conditions. Studies have shown that Hp infection can lead to acute and chronic gastritis, gastric and duodenal ulcers, gastric cancer, lymphoproliferative gastric lymphoma and other diseases, and is related to the incidence of liver cancer outside the intestinal tract and diabetes. At present, the treatment plan for Hp infection is triple or new quadruple therapy, that is, taking "proton pump inhibitors (omeprazole, etc.) + two antibiotics (from clarithromycin, amoxicillin, tetracycline, metronidazole, etc.) at the same time." Choose two)" or "bismuth (bismuth potassium citrate, etc.) + proton pump inhibitors (omeprazole, etc.) + two antibiotics (from c...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/92A61P31/04A61P1/04
CPCC07D233/92A61P31/04A61P1/04
Inventor 黄衍强戴园园赵丽娟李如佳覃春黄干荣覃艳春
Owner 右江民族医学院
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com