Supercharge Your Innovation With Domain-Expert AI Agents!

Benzoxazole compound and preparation method and application thereof

A technology for benzoxazoles and compounds, which is applied in the field of benzoxazoles and their preparation, can solve the problems that surface toxic proteins cannot be anchored, the infectivity of pathogenic bacteria is decreased, and the like, and achieve the effect of inhibiting the infection of Staphylococcus aureus.

Inactive Publication Date: 2015-07-22
SHANGHAI JIAO TONG UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the Sortase A gene of bacteria is knocked out, its surface toxic protein cannot be anchored to the cell wall, resulting in a significant decrease in the infectivity of pathogenic bacteria

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
  • Benzoxazole compound and preparation method and application thereof
  • Benzoxazole compound and preparation method and application thereof
  • Benzoxazole compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This embodiment relates to the preparation of methyl 2-hydroxybenzoate (IX)

[0042] Add 100mL of methanol to 10g of salicylic acid, control the temperature in the ice-salt bath at 0°C, slowly add 10mL of thionyl chloride dropwise, control the temperature at 0°C during the dropwise addition, and raise the temperature to 75°C for reflux reaction after the dropwise addition, after 16h , the reaction solution was cooled to room temperature, the reaction solution was concentrated, dissolved by adding 200mL ethyl acetate, and successively added 100mL saturated sodium bicarbonate solution, 100mL water and 100mL saturated brine to wash the organic layer, added anhydrous sodium sulfate to dry, concentrated the organic layer, 10.3 g of holly liquid was obtained, yield 94.5%.

Embodiment 2

[0044] Preparation of 3-nitro-2-hydroxybenzoic acid methyl ester (VIII)

[0045] Dissolve 10g of methyl 2-hydroxybenzoate and 7mL of 65% nitric acid in 150mL of dichloromethane, control the temperature in the ice-salt bath at 0°C, slowly add 10mL of concentrated sulfuric acid dropwise, control the temperature in the ice-salt bath at 0°C, and end the addition Finally, the reaction temperature was still controlled at 0°C. After 20 min, 150 mL of water was added to quench the reaction, followed by adding 150 mL of saturated sodium bicarbonate solution, 150 mL of water, and 150 mL of saturated brine to wash the organic layer, adding anhydrous sodium sulfate to dry, and concentrating the organic layer , separated by column chromatography with PE:EA=6:1 to obtain 3.8g of yellow solid with a yield of 29.3%.

Embodiment 3

[0047] Preparation of 3-amino-2-hydroxybenzoic acid methyl ester (VII)

[0048] Dissolve 3.5g of methyl 3-nitro-2-hydroxybenzoate and 350mg of palladium on carbon in 50mL of methanol, and react at room temperature under reflux in a hydrogen system. After 18 hours, filter, add anhydrous sodium sulfate to the filtrate to dry, and concentrate the reaction solution. 2.4 g of white solid was obtained by column chromatography with PE:EA=8:1, the yield was 82.5%.

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

The invention provides a benzoxazole compound. The structure of the benzoxazole compound is shown in the formula (I), wherein R1, R2, R3 and R4 are hydrogen, C1-C5 alkyl, benzyl, aryl or hetero aryl. The preparation method of the benzoxazole compound is carried out according to the following reaction route. Compared with the prior art, the benzoxazole compound has the benefits that the Sortase A protease of bacteroid is used as a target spot, a similar structure of a Sortase A substrate is constructed through the action mechanism of the known Sortase A and the cell wall of a host cell, and new compounds with benzoxazole and mother nucleus are synthesized; the new compounds carry out the test screening of Sortase A activity inhibition so as to try to find candidate compounds for effectively inhibiting staphylococcus aureus infection.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and in particular relates to a benzoxazole compound and its preparation method and application. Background technique [0002] In the past two decades, due to the clinical abuse of antibiotics in hospitals in our country, not only the rapid increase in medical expenses, but also the rapid increase and spread of the incidence of pathogenic bacterial infections in our country. Epidemiological studies have shown that Gram-positive bacteria are the most common pathogens causing nosocomial infections. Therefore, the development of more effective, safe and stable new drugs against Gram-positive bacterial infection has become an urgent need in the medical field. [0003] Sortase is a class of sulfhydryl transpeptidases commonly found in Gram-positive bacteria and bound to cell membranes. Among them, Sortase A is the first kind of sortase found in Staphylococcus aureus. Studies have shown ...

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 Applications(China)
IPC IPC(8): C07D263/57A61P31/04
CPCC07D263/57
Inventor 傅磊姜发琴包健张勇何宛邓欣贤
Owner SHANGHAI JIAO TONG UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com