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

Bromo nitryl dihydroxy diphenyl ether compound and its synthesis method

A technology of bromonitrodihydroxydiphenyl ether and nitrodihydroxydiphenyl ether, which is applied in the field of bromonitrodihydroxydiphenyl ether compounds and their synthesis, can solve the problem of unsatisfactory antibacterial activity, Harm and other issues, to achieve the effect of reducing dosage and side effects, low cost, and safety of people and the environment

Inactive Publication Date: 2007-05-30
CHENGDU MEDICAL COLLEGE
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compared with the reference substance 2,4,4'-trichloro-2'-hydroxydiphenyl ether, the antibacterial activity of this compound is not satisfactory, and some are even lower than the reference substance, and the antibacterial compound is used The process may also produce dioxin-like toxic substances that have great harm to humans and the environment

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
  • Bromo nitryl dihydroxy diphenyl ether compound and its synthesis method
  • Bromo nitryl dihydroxy diphenyl ether compound and its synthesis method
  • Bromo nitryl dihydroxy diphenyl ether compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of intermediate 2-nitro-4,4'-bisacetoxydiphenyl ether

[0033] Add 2.54g (0.0126mol) 4,4′-dihydroxydiphenyl ether, 4.84g (0.04674mol) acetic anhydride (≥98.5%) into a 100mL three-necked flask with a magnetic stirrer, thermometer and reflux condenser. , Heat to reflux, monitor the reaction progress by TLC, after the reaction, cool the solution to room temperature, then add 4.85g (0.0468mol) acetic anhydride (≥98.5%) to the solution, stir well, slowly add 2.44g (0.0252mol) ) Concentrated HNO 3 (65%), react at room temperature, check the end of the reaction by TLC, after the reaction, use saturated NaHCO 3 Adjust the pH of the solution to 5-6, then extract the aqueous solution with ethyl acetate (3×20ml), separate the organic layer, and use anhydrous CaCl 2 After drying overnight, filtering, and removing the solvent under reduced pressure, a brown granular substance was obtained with a yield of 82.0%. Example 2: Synthesis of intermediate 2-nitro-4,4'-dihyd...

Embodiment 2

[0034] Add 4.17g (0.0126mol) 2-nitro-4,4'-bisacetoxydiphenyl ether, 30ml of 20% NaOH solution, 3ml into a 100mL three-necked flask equipped with a magnetic stirrer, thermometer and reflux condenser Ethanol, heat to reflux, monitor the reaction progress by TLC, after the reaction, adjust the pH to 1-3 with concentrated HCl, then extract the aqueous solution with ethyl acetate (3×20ml), separate the organic layer, and dry overnight with anhydrous sodium sulfate , Filtered, and the solvent was removed under reduced pressure to obtain a dark brown granular crude product. The crude product was separated by column chromatography to obtain a light brown solid material with a yield of 90.0%.

Embodiment 3

[0035] Example 3: Synthesis of target compound 3-bromo-2'-nitro-4,4'-dihydroxydiphenyl ether and detection of biological activity

[0036] Add 0.50g (0.0020mol) 2-nitro-4,4′-dihydroxydiphenyl ether and 2.64g (0.04mol / L) ice into a 100mL three-necked flask with a magnetic stirrer, thermometer and reflux condenser. Acetic acid, heat to reflux, dissolve 0.37g (0.0023mol) liquid bromine in 2.64g (0.04mol / L) glacial acetic acid, slowly drip into a three-necked flask, and react under reflux. TLC detects the end of the reaction, and the reaction until the red color basically fades , Cool to room temperature, use NaHCO 3 Adjust pH5-6, with 3%~5%Na 2 S 2 O 3 Wash with an aqueous solution to remove unreacted bromine, dry, evaporate the solvent, and recrystallize the crude product with petroleum ether to obtain the light yellow crystal target with a yield of 75.0%; 1 HNMR(CDCl 3, 400MHz) δ: 5.343 (s, 1H, OH), 5.512 (s, 1H, OH), 6.919 (dd, J=8.8, 2.8Hz, 1H, ArH), 6.970 (d, J=8.8Hz, 1H, ArH), ...

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 discloses a bromonitro dihydroxy diphenyl ether compound and synthesizing method, which is characterized by the following: adopting 4, 4'-dihydroxy diphenyl ether as raw material; reacting through three-step to obtain bromo-2-nitro-4, 4'-dihydroxy diphenyl ether compound; selecting large intestine Escherichia and kala diplococcus to detect bacteriostatic activity to synthesize bromodihydroxy diphenyl ether; avoiding the fault of high toxic dioxins compound.

Description

Technical field [0001] The invention relates to an antibacterial drug compound and a synthesis method thereof. Specifically, the invention relates to a bromonitrodihydroxydiphenyl ether compound and a synthesis method thereof. Background technique [0002] Natural polybrominated-2,2'-dihydroxydiphenyl ether (structure I) has good antibacterial activity (Tetrahedron, 1981, 37, 2335; J. Nat. Prod, 1995, 58, 1384), and natural bromine The new compound with similar basic structure of -2,2'-dihydroxydiphenyl ether also has a strong killing effect on many harmful bacteria (Organic Chemistry 2006, 26(10), 1335). The invention patent with publication number CN 1281574C discloses "a nitro bromide hydroxy diphenyl ether compound and its synthesis method", which is achieved by introducing a nitro bromide 2-hydroxy diphenyl ether bactericide into the molecular structure Base, and obtain a bacteriostatic target with low environmental pollution, cheap and easy-to-obtain raw materials, and high...

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): C07C201/08C07C205/38A61P31/04A01P3/00
Inventor 辛莹王玉良陈鸶
Owner CHENGDU MEDICAL COLLEGE
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