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

A kind of acetylhydrazone compound and preparation method thereof

A technology of compound and acetyl hydrazone, which is applied in the field of acetyl hydrazone compounds and its preparation, can solve the problems of in-depth research on compounds with antimicrobial activity, decreased drug treatment effect, and increased drug resistance, so as to solve bacterial drug resistance, The effect of low cost and easy availability of raw materials

Active Publication Date: 2019-08-23
LIUPANSHUI NORMAL UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide a kind of acetylhydrazone compound and its preparation method, aiming at solving the problem of drug resistance increase due to the abuse of drugs at present, leading to the decline or even loss of the therapeutic effect of drugs, and related research on compounds with antimicrobial activity in-depth questions

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
  • A kind of acetylhydrazone compound and preparation method thereof
  • A kind of acetylhydrazone compound and preparation method thereof
  • A kind of acetylhydrazone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0058] Such as figure 1 Shown: the preparation method of the acetylhydrazone compound of the embodiment of the present invention specifically comprises the following steps:

[0059] S101: Compound 1 reacts with methyl iodide in DMF at a temperature of 10°C to 50°C to prepare intermediate 2;

[0060] S102: intermediate 2 is reacted in an acetone-water solvent under an ice-water bath to obtain intermediate 3;

[0061] S103: intermediate 3 is reacted in a methanol-water mixed solvent under alkali catalysis at a temperature of 70°C to 90°C to prepare intermediate 4;

[0062] S104: intermediate 4 is reacted with urea at 140°C to 160°C to prepare intermediate 5,

[0063] S105: intermediate 5 is reacted with ethyl chloroacetate in DMF under alkali catalysis at a temperature of 50°C-60°C to prepare intermediate 6,

[0064] S106: intermediate 6 is reacted in absolute ethanol at a temperature of 70°C-90°C to prepare intermediate 7,

[0065] S107: Intermediate 7 and aromatic aldehyde...

Embodiment 1

[0072] Embodiment 1, preparation of 2-(1-methyl-6-chloro-2,4(1H,3H)-quinazolinedionyl) acetylhydrazone compounds shown in general formula I

[0073] 1, the preparation of intermediate 2 (methyl o-thaminobenzoate)

[0074]

[0075] In a 500mL flask with a drying tube, add 50.20g (0.33mol) of raw material 1 (methyl anthranilate), 26.58g (0.66mol) of sodium hydroxide, 100mL of dimethylformamide (DMF), and drop Add a mixture of 61.32g (0.43mol) of iodomethane and 100mL of DMF, add and react at room temperature for 1 hour, then heat to 45°C and react for 7 hours. After the reaction, cool to room temperature, add 200mL of water, and extract with ethyl acetate (5× 100 mL), combined the ethyl acetate extracts, dried over anhydrous magnesium sulfate, suction filtered, the filtrate was rotary evaporated to remove the solvent, and purified by column to obtain 29.50 g of intermediate 2 (light yellow liquid), with a yield of 54%.

[0076] 2. Preparation of intermediate 3 (2-amino-5-chl...

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 acetylhydrazone-based compounds and a preparation method thereof. The acetylhydrazone-based compounds are 2-(1-methyl-6-chloro-2,4 (1H, 3H)-quinazolinedione) acetylhydrazone-based compounds expressed by a general formula I. In-vitro antimicrobial activity tests find that the acetylhydrazone-based compounds have certain inhibitory activity on gram-positive bacteria (staphylococcus aureus, methicillin-resistant staphylococcus aureus and bacillus subtilis), gram-negative bacteria (escherichia coli, proteusbacillus vulgaris and pseudomonas aeruginosa), and fungi (candida albicans, aspergillus flavus, aspergillus fumigatus and cryptococcus neoformans), and some compounds have the inhibitory activity on some tested strains that is close and even prior to the inhibitory activity of the existing drug streptomycin sulfate polyoxin B, so that the compounds can be used for preparing antibacterial and / or antifungal drugs. The preparation method for the compounds is simple, the raw materials are easily available, and the cost is relatively low.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to an acetylhydrazone compound and a preparation method thereof. Background technique [0002] Antibacterial drugs are currently one of the most widely used drugs in clinical practice. However, due to the abuse of drugs, drug resistance increases and the therapeutic effect of drugs decreases or even loses. Therefore, it becomes valuable and meaningful to develop new antibacterial drugs. [0003] Schiff base compounds are widely used in medicine, pesticides, etc. and have obvious effects. They have a wide range of biological activities. There are also applications in insects, anti-inflammatory, etc. Therefore, the combination of acylhydrazone and quinazoline diketones is expected to obtain better antibacterial activity. Contents of the invention [0004] The object of the present invention is to provide a kind of acetylhydrazone compound and its preparation method, aiming at s...

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): C07D239/96A61K31/517A61P31/04A61P31/10
CPCC07D239/96Y02A50/30
Inventor 杨丹
Owner LIUPANSHUI NORMAL UNIV
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