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

Acridine-1, 2, 3-triazole type compound and preparation method and application thereof

A compound, triazole technology, applied in the field of medicine, achieves good medicinal value and significant anti-tumor activity in vitro

Active Publication Date: 2015-01-14
广西新桂环保科技集团有限公司
View PDF2 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no relevant report on the synthesis of acridine-1,2,3-triazole derivatives by connecting the structure of 1,2,3-triazole ring at the 9-position of the acridine ring

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
  • Acridine-1, 2, 3-triazole type compound and preparation method and application thereof
  • Acridine-1, 2, 3-triazole type compound and preparation method and application thereof
  • Acridine-1, 2, 3-triazole type compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of 2-methoxy-9-acridine (p-methoxyphenyl)-1,2,3-triazole, concrete steps are as follows:

[0025] 1) In a 250mL three-necked flask, add 5.20g (26mmol) of o-bromobenzoic acid, 4.19g (34mmol) of p-methoxyaniline, 7.5g (36.2mmol) of potassium carbonate and 0.3g (4.7mmol) of copper powder, and then Add 30 mL of isoamyl alcohol as a solvent, reflux at 140°C and stir for 2 hours. After the reaction, evaporate the solvent under reduced pressure, add 600 mL of water to the obtained residue, stir at 80°C for 20 minutes, filter while hot, wash the filter cake with water, and combine the water layers , the aqueous layer was acidified with concentrated hydrochloric acid to pH = 2, a large amount of light green precipitate was precipitated, filtered with suction, and the obtained solid was recrystallized with chloroform to obtain compound 1 with a yield of 79%;

[0026] 2) In a 100mL round-bottomed flask, add 4.38g (18mmol) of compound 1 and 14.37mL of phosphorus oxy...

Embodiment 2

[0036] Repeat Example 1, the difference is:

[0037] In step 1), change the consumption of potassium carbonate to 5.39g (26mmol), copper powder 0.17g (2.6mmol), replace isoamyl alcohol with n-amyl alcohol, change the temperature during reflux to 150°C, and combine the water The layer was acidified to pH=4 with concentrated hydrochloric acid;

[0038] In step 3), the amount of sodium azide was changed to 0.26g (4mmoL), and the temperature during the reaction was changed to 80°C;

[0039] In step 4), change the volume ratio of tert-butanol to water in the tert-butanol / water solution to 4:6.

[0040] Mass spectrometry, carbon spectrometry and infrared analysis were performed on the separated brown needle-like crystals, and it was determined to be 2-methoxy-9-acridine(p-methoxyphenyl)-1,2,3-triazole.

Embodiment 3

[0042] Repeat Example 1, the difference is:

[0043] In step 1), the temperature at reflux was changed to 160° C., and the combined aqueous layer was acidified to pH=1 with concentrated hydrochloric acid;

[0044] In step 4), the volume ratio of tert-butanol and water in tert-butanol / water solution was changed to 8:2, and the solvent for recrystallization was changed to methanol.

[0045] Mass spectrometry, carbon spectrometry and infrared analysis were performed on the separated brown needle-like crystals, and it was determined to be 2-methoxy-9-acridine(p-methoxyphenyl)-1,2,3-triazole.

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

PropertyMeasurementUnit
Volumeaaaaaaaaaa
Login to View More

Abstract

The invention discloses an acridine-1, 2, 3-triazole type compound and a preparation method and application thereof. The preparation method of the acridine-1, 2, 3-triazole type compound comprises the following steps: 1) performing ullmann reaction by taking o-bromobenzoic acid and p-methoxyaniline as raw materials, taking potassium carbonate and copper powder as catalysts and taking isoamyl alcohol or n-amyl alcohol as a solvent to obtain a compound 1; 2) cyclizing the compound 1 with phosphorus oxychloride to prepare a compound 2; 3) dissolving the compound 2 in DMF (dimethylformamide) and performing nucleophilic substitution reaction with sodium azide to prepare a compound 3; and 4) taking p-methoxyphenylacetylene, dissolving in a tert-butyl alcohol / water solution, adding vitamin C sodium, copper sulfate pentahydrate and the compound 3 to react, performing suction filtration, and recrystallizing for preparation. In-vitro anti-tumor test results show that the acridine-1, 2, 3-triazole type compound has significant in-vitro anti-tumor activity against three subjects, namely MGC80-3, BEL-7404 and T24, has relatively good potential medicinal values, and is expected to be used for preparing various anti-tumor medicines.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an acridine-1,2,3-triazole compound and a preparation method and application thereof. Background technique [0002] Tumor is still one of the most common and serious diseases that directly threaten human life in the world today. According to incomplete statistics, about 7 million people are newly diagnosed with cancer every year in the world, and more than 5 million people die of cancer every year. In my country, the incidence rate is 146.87 / 100,000, and the cumulative rate is 22.08%. The mortality rate was 85.06 / 100,000, and the accumulative rate was 12.94%. Therefore, the research and development of anticancer drugs has great application prospects. [0003] Acridine is a class of nitrogen-containing organic heterocyclic compounds that has received extensive attention. It has shown strong physiological activities in anti-tumor, anti-virus, anti-malarial, anti-bacterial, biolum...

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
IPC IPC(8): C07D401/04A61P35/00
CPCC07D401/04
Inventor 刘华钢霍丽妮
Owner 广西新桂环保科技集团有限公司
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