Bromolaminarin-containing oxamide with anticancer activity and its synthesis method and application

A technology of lamininate and oxalamide, which is applied in the field of bromine-containing laminadinate and its synthesis, can solve the problems of NIK-3T3 toxicity and other problems, and achieve the goal of promoting apoptosis, precise treatment and better effect Effect

Active Publication Date: 2020-07-31
QINGDAO UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, researchers have screened and developed the anti-tumor activity of algae in the coastal area of ​​Shandong. Although the extract of Ulva ulva has high cytotoxic activity against human coelomoma KB cells and HT-29 cells, it is also effective against normal human cells. Cell NIK-3T3 also has greater toxicity

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
  • Bromolaminarin-containing oxamide with anticancer activity and its synthesis method and application
  • Bromolaminarin-containing oxamide with anticancer activity and its synthesis method and application
  • Bromolaminarin-containing oxamide with anticancer activity and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] (1) Synthesis of N-(5-bromo-2-carboxyanilino) oxalyl ethyl ester: Dilute 40mmol (5.49g) ethyl oxalate monoacyl chloride with 10mL of anhydrous tetrahydrofuran (THF) and place in an ice bath Slowly added dropwise to 40 mL of anhydrous THF solution dissolved with 4-bromo-2-aminobenzoic acid equimolar to oxalic acid monoacyl chloride (8.72 g), and kept in ice bath for 30 min. Then the temperature rose slowly to 60°C, and a white precipitate precipitated out of the solution. The reaction was continued for 3h, and the solution was filtered, washed with ice ethanol and ether several times, and dried in vacuo to obtain a white solid N-(5-bromo-2-carboxyanilino ) oxalyl ethyl ester 8.77g, yield 69.6%.

[0029] (2) Synthesis of 6-N,N,N-trimethyl-2-aminocaproic acid methyl ester hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 2h, add 50mmol (1.60g) of methanol, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to n...

Embodiment 2

[0033](1) Synthesis of N-(5-bromo-2-carboxyanilino) oxalyl ethyl ester: Dilute 40mmol (5.49g) ethyl oxalate monoacyl chloride with 10mL of anhydrous tetrahydrofuran (THF) and place in an ice bath Slowly added dropwise to 40 mL of anhydrous THF solution dissolved with 4-bromo-2-aminobenzoic acid equimolar to oxalic acid monoacyl chloride (8.72 g), and kept in ice bath for 30 min. Then the temperature rose slowly to 60°C, and a white precipitate precipitated out of the solution. The reaction was continued for 3h, and the solution was filtered, washed with ice ethanol and ether several times, and dried in vacuo to obtain a white solid N-(5-bromo-2-carboxyanilino ) oxalyl ethyl ester 6.34g, yield 50.3%.

[0034] (2) Synthesis of 6-N,N,N-trimethyl-2-aminocaproic acid methyl ester hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 2h, add 50mmol (1.60g) of methanol, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to ne...

Embodiment 3

[0037] (1) Synthesis of N-(5-bromo-2-carboxyanilino) oxalyl ethyl ester: Dilute 40mmol (5.49g) ethyl oxalate monoacyl chloride with 10mL of anhydrous tetrahydrofuran (THF) and place in an ice bath Slowly added dropwise to 40 mL of anhydrous THF solution dissolved with 4-bromo-2-aminobenzoic acid equimolar to oxalic acid monoacyl chloride (8.72 g), and kept in ice bath for 30 min. Then the temperature rose slowly to 60°C, and a white precipitate precipitated out of the solution. The reaction was continued for 3h, and the solution was filtered, washed with ice ethanol and ether several times, and dried in vacuo to obtain a white solid N-(5-bromo-2-carboxyanilino ) 8.53g of ethyl oxalate, yield 67.7%.

[0038] (2) Synthesis of 6-N,N,N-trimethyl-2-aminocaproic acid methyl ester hydrochloride: Reflux 10mmol (2.24g) lamininine hydrochloride in thionyl chloride for 2h, add 50mmol (1.60g) of methanol, continue to reflux for 5h, evaporate the excess solvent, adjust the pH value to neu...

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 synthetic method of a bromine-containing laminine ester oxamide having anti-cancer activity and a composition thereof. The method is characterized in that the novel bromine-containing laminine ester oxamide having anti-cancer activity is synthesized by using natural marine organism non-protein-laminine. The preparation process mainly comprises a synthetic process of N-(5-bromine-2-carboxyl anilino)oxalyl ethyl ester, a synthetic process of 6-N,N,N-trimethyl-2-methyl carbamate hydrochloride, and a synthetic process of bromine-containing laminine ester oxamide. The technical scheme develops high-added value application of natural sea resource, an in-vitro cytotoxic activity experiment proves that the composition has anti-cancer activity effect, is suitable for usagein field of anti-cancer drug development, and has large medical and pharmaceutical values.

Description

technical field [0001] The invention relates to the technical field of drug synthesis and application, and more specifically relates to a bromine-containing lamininic acid ester oxalamide with anticancer activity and its synthesis method and application. Background technique [0002] At present, cancer is one of the main diseases that cause human death, killing more than 7 million people worldwide every year. It is estimated that the number of cancer deaths worldwide will continue to rise, and may exceed 13.1 million by 2030. About 30% of the new drugs that have been developed and marketed in the world are derived from natural products. In recent years, the research on natural anticancer drugs from terrestrial sources has not achieved many exciting new results. Therefore, people have turned their attention to the ocean. Discovery of new anti-cancer drugs from the ocean. [0003] Laminin is an active amino acid with anticancer and antihypertensive activities derived from the...

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): C07C231/12C07C231/02C07C233/56A61P35/00
Inventor 李群李晓雯李子超高琪
Owner QINGDAO UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap