Method for synthesizing anticancer compound CA4

A synthesis method, CA4 technology, applied in the field of synthesis of anticancer compound CA4, can solve the problems of increasing synthesis steps and production costs

Inactive Publication Date: 2007-10-10
TIANJIN UNIV
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In these routes, it is necessary to protect the phenolic hydroxyl group with silicon ether, or to use a noble metal catalyst, thus increasing the synthesis steps and production costs.

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
  • Method for synthesizing anticancer compound CA4
  • Method for synthesizing anticancer compound CA4
  • Method for synthesizing anticancer compound CA4

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add 1.654g 3,4,5-trimethoxybenzyltriphenylphosphonium bromide salt, 0.400g 3-hydroxyl-4-methoxybenzaldehyde, 0.545g potassium carbonate, 35mL ethanol in a 100mL flask, Under protection, it was heated to reflux for 8 h, and TLC (developing agent chloroform:ethyl acetate=8:1) showed that the reaction was complete. Spin off ethanol, add ethyl acetate, acidify with 20mL of 5% hydrochloric acid, wash twice with water, wash the organic phase once with saturated sodium bisulfite, dry the organic layer with anhydrous sodium sulfate, filter off sodium sulfate, and reduce the reaction solution to Concentrate under pressure to obtain an oil. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1 as eluent), and the fraction containing CA4 was collected to obtain 0.800 g of the product with a yield of 96%. Utilize HPLC to carry out the qualitative and separation of components (wavelength: 254nm, mobile phase: methanol / water=60 / 40)...

Embodiment 2

[0019] In the flask of 100mL, add 1.654g 3,4,5-trimethoxybenzyltriphenylphosphonium bromide salt, 0.400g 3-hydroxyl-4-methoxybenzaldehyde, 0.220g potassium hydroxide, 35mL ethanol, in Under the protection of nitrogen, it was heated to reflux for 6 h, and TLC (developing solvent: chloroform: ethyl acetate = 8: 1) showed that the reaction was complete. Spin off ethanol, add ethyl acetate, acidify with 20mL of 5% hydrochloric acid, wash twice with water, wash the organic phase once with saturated sodium bisulfite, dry the organic layer with anhydrous sodium sulfate, filter off sodium sulfate, and reduce the reaction solution to Concentrate under pressure to obtain an oil. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1 as the eluent), and the fraction containing CA4 was collected to obtain 0.803 g of the product with a yield of 97%. Utilize HPLC to carry out the qualitative and separation of components (wavelength: 254nm,...

Embodiment 3

[0021]Add 1.654g 3,4,5-trimethoxybenzyltriphenylphosphonium bromide salt, 0.400g 3-hydroxyl-4-methoxybenzaldehyde, 0.545g potassium carbonate, 35mL water in a 100mL flask, Under protection, it was heated to reflux for 10 h, and TLC (developing agent chloroform:ethyl acetate=8:1) showed that the reaction was complete. Add ethyl acetate for extraction, acidify with 20 mL of 5% hydrochloric acid, wash twice with water, wash the organic phase once with saturated sodium bisulfite, dry the organic layer with anhydrous sodium sulfate, filter off sodium sulfate, and concentrate the reaction solution under reduced pressure to obtain Oil. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate = 5:1 as eluent), and the fraction containing CA4 was collected to obtain 0.591 g of the product with a yield of 71%. Utilize HPLC to carry out the qualitative and separation of components (wavelength: 254nm, mobile phase: methanol / water=60 / 40), by inte...

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

This invention relates to a method for synthesizing an anti-tumor compound CA4. The method comprises: dissolving substituted benzyl triphenyl phosphonium halide and substituted aromatic aldehyde in a solvent, heating under the effect of alkali to synthesize hydroxyl-substituted diphenyl ethylene compound, removing the solvent, acidifying, extracting with an organic solvent, washing the organic phase with saturated sodium hydrogen sulfite solution, washing with water, drying, and performing silica gel column chromatography to obtain a mixture of cis-CA4 and trans-CA4. The method has such advantages as simple process and mild reaction conditions (no need for low-temperature and anhydrous conditions).

Description

field of invention [0001] The invention relates to the synthesis of anticancer compounds, in particular to a method for synthesizing anticancer compound CA4, that is, condensing substituted benzyltriphenylphosphonium halides and substituted aromatic aldehydes into anticancer compound CA4 under alkaline conditions. Background technique [0002] The World Health Organization survey results show that cancer patients are increasing year by year, and the annual global death toll is as high as more than 6 million. It has become the second largest killer after cardiovascular disease and greatly endangers human health. The number of cancer deaths in my country has increased from about 700,000 per year in the 1970s to about 1.2 million, and the number of deaths has increased to about 900,000, and it is still showing a sharp upward trend. Cancer is one of the major diseases that seriously endanger human health, and chemical drug therapy is still the main treatment. [0003] CA4 is a ...

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): C07C43/23C07C41/26C07C41/30
Inventor 李春葆张丹
Owner TIANJIN 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