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

Disubstituted allyl benzene derivatives as well as preparation and uses thereof

A technology of substituents and compounds, applied in the field of disubstituted phenylpropene derivatives and their preparation and use, can solve the problems of unsatisfactory, limited universal applicability of drugs, malignant killing of normal cells and the like

Inactive Publication Date: 2011-10-05
ZHEJIANG HISUN PHARMA CO LTD
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the specific drugs for the treatment of tumor diseases are not satisfactory, and the malignant killing of normal cells caused by the low selectivity of cytotoxic drugs currently used in anti-tumor clinics limits the general applicability of such drugs

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
  • Disubstituted allyl benzene derivatives as well as preparation and uses thereof
  • Disubstituted allyl benzene derivatives as well as preparation and uses thereof
  • Disubstituted allyl benzene derivatives as well as preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Preparation of compound IV-d (3,4-bis(4-ethoxybenzyloxy)-benzaldehyde)

[0066]

[0067] This example relates to a general synthesis method of a class of 3,4-disubstituted phenylpropene derivative key intermediates 3,4-disubstituted benzaldehyde series compounds with cytotoxic activity shown in formula (IV). It specifically relates to the synthesis of compound 3,4-bis(4-ethoxybenzyloxy)-benzaldehyde. In a 25 mL three-necked flask, a solution of p-ethoxybenzyl bromide (400 mg, 1.86 mmol) in N,N-dimethylformamide (4.0 mL) was added to potassium carbonate (200 mg, 1.45 mmol ) and 3,4-dihydroxybenzaldehyde (100 mg, 0.72 mmol) in N,N-dimethylformamide (4.0 ml) mixture, refluxed for 3 hours. Cooled to room temperature, filtered, and the filtrate was concentrated and passed through the column to obtain 180 mg of white solid with a yield of 61.2%.

[0068] Compound IV-d: white solid, melting point: 98-100°C, R f (n-hexane / ethyl acetate: 1 / 1) 0.73; 1 H NMR (40...

Embodiment 2

[0069] Example 2: Preparation of compound IV-c (3,5-bis(4-ethoxybenzyloxy)-benzaldehyde)

[0070]

[0071] This example relates to a general synthesis method of a class of 3,5-disubstituted phenylpropene derivative key intermediate 3,5-disubstituted benzaldehyde series compounds having cytotoxic activity shown in formula (IV). It specifically relates to the synthesis of compound 3,5-bis(4-ethoxybenzyloxy)-benzaldehyde. Add 3,5-bis(4-ethoxybenzyloxy)-benzohydrazide (1.05 g, 2.41 mmol), tetrabutylammonium bromide (0.78 g, 2.41 mmol), ammonia (25%, 2.4 milliliters) and benzene (20 milliliters), were added dropwise to potassium ferricyanide solution, and after stirring for 1 hour, the product was extracted with an organic solvent, and the filtrate was concentrated and passed through a column to obtain 250 milligrams of a white solid , the yield was 22.1%.

[0072] Compound IV-c: white solid, melting point: 97-99°C, R f (n-hexane / ethyl acetate: 3 / 1): 0.40; 1H NMR (400MHz, C...

Embodiment 3

[0073] Example 3: Preparation of compound IV-e (2,4-bis(4-ethoxybenzyloxy)-benzaldehyde)

[0074]

[0075] This example relates to a general synthesis method of a class of 2,4-disubstituted phenylpropene derivative key intermediate 2,4-disubstituted benzaldehyde series compounds having cytotoxic activity shown in formula (IV). It specifically relates to the synthesis of compound 2,4-bis(4-ethoxybenzyloxy)-benzaldehyde. In a 25 mL three-necked flask, a solution of p-ethoxybenzyl bromide (400 mg, 1.86 mmol) in N,N-dimethylformamide (4.0 mL) was added to potassium carbonate (200 mg, 1.45 mmol ) and 2,4-dihydroxybenzaldehyde (100 mg, 0.72 mmol) in N,N-dimethylformamide (4.0 ml) mixture, refluxed for 3 hours. Cool to room temperature, filter, concentrate the filtrate, and recrystallize from chloroform and methanol to obtain 150 mg of IV-e colorless crystals, with a yield of 51.0%.

[0076] Compound IV-e: colorless crystals, melting point: 116-118°C, R f (n-hexane / ethyl acet...

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
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to the discovery and application of a plurality of drug lead compounds, in particular to a bis-substituted allyl benzene compound with cytotoxic activity, the key intermediate and the pharmaceutical salt of the compound, also to the preparation method, the drug composition and the medicinal purpose of the allyl benzene derivative and the key intermediate of the allyl benzenederivative, belonging to the fields of organic chemistry, medicinal chemistry and pharmacology. The compound of the discovery in vitro inhibits the activity of six human tumor cell lines-human prostate cancer cells (PC-3), nasopharyngeal carcinoma cells (CNE), oral epithelial carcinoma cells (KB), human lung cancer cells (A549), human hepatoma cells (BEL-7404) and human cervical cancer cells (Hela), and can be expected for antitumor drug purpose.

Description

technical field [0001] The present invention relates to the fields of organic chemistry, medicinal chemistry and pharmacology. Specifically, the present invention relates to the preparation method of disubstituted phenylpropene derivatives and key intermediates thereof, and the effects of this series of compounds on six human tumor cell lines such as Human prostate cancer cells (PC-3), nasopharyngeal carcinoma cells (CNE), oral epithelial cancer cells (KB), human lung cancer cells (A549), human liver cancer cells (BEL-7404), human cervical cancer cells (Hela ) for tumor cell growth inhibitory activity screening. The compounds are found to have a certain activity of inhibiting the growth of tumor cells, and can be expected to be used as antitumor drugs. technical background [0002] At present, due to environmental pollution and other problems brought about by industrial development, the quality of human living environment continues to decline, and the incidence and mortalit...

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): C07C47/575C07C69/708C07C59/66A61K31/11A61K31/19A61K31/216A61P35/00
Inventor 赵昱王晓雨曾苏巫秀美白骅
Owner ZHEJIANG HISUN PHARMA CO LTD
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