Substituted benzyl ethylene derivant and method of preparing the same and use thereof

A derivative, the technology of phenylpropylene, applied in the field of preparation of phenylpropylene derivatives, can solve the problems of limiting the universal applicability of drugs, malignant killing of normal cells, and unsatisfactory, and achieves feasible market prospects, low cost, The effect of the simple synthesis method

Inactive Publication Date: 2008-01-23
ZHEJIANG UNIV
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  • 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

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  • Substituted benzyl ethylene derivant and method of preparing the same and use thereof
  • Substituted benzyl ethylene derivant and method of preparing the same and use thereof
  • Substituted benzyl ethylene derivant and method of preparing the same and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 : Preparation of important intermediate I-f (4-(4-ethoxybenzyloxy)-benzaldehyde)

[0033]

[0034] This example relates to the general synthesis method of substituted benzaldehyde series compounds which are key intermediates of substituted phenylpropene derivatives with cytotoxic activity. It specifically relates to the synthesis of compound I-f (4-(4-ethoxybenzyloxy)-benzaldehyde). Dissolve syringaldehyde (298 mg, 1.6 mmol) in 20 ml of acetone, add anhydrous potassium carbonate (567 mg, 4.1 mmol), stir for ten minutes, and then add p-ethoxybenzyl bromide (537 mg, 2.5 mmol) 10 ml of acetone solution, reflux for 4 hours. Thin-layer chromatography (TLC) analysis showed that the reaction of the raw material was basically complete, cooled to room temperature, filtered to remove potassium carbonate, and distilled off the solvent acetone. The crude product obtained after concentration was separated by column chromatography to obtain 281 mg of white solid with ...

Embodiment 2

[0036] Example 2 : the preparation of important intermediate I-g (3-[4-(4-ethoxybenzyloxy group) phenyl]-2-propenoic acid ethyl ester (2E))

[0037]

[0038]This example involves the general synthesis of substituted phenylacrylates with cytotoxic activity. It specifically relates to the synthesis of compound I-g (3-[4-(4-ethoxybenzyloxy)phenyl]-2-propenoic acid ethyl ester (2E)). Compound I-f (256 mg, 1.0 mmol) was dissolved with pyridine (5 mL) in a 100 mL three-necked flask, added dropwise into 0.2 mL of piperidine, and monoethyl malonate (198 mg, 1.5 mmol) was added, Reflux for 2 hours. Cool to room temperature, add 2M hydrochloric acid to neutralize pyridine, partition and extract with water and ethyl acetate, concentrate the organic layer, and purify by column chromatography (petroleum ether / ethyl acetate=6:1, crude product / silica gel=1:30) to obtain a white solid , the yield was 75.1%.

[0039] Compound I-g: white solid, melting point: 103-104°C, Rf (n-hexane / eth...

Embodiment 3

[0040] Example 3 : the preparation of compound I-a (3-[4-(4-ethoxybenzyloxy) phenyl]-2-propene-1-alcohol (2E))

[0041]

[0042] Lithium aluminum hydride (387 mg, 10.2 mmol) and aluminum trichloride (427 mg, 32.0 mmol) were placed in a three-necked flask, 10 ml of tetrahydrofuran was added under the protection of an inert gas, cooled to 0 ° C in an ice-salt bath, and added by implementing Compound I-g (3-[4-(4-ethoxybenzyloxy)phenyl]-2-propenoic acid ethyl ester (2E)) obtained in Example 2 was 1.043 g (3. mmol), and stirred for 1.5 hours. Add water to decompose excess lithium aluminum hydride, then adjust the pH to acidic with 1M hydrochloric acid, extract with ethyl acetate, wash the organic phase with saturated brine, dry overnight with anhydrous sodium sulfate, filter, concentrate the filtrate to obtain a crude product, and purify by column chromatography ( Petroleum ether / ethyl acetate=4:1, crude product / silica gel=1:50) to get 3-[4-(4-ethoxybenzyloxy)phenyl]-2-propen...

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Abstract

A substituted benzene propylene derivative and the salt are provided, which is that the phenylacrylate substituted by the corresponding group gains the correspondingly substituted phenylallyl compound through the deoxidization of the lithium aluminium hydride and the aluminium trichloride compound. The invention has certain selective cytotoxicity activeness compound from the natural erucic based alcohol compound and has low toxic effect on the normal cells, while the compounds reconstructed by structure and the important midbodies all have better cytotoxicity activeness and can be prepared in the drugs preventing and curing the tumor diseases. The prepared drugs contain the drug excipients or carriers allowed by the preparation. The drug preparation is in a form of liquid, solid, aerial fog spray, drop, gelatin pearl, nano, controlled release and sustained-release preparation. The compound related to by the invention has simple synthetic method and lower cost, therefore having feasible marketalization prospect. The invention has the above general formula.

Description

technical field [0001] The present invention relates to the field of organic chemistry, specifically, to the preparation method of substituted phenylpropene derivatives, and the series of compounds to six kinds of tumor cell lines, such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cell ( CNE), oral epithelial cancer cell lines (KB), human lung cancer cells (A549), human liver cancer cells (BEL-7404), and human cervical cancer cells (Hela). 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. Background technique [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 mortality of tumor diseases are also increasing. However, the specific drugs for the treatment of tumor diseases are not satisfactory, and the malignant killing of no...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/26C07C43/295C07C217/82A61K31/085A61K31/136A61P35/00
Inventor 赵昱吴昊张丽娟邹宏斌约阿施·史托克希特巫秀美
Owner ZHEJIANG UNIV
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