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2,3,4,5-tetrasubstituted derivatives of benzyl ethylene class, preparation method and application

A technology of four-substitution and derivatives, which is applied in the field of 2,3,4,5-tetrasubstituted phenylpropene derivatives and their preparation and application, and can solve the problems of limited drug universal applicability, low selectivity, and ineffective curative effect. Satisfactory etc.

Inactive Publication Date: 2007-10-10
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the curative effect of drugs for the treatment of tumor diseases is not satisfactory. At present, the anti-tumor drugs used in clinical practice are generally cytotoxic drugs, and their low selectivity leads to malignant killing of normal cells, which limits the general applicability of such drugs.

Method used

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  • 2,3,4,5-tetrasubstituted derivatives of benzyl ethylene class, preparation method and application
  • 2,3,4,5-tetrasubstituted derivatives of benzyl ethylene class, preparation method and application
  • 2,3,4,5-tetrasubstituted derivatives of benzyl ethylene class, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Embodiment 1: the preparation of V-c (2-bromo-3,5-dimethoxy-4-(3,4-dichlorobenzyloxy) benzaldehyde)

[0078]

[0079] This example relates to a class of 2,3,4,5-tetrasubstituted phenylpropene derivative key intermediate 2,3,4,5-tetrasubstituted benzene with cytotoxic activity shown in formula (V) General synthesis method of formaldehyde series compounds. It specifically relates to the synthesis of compound 2-bromo-3,5-dimethoxy-4-(3,4-dichlorobenzyloxy)benzaldehyde. The compound 2-bromo-4-hydroxyl-3,5-dimethoxybenzaldehyde (0.85 g, 3.28 mmol) was dissolved in 20 ml of acetone, anhydrous potassium carbonate (1.13 g, 8.22 mmol) was added, and stirred for 10 minutes , and then added 3,4-dichlorobenzyl bromide (0.6 ml, 3.61 mmol) in 10 ml of acetone, and refluxed for 4 hours. Thin-layer chromatography (TLC) showed that the reaction of the raw material was basically complete, cooled to room temperature, filtered to remove potassium carbonate, and distilled off the solve...

Embodiment 2

[0081] Embodiment 2: the preparation of compound V-a (2,3,5-trimethoxy-4-(4-ethoxybenzyloxy) benzaldehyde)

[0082]

[0083] This example relates to a class of 2,3,4,5-tetrasubstituted phenylpropene derivative key intermediate 2,3,4,5-tetrasubstituted benzene with cytotoxic activity shown in formula (V) General synthesis method of formaldehyde series compounds. It specifically relates to the synthesis of compound 2,3,5-trimethoxy-4-(4-ethoxybenzyloxy)benzaldehyde. Add p-ethoxybenzyl bromide (0.51 g, 2.37 mmol) sodium iodide (59 mg, 0.40 mmol) and acetone (15 ml) successively in a 100 ml three-necked flask, then add potassium carbonate (0.82 g, 5.94 mmol) and 4-hydroxy-2,3,5-trimethoxybenzaldehyde (420 mg, 1.98 mmol), refluxed for 3 hours. Cool to room temperature, filter, concentrate the filtrate, and purify by column chromatography (petroleum ether / ethyl acetate=15:1, crude product / silica gel=1:30) to obtain 363 mg of white solid with a yield of 53%.

[0084] Compound V...

Embodiment 3-6

[0085] According to the method with one of embodiment 1-2, prepare embodiment 3-6 compound shown in following table 1:

[0086]

[0087] Table I

[0088]

[0089] List the physicochemical data of each compound in Table 1 below:

[0090] Compound V-b: white solid, Rf (n-hexane / ethyl acetate: 5 / 2) 0.57; 1 H-NMR (400MHz, CDCl 3 ): δ10.29 (1H, s, CHO), 7.62 (1H, d, J=2.0Hz, H-2′), 7.43 (1H, d, J=8.0Hz, H-5′), 7.29 (1H , m, J=8.0, 2.0Hz, H-6'), 7.11 (1H, s, H-6), 5.11 (2H, s, H-7'), 3.93 (3H, s, OCH 3 -2), 3.86 (6H, s, OCH 3 -3, 5).

[0091] Compound V-d: white solid, Rf (n-hexane / ethyl acetate: 5 / 2) 0.51; 1 H-NMR (400MHz, CDCl 3 ): δ10.26 (1H, s, CHO), 7.34 (2H, d, J=8.8Hz, H-3′, 5′), 7.26 (1H, s, H-6), 6.84 (2H, d, J=8.8Hz, H-2', 6'), 5.05(2H, s, H-7'), 4.00(2H, q, J=6.8Hz, OCH 2 CH 3 -4'), 3.87 (6H, s, OCH 3 -3, 5), 1.38 (3H, t, J=6.8Hz, OCH 2 CH 3 -4′).

[0092] Compound V-e: colorless liquid, Rf (n-hexane / ethyl acetate: 5 / 2) 0.61; 1 H-NMR (400MHz, CDCl3): δ...

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Abstract

This invention relates to 2, 3, 4, 5-tetrasubstituted phenyl propylene derivatives with cytotoxicity. This invention also relates to a method for preparing the derivatives, their drug compositions, and their pharmaceutical application. The derivatives can inhibit the bioactivity of prostate cancer cell (PC-3), nasopharyngeal cancer cell (CNE), oral epithelial cancer cell (KB), lung cancer cell (A549), liver cancer cell (BEL-7404), and cervical cancer cell (Hela), thus can be used as anti-tumor drugs.

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 2,3,4,5-tetrasubstituted phenylpropenoid derivatives and key intermediates thereof, and for this series of compounds Six tumor cell lines were carried out, such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cell line (CNE), oral epithelial cancer cell line (KB), human lung cancer cell (A549), human liver cancer cell (BEL-7404 ), human cervical cancer cell (Hela) 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. Background of the invention [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 inci...

Claims

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Application Information

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IPC IPC(8): C07C69/708C07C47/575A61K31/216A61P35/00
Inventor 赵昱张丽娟曾苏巫秀美白骅
Owner ZHEJIANG HISUN PHARMA CO LTD
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