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Compounds of class of styracin and cinepazid ester phenylpropionic acid, prepration method and application

A technology of phenylacrylic acid phenylpropylene and phenylacrylic acid, which is applied in drug combination, organic chemistry, drug delivery, etc., can solve the problems of limiting the universal applicability of drugs, low selectivity, and malignant killing of normal cells

Inactive Publication Date: 2006-07-05
ZHEJIANG HISUN PHARMA CO LTD
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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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  • Compounds of class of styracin and cinepazid ester phenylpropionic acid, prepration method and application
  • Compounds of class of styracin and cinepazid ester phenylpropionic acid, prepration method and application
  • Compounds of class of styracin and cinepazid ester phenylpropionic acid, prepration method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0092] A further embodiment of the present invention is:

[0093] When the substituent X in the compound of formula (3) is oxygen, the substituent R is ethoxy (CH 3 CH 2 O) during, as shown in formula (4), be formula I-1 compound:

[0094] Formula (4)

[0095] where substituent R 6 , R 7 , R 8 The definition of is the same as formula (3).

[0096] Compounds of formula I-1 of the present invention include:

[0097] I-1-a. (E)-7-methoxyl ethyl phenylpropionate;

[0098] I-1-b. (E)-6,7-Dimethoxymethoxy-ethyl phenylpropionate;

[0099] I-1-c. (E)-6,8-dimethoxy-7-O-(4'-bromobenzyl)-phenylpropionic acid ethyl ester;

[0100] I-1-d. Ethyl (E)-7-nitrophenylpropionate;

[0101] I-1-e. (E) - ethyl 7-methoxymethoxyphenylpropionate;

[0102] I-1-f. (E)-6,8-dimethoxy-7-O-(2'-fluoro, 4'-bromobenzyl)-phenylpropionic acid ethyl ester;

[0103] I-1-g. (E)-6,7-dimethoxy-ethyl phenylpropionate;

[0104] I-1-h. ethyl cinnamate;

[0105] I-1-i. (E)-6,8-dimethoxy-7-O-(3'-bromobenzyl...

Embodiment 1

[0155] Example 1: Preparation of Compound I-i ((E)-(7-methoxymethoxy)phenylpropionic acid-(E)-(7'-methoxymethoxy)phenylpropenyl ester)

[0156]

[0157] This example relates to the general synthesis of compounds of formula (1) with cytotoxic activity. It specifically relates to the synthesis of compound (E)-(7-methoxymethoxy)phenylpropanoic acid-(E)-(7'-methoxymethoxy)phenylpropenyl ester. Dissolve p-methoxymethoxycinnamic acid (292mg, 1.4mmol), N,N-dicyclohexylcarbodiimide (318mg, 1.5mmol), 4-dimethylaminopyridine (34mg, 0.28mmol) in dichloro In methane, it was stirred at room temperature for 10 minutes, and white turbidity appeared, and a dichloromethane solution of p-methoxymethoxycinnamyl alcohol (300 mg, 15 mmol) was added, and stirred at room temperature for 24 hours. Celite was filtered, the filtrate was concentrated, and the crude product was separated by column chromatography (n-hexane / ethyl acetate=8:1, crude product / silica gel=1:50) to obtain 468 mg of a white s...

Embodiment 2-19

[0159] According to the method of Example 1, the compounds of Examples 2-19 shown in the following Table 1 were prepared:

[0160]

[0161] implement

Example number

compound

Numbering

substituent

R 6

R 7

R 8

R 6′

R 7′

R 8′

2

I-a

H

OCH 3

H

H

OCH 3

H

3

I-b

OCH 3

OCH 3

OCH 3

H

OCH 3

H

4

I-c

H

NO 2

H

OCH 3

OCH 3

H

5

I-d

OCH 3

OCH 3

OCH 3

OCH 3

OCH 3

OCH 3

6

I-e

H

OCH 3

H

OCH 3

OCH 3

H

7

I-f

OCH 3

OCH 3

H

OCH 3

OCH 3

H

[0162]

[0163] List the physicochemical data of each compound in Table 1 below:

[0164] Compound I-a:

[0165] White solid, melting point: 63-64°C, Rf (n-hexane / ethyl acetate: 3 / 1): 0.71; ...

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Abstract

This invention relates to a cytotoxic phenylallyl phenylacrylate as shown in formula (1) and its analogs or phenylpropyl phenylpropionate as shown in formula (2), its analogs and its offcinal salts or solvates. This invention also relates to the preparation method for these compounds and the intermediates for preparation. Besides, this invention still relates to the pharmacological use of these compounds and their blended composites. The compounds in this invention have growth inhibitory activity towards tumor cells and are estimated to be used as antineoplastics.

Description

field of invention [0001] The present invention relates to the field of organic chemistry, medicinal chemistry and pharmacology, specifically, the present invention relates to phenylpropenyl phenylacrylate and phenylpropyl phenylpropionate and phenylpropionate propylphenyl ester compounds and their key intermediates and their preparation Methods and their use as medicines. 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 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 normal cells caused by the low selectivity of cytotoxic drugs currently used in anti-tumor clinics limits the general applicability of such drugs. Therefore, searching for and discovering new highly selective cytotoxic antit...

Claims

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Application Information

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IPC IPC(8): C07C69/734C07C69/612C07C205/56C07C229/40A61K31/216A61K9/02A61K9/06A61K9/12A61K9/20A61K9/08A61K9/10A61P35/00
Inventor 赵昱周长新白骅胡利红邹宏斌巫秀美
Owner ZHEJIANG HISUN PHARMA CO LTD
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