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Benzamide compound with antitumor activity as well as preparation method and application thereof

A technology of anti-tumor activity and benzamide, which is applied in the field of biomedicine, can solve the problems of uncontrollable side effects, inability to achieve therapeutic effects of chemical drugs, and drug resistance, and achieve cheap reagents, mild reaction conditions, and easy raw materials. The effect

Inactive Publication Date: 2014-08-13
XIAN HONGHUI HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many deficiencies in antineoplastic drugs, such as uncontrollable toxic and side effects, rapid drug resistance, etc., which lead to the inability of chemical drugs to achieve the expected therapeutic effect

Method used

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  • Benzamide compound with antitumor activity as well as preparation method and application thereof
  • Benzamide compound with antitumor activity as well as preparation method and application thereof
  • Benzamide compound with antitumor activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In the structural formula of this compound, R 1 is a hydrogen atom, R 2 It is an alkoxy group with 2 carbon atoms, and the end is substituted by a morpholinyl group, prepared by the following steps (see figure 1 ):

[0041] 1) 3-Hydroxy-4-methoxybenzaldehyde (1) Preparation of compound 3-benzyloxy-4-methoxybenzaldehyde (2) by benzylation reaction

[0042]Dissolve 4.56g (30mmol) of 3-hydroxy-4-methoxybenzaldehyde (1) in 120mL of absolute ethanol, add 12.44g (90mmol) of anhydrous potassium carbonate, stir at room temperature for ten minutes, add 5.20mL (45mmol) Benzyl chloride was heated to reflux for 5 hours. After the reaction is completed, cool to room temperature and filter, the filtrate is decompressed to recover ethanol, then add 140mL ethyl acetate for extraction, the organic phase is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution successively, and finally the organic phase is washed wit...

Embodiment 2

[0056] where R 1 is a fluorine atom, R 2 It is an alkoxy group with 3 carbon atoms, and the end is substituted by dimethylamino, prepared by the following steps

[0057] Steps 1) to 2) are the same as in Example 1, that is, the compound 3-benzyloxy-4-methoxybenzoic acid (3-benzyloxy-4-methoxybenzoic acid (3 ), and then with [3-(4-amino-2-fluorophenoxy) propyl] dimethylamine (6) to prepare N-{4-[3-(dimethylamino) propoxy] through condensation reaction -3-fluorophenyl}-3-benzyloxy-4-methoxybenzamide (7), the specific embodiment is:

[0058] Dissolve 0.98g (3.8mmol) of 3-benzyloxy-4-methoxybenzoic acid (3) in 100mL of anhydrous tetrahydrofuran, then add 1.46g (7.6mmol) of EDCI and 0.77g (5.7mmol) of HOBT in sequence, DMAP0.24g, triethylamine 5mL, continue to stir for 15min after the dropwise addition, then add dropwise 0.97g (4.6mmol) [3-(4-amino-2-fluorophenoxy)propyl]dimethyl 30 mL of anhydrous tetrahydrofuran solution of baseamine (6), and stirred at room temperature for 8...

Embodiment 3

[0064] where R 1 is a fluorine atom, R 2 It is an alkoxy group with 3 carbon atoms, and the end is substituted by a morpholinyl group, prepared by the following steps

[0065] Steps 1) to 2) are the same as in Example 1, that is, the compound 3-benzyloxy-4-methoxybenzoic acid (3-benzyloxy-4-methoxybenzoic acid (3 ), and then prepare N-[3-fluoro-4-(3-morpholine- 4-ylpropoxy)phenyl]-3-benzyloxy-4-methoxybenzamide (7), the specific embodiment is:

[0066] Dissolve 0.98g (3.8mmol) of 3-benzyloxy-4-methoxybenzoic acid (3) in 100mL of anhydrous tetrahydrofuran, then add 1.46g (7.6mmol) of EDCI and 0.77g (5.7mmol) of HOBT in sequence, DMAP0.24g, triethylamine 5mL, continue to stir for 15min after the dropwise addition, then add dropwise 1.16g (4.6mmol) [3-fluoro-4-(3-morpholin-4-ylpropoxy) to the reaction solution 30 mL of anhydrous tetrahydrofuran solution of phenyl]amine (6), stirred at room temperature for 8 hours after the dropwise addition was completed. After the reaction ...

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Abstract

The invention discloses a benzamide compound with antitumor activity as well as a preparation method and application thereof. The structural formula of the compound is shown in the specification, wherein in the structural formula, R1 is hydrogen or halogen; R2 is alkoxy with carbon number of 1-4; the terminal of R2 is replaced by tert-amido; R2 is linked to the para-position of benzamide via oxygen atoms; R3 is one of hydroxyl or methoxyl; R4 is the other one of hydroxyl or methoxyl. The compound has good tumor cell inhibiting activity in vitro and can be used for preparing antitumor drugs, especially anti-hepatoma drugs and anti-breast cancer drugs. The preparation method of the benzamide compound, provided by the invention, has the advantages that the raw materials are accessible, the reaction conditions are mild, the reaction process is simple to operate, and the used reagent is cheap.

Description

technical field [0001] The invention relates to the technical field of biomedicine, relates to an anti-tumor compound, in particular to a benzamide compound with anti-tumor activity and its preparation method and application. Background technique [0002] Malignant tumor is one of the main diseases that seriously affect human health and threaten human life. Statistics from the World Health Organization show that millions of people die from malignant tumors every year in the world, and it has become the second largest killer of human diseases after cardiovascular and cerebrovascular diseases. Chemotherapy, as one of the important means of treating tumors, has undergone tremendous development and progress in the past three decades, and a large number of clinical antitumor drugs with different mechanisms of action have been obtained. However, there are still many deficiencies in antineoplastic drugs, such as uncontrollable toxic and side effects, rapid drug resistance, etc., w...

Claims

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Application Information

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IPC IPC(8): C07C235/56C07C231/12C07D295/088A61K31/5375A61K31/167A61K31/40A61K31/4453A61P35/00
Inventor 张杰贺浪冲张涛李鹏飞卢闻王嗣岑潘晓艳
Owner XIAN HONGHUI HOSPITAL
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