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Biphenylamide compound with antitumor activity, preparation method and application thereof

An anti-tumor activity, biphenylamide technology, applied in the field of biomedicine, can solve the problems of drug resistance, chemical drugs cannot achieve therapeutic effect, uncontrollable toxic and side effects, etc., and achieves cheap reagents, mild reaction conditions, and easy raw materials. the effect

Inactive Publication Date: 2016-01-20
XI AN JIAOTONG UNIV
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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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  • Biphenylamide compound with antitumor activity, preparation method and application thereof
  • Biphenylamide compound with antitumor activity, preparation method and application thereof
  • Biphenylamide compound with antitumor activity, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] In the structural formula of this compound, R 1 is a hydrogen atom, R 2 It is an alkoxy group with 3 carbon atoms, and the end is substituted by dimethylamino, prepared by the following steps (see figure 1 ):

[0049] 1) 3-bromophenol (1) is prepared by benzylation reaction compound 1-benzyloxy-3-bromobenzene (2)

[0050] Dissolve 15.57g (90mmol) of 3-bromophenol (1) in 300ml of absolute ethanol, add 37.32g (270mmol) of anhydrous potassium carbonate, stir at room temperature for ten minutes, then add 11.50ml (99mmol) of benzyl chloride, heat to reflux React for 5 hours. After the reaction is completed, cool to room temperature and suction filter, the filtrate is decompressed to recover ethanol, then add ethyl acetate for extraction, the organic phase is washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, water, saturated sodium chloride solution, and finally the organic phase After drying with anhydrous sodium sulfate, the solvent was...

Embodiment 2

[0074] where R 1 is a hydrogen 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

[0075] Steps 1) to 6) are the same as in Example 1, that is, the compound 6-benzyloxy-3'-hydroxyl-5-methoxybiphenyl-2-benzene is prepared from the starting compound 3-bromophenol (1) Formic acid (8), and 4-[2-(4-aminophenoxy) propyl] morpholine (11) 1.07g (4.6mmol) by condensation reaction to prepare 3',6-dibenzyloxy-5- Methoxy-N-[4-(3-morpholin-4-ylpropoxy)phenyl]biphenyl-2-carboxamide (12) 1.33 g, yield 53%. The target compound 3', 6-dihydroxyl-5-methoxy-N-[4-(3-morpholin-4-ylpropoxy)phenyl]biphenyl-2-carboxamide was prepared by reduction reaction ( BPA-6) 0.89g, yield 92%.

[0076] The structure of the resulting compound is shown below:

[0077]

[0078] Physical and chemical properties: m.p.: 145~148℃.EI-MS(m / z): 478.2[M]+

[0079] BPA-61H NMR (400MHz, DMSO) δ7.65 (d, J = 8.0Hz, 1H), 7.43 (d, J = 8...

Embodiment 3

[0081] where R 1 is a fluorine atom, R 2 It is an alkoxy group with 2 carbon atoms, and the end is substituted by dimethylamino, prepared by the following steps

[0082] Steps 1) to 6) are the same as in Example 1, that is, the compound 6-benzyloxy-3'-hydroxyl-5-methoxybiphenyl-2-benzene is prepared from the starting compound 3-bromophenol (1) Formic acid (8), then with 2-(4-amino-2-fluorophenoxy) ethyl] dimethylamine (9) 0.91g (4.6mmol) by condensation reaction to prepare N-{4-[2-( Dimethylamino)ethoxy]-3-fluorophenyl}-3',6-dibenzyloxy-5-methoxy-2-carboxamide (17) 1.23g, yield 52%. The target compound N-{4-[2-(dimethylamino)ethoxy]-3-fluorophenyl}-3',6-dihydroxy-5-methoxy-2-methyl was prepared by reduction reaction Amide (BPA-7) 0.81g, yield 93%.

[0083] The structure of the resulting compound is shown below:

[0084]

[0085] Physical and chemical properties: m.p.:183~185℃.EI-MS(m / z):440.0[M]+

[0086] BPA-71H NMR (400MHz, DMSO) δ7.94(s, 1H), 7.25(d, J=8.0Hz, 1H), ...

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Abstract

The invention discloses a biphenyl amide 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 amide via an oxygen atom. 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 biphenyl amide 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 biphenylamide 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/64C07C231/12C07D295/088A61K31/167A61K31/5375A61K31/4453A61K31/40A61K35/00
Inventor 贺浪冲张杰张涛卢闻李鹏飞王嗣岑潘晓艳
Owner XI AN JIAOTONG UNIV