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Biphenyl compound with anti-tumor activity and preparation method thereof

A technology of anti-tumor activity and compounds, applied in the field of biomedicine, can solve the problems of tumor chemotherapy not meeting expectations, toxic and side effects of chemotherapy drugs, etc., and achieve the effect of cheap and easy-to-obtain reagents, easy-to-source, and simple operations

Inactive Publication Date: 2011-11-16
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the different degrees of toxic and side effects of chemotherapy drugs and the emergence of drug resistance of tumors, chemotherapy of tumors often fails to achieve the desired effect.

Method used

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  • Biphenyl compound with anti-tumor activity and preparation method thereof
  • Biphenyl compound with anti-tumor activity and preparation method thereof
  • Biphenyl compound with anti-tumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] R in the structural formula of embodiment 1 1 , R 2 Compounds that are both 3-chloro-4-fluorohalogens, prepared by the following steps:

[0033] 2-Chloro-N-(3-chloro-4-fluorophenyl)acetamide

[0034] 1) isovanillin (1) prepared by bromination reaction compound 2-bromoisovanillin (2)

[0035] Put 20.0g (0.132mol) of isovanillin (1), 21.59g (0.263mol) of sodium acetate and 0.68g (0.012mol) of iron powder into a 500mL three-necked flask, add 120ml of glacial acetic acid, and stir at room temperature for 30min;

[0036] After the stirring is completed, add dropwise the solution prepared by mixing 7.0mL (0.14mol) liquid bromine and 30mL glacial acetic acid in advance under the condition that the temperature is controlled at 23-25°C. ;

[0037] Then add 250 mL of ice water, stir for 1 h; filter, evaporate the solid to dryness, and recrystallize from ethanol to obtain 24.59 g of an off-white solid product of 2-bromoisovanillin (2), with a yield of 81%;

[0038] Its physic...

Embodiment 2

[0069] R in the structural formula of embodiment 2 1 for hydrogen, R 2 Is the compound of 4-hydroxyl, prepared by the following steps:

[0070]Steps 1) to 6) are the same as in Example 1, that is, from compound isovanillinization (1) to compound 5,5'-dimethoxy-6,6'-dihydroxybiphenyl-2,2'- The preparation steps of dimethylformamide (7) are the same; afterwards, in the different etherification processes of the two phenolic hydroxyl groups, the two phenolic hydroxyl groups react successively with chloroacetanilide and chloroacetyl 4-hydroxyaniline, specifically:

[0071] Dissolve 3.60g (10mmol) of compound 5,5'-dimethoxy-6,6'-dihydroxybiphenyl-2,2'-dicarboxamide in (7) 200mL of anhydrous acetone, add 4.15 g (30 mmol) of anhydrous potassium carbonate, stirred at room temperature for 30 minutes, added 1.86 g (11 mmol) of 2-chloro-N-(phenyl)acetamide, and heated at reflux at 56°C for 8 hours;

[0072] After the reaction is complete, evaporate the solvent under reduced pressure, d...

Embodiment 3

[0077] R in the structural formula of embodiment 3 1 is 3-chloro-4-hydroxyl, R 2 is 3-chloro-4-fluoro-5-amino compound, prepared by the following steps:

[0078] Steps 1) to 6) are the same as in Example 1, that is, from compound isovanillinization (1) to compound 5,5'-dimethoxy-6,6'-dihydroxybiphenyl-2,2'- The preparation steps of dimethylamide (7) are identical; afterwards, in the different etherification processes of the two phenolic hydroxyl groups, the two phenolic hydroxyl groups are successively reacted with 2-chloro-N-(3-chloro-4-hydroxyphenyl) acetamide and 2-Chloro-N-(3-chloro-4-fluoro-5-aminobenzene)acetamide reaction, specifically:

[0079] Dissolve 3.60g (10mmol) of compound 5,5'-dimethoxy-6,6'-dihydroxybiphenyl-2,2'-dicarboxamide in (7) 200mL of anhydrous acetone, add 4.15 g (30 mmol) of anhydrous potassium carbonate, stirred at room temperature for 30 minutes, added 2.42 g (11 mmol) of 2-chloro-N-(3-chloro-4-hydroxyphenyl)acetamide, and heated at reflux for 8...

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Abstract

The invention discloses a biphenyl compound with anti-tumor activity and a preparation method thereof, the biphenyl compound shows the anti-tumor activity both in vitro and in vivo, which can induce apoptosis and inhibit proliferation of a cell line for colorectal cancer, lung cancer, liver cancer, breast cancer or pancreatic cancer in vitro, and inhibit tumor for the liver cancer and the colorectal cancer in vivo, so that the biphenyl compound can be applied in the preparation of anti-tumor drugs. The preparation method of the biphenyl compound has the advantages of easy obtainment of sources of raw materials, mild reaction conditions, simple operation of the reaction process, and cheap and easy obtainment of used reagents.

Description

technical field [0001] The invention relates to the technical field of biomedicine, relates to an antitumor compound, in particular to a biphenyl compound with antitumor activity and a preparation method thereof. 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 there are about 10 million cancer patients in the world every year, and millions of people die of malignant tumors. Malignant tumors have become the second largest killer of humans next to cardiovascular diseases. Chemotherapy of tumors is one of the three basic means of cancer prevention and treatment. After decades of development, the research on chemotherapeutic drugs for tumor treatment has achieved great success, and a large number of clinical anti-tumor drugs with different mechanisms of action have been obtained. However, due to the different degrees of toxic and side ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/46C07C231/12A61K31/167A61P35/00
CPCC07C231/14C07C235/46C07C235/84A61P35/00
Inventor 贺浪冲张杰张彦民贺怀贞王嗣岑李西玲卢闻王红英
Owner XI AN JIAOTONG UNIV
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