Biphenyl compound serving as antitumor medicament and preparation method thereof

A technology of anti-tumor drugs and compounds, which is applied in the field of biomedicine, can solve the problems of unanticipated tumor chemotherapy, toxic and side effects of chemotherapy drugs, etc., and achieve the effect of cheap and easy-to-obtain reagents, simple operation of the reaction process, and mild reaction conditions

Inactive Publication Date: 2011-04-13
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 serving as antitumor medicament and preparation method thereof
  • Biphenyl compound serving as antitumor medicament and preparation method thereof
  • Biphenyl compound serving as antitumor medicament and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 R in the structural formula 1 , R 2 Both are 3-chloro-4-fluoro substituted, R 3 Be the compound of diethyl, prepare by the following steps:

[0048] Preparation of 2-chloro-N-(3-chloro-4-fluorophenyl)acetamide

[0049] 1) Isovanillinization (1) Preparation of compound 2-bromoisovanillin (2) by bromination reaction

[0050] 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;

[0051] 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. ;

[0052] 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)...

Embodiment 2

[0081] Example 2 R in the structural formula 1 , R 2 Both are substituted with 4-trifluoromethyl, R 3 Be the compound of diethyl, prepare by the following steps:

[0082] 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 diformyl diethylamide (7) are the same; afterwards, in two different phenolic hydroxyl etherification processes, two phenolic hydroxyl chloroacetyl 4-trifluoromethylaniline reactions are specifically:

[0083] Dissolve 3.90g (10mmol) of compound 5,5'-dimethoxy-6,6'-dihydroxybiphenyl-2,2'-diformyldiethylamide in (7) 200mL of anhydrous acetone, add 8.30 g (60 mmol) of anhydrous potassium carbonate, stirred at room temperature for 30 minutes, then added 5.21 g (22 mmol) of 2-chloro-N-(4-trifluoromethylbenzene) acetamide, and heated to reflux at 56°C for 8 hours;

[0084] After the reaction is complete, evaporate the solvent under reduced p...

Embodiment 3

[0088] Example 3 R in the structural formula 1 , R 2 Both are 3-chloro-4-fluoro substituted, R 3 Compounds substituted with isopropyl groups are prepared by the following steps:

[0089] Steps 1) to 3) are the same as in Example 1, after which this example prepares compound 4-methoxy-3 through a two-step reaction with 4-methoxy-3-benzyloxy-2-bromobenzoic acid (4) -benzyloxy-2-bromobenzoylisopropylamide (5), specifically:

[0090] 5.04g (0.015mol) of 4-methoxy-3-benzyloxy-2-bromobenzoic acid (4) was dissolved in 50mL of dichloromethane, and 4.37mL (0.060mol) of thionyl chloride and Catalytic amount of N,N-dimethylformamide (DMF), stirred at room temperature for 3h; after the reaction was complete, the solvent was evaporated under reduced pressure, and the compound containing The residue of benzoyl chloride was dissolved in 25 mL of anhydrous dichloromethane;

[0091] Under ice-bath conditions, the obtained above solution was added dropwise to 2.58mL (0.030mmol) of isopropy...

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PUM

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Abstract

The invention discloses a biphenyl compound serving as an antitumor medicament and a preparation method thereof. The biphenyl compound has antitumor activities in vitro and in vivo, has the effects of inducing apoptosis and inhibiting proliferation on colorectal cancer cell lines, lung cancer cell lines, liver cancer cell lines, breast cancer cell lines or pancreatic cancer cell lines in vitro and has the effects of inhibiting tumors on liver cancers and colorectal cancers in vivo. The biphenyl compound can be applied to preparation of the antitumor medicament. The preparation method of the biphenyl compound has the advantages of readily available raw materials, mild reaction conditions, easily operated reaction processes and cheap and readily available 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 as an antitumor drug 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 effec...

Claims

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Application Information

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