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Biphenyl derivative compound as well as preparation method and application thereof

A technology of derivatives and compounds, applied in the preparation of organic compounds, chemical instruments and methods, drug combinations, etc., can solve problems such as reports of unseen structures, and achieve good weight loss effects and good therapeutic effects

Inactive Publication Date: 2021-04-06
武城县人民医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention innovatively synthesizes a biphenyl derivative compound, which can be used as a regulator of transcription factors, especially a regulator of forkhead transcription protein O, and can directly regulate the above transcription factors, in order to obtain a compound that can be used to prepare transcription factors or A brand-new compound of a disease drug related to a cofactor disorder of a transcription factor, and there is no report of a related structure in the prior art

Method used

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  • Biphenyl derivative compound as well as preparation method and application thereof
  • Biphenyl derivative compound as well as preparation method and application thereof
  • Biphenyl derivative compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1, the preparation of compound 1

[0026] (1) Synthesis of 2'-methoxy-5'-nitro-[1,1':3',1'-terphenyl]-3,3"-dicarboxylic acid:

[0027]

[0028] 1,3-Dibromo-2-methoxy-5-nitrobenzene (12.18g, 0.039mol), 4-carboxyphenylboronic acid (13.61g, 0.082mol), 2M sodium carbonate solution (40.0mL) and tetrakis(triphenylphosphino)palladium (2.79g) were added into dioxane (90.0mL) solution, under the protection of nitrogen, stirred and heated to reflux for 24 hours. After cooling the reaction mixture was filtered and the solid was slurried in 6M aqueous hydrochloric acid (100 mL) for half an hour. Filtration, the filter cake was fully washed with water, and then washed with ether to obtain a dark yellow solid 2'-methoxy-5'-nitro-[1,1':3',1'-terphenyl]-3,3" - Dicarboxylic acid, 7.44 g, 48.5% yield.

[0029] 1 H-NMR (400MHz, CDCl 3 )δ: 4.16(s,3H), 7.72(t,2H), 7.85(d,2H), 8.11(s,2H), 8.26(d,2H), 8.70(s,2H). 13 C-NMR (125MHz, CDCl 3 )δ: 60.70, 124.51, 128.45, 130.29,...

Embodiment 2

[0041] The synthesis of embodiment 2, compound 2

[0042]

[0043] 5'-amino-2'-hydroxyl-[1,1':3',1"-terphenyl]-3,3"-dicarboxylic acid (10g, 0.0286mol), 2-chloro-N-(4 -Ethoxy-3-methoxyphenethyl)acetamide (23.37g, 0.086mol), sodium iodide (12.14g, 0.081mol) and potassium carbonate (18.66g, 0.135mol) were suspended in dimethylformaldehyde amide (60 mL) and stirred at 50°C for 48 hours. The solvent was concentrated under reduced pressure, the crude product was dissolved in water (80 mL), the pH was adjusted to 2.0 with hydrochloric acid, and dichloromethane (4×40 mL) was added for extraction. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure. The crude product was purified by column chromatography (eluent: EA:acetone=1:1). 5'-((2-((4-ethoxy-3-methoxyphenethyl)amino)-2-oxoethyl)amino)-2'-hydroxy-[1,1 ':3',1"-biphenyl]-3,3"-dicarboxylic acid (compound 2), 10.94g, yield 65.4%.

Embodiment 3

[0044] The synthesis of embodiment 3, compound 3

[0045]

[0046] 5'-amino-2'-hydroxy-[1,1':3',1"-terphenyl]-3,3"-dicarboxylic acid (10g, 0.0286mol), 2-chloro-N-(3 ,4-diethoxyphenethyl)acetamide (24.58g, 0.086mol), sodium iodide (12.14g, 0.081mol) and potassium carbonate (18.66g, 0.135mol) were suspended in dimethylformamide (60mL ) and stirred at 50°C for 48 hours. The solvent was concentrated under reduced pressure, the crude product was dissolved in water (80 mL), the pH was adjusted to 2.0 with hydrochloric acid, and dichloromethane (4×40 mL) was added for extraction. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to dryness under reduced pressure. The crude product was purified by column chromatography (eluent: EA:acetone=1:1). 5'-((2-((3,4-diethoxyphenethyl)amino)-2-oxoethyl)amino)-2'-hydroxy-[1,1':3 ',1"-biphenyl]-3,3"-dicarboxylic acid (compound 3), 12.24 g, yield 71.5%.

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Abstract

The invention belongs to the field of medicines, and relates to a biphenyl derivative compound as well as a preparation method and application thereof. The structural formula of the biphenyl derivative compound is shown as a formula I shown in the description. Pharmacological studies show that the compound prepared by the invention can adjust the functions of related transcription factors, especially the functions of fork transcriptional protein O, and the compound has obvious drug and therapeutic uses for malignant tumors, and has a wide application prospect, especially for treatment of malignant tumors such as hepatocellular carcinoma, breast cancer and the like, the inhibition effect is excellent.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a biphenyl derivative compound, a preparation method and its application in the preparation of a transcription factor or a transcription factor cofactor disorder-related disease medicine. Background technique [0002] Cancer is one of the leading causes of human death, accounting for about one-sixth of the total number of deaths worldwide each year. According to the global cancer report, in 2018, there were 18.1 million new cancer cases and 9.6 million deaths in the world. It has become an important disease that threatens human health. Tumor initiation is a complex process with multiple damages to the normal cellular genome. These injuries include activation of oncogenes, inactivation or deletion of tumor suppressor genes. [0003] The FOX family is called the fork-head box (fork-head box) protein, which is characterized by a DNA-binding domain with a length of 110 amino acids, which is h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C237/08C07C231/12A61P35/00
CPCA61P35/00C07C237/08
Inventor 张厚巍宫有文
Owner 武城县人民医院
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