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Aromatic ring containing amine compound and preparation method and application thereof

A compound and anti-tumor drug technology, applied in the field of aromatic ring-containing amine compounds, can solve the problems of easy shedding, loose cell connection, etc., and achieve good tumor occurrence and metastasis, simple method, and the effect of inhibiting tumor occurrence and metastasis.

Inactive Publication Date: 2016-01-20
KUNMING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because breast cancer cells lose the characteristics of normal cells, the connections between cells are loose and easy to fall off

Method used

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  • Aromatic ring containing amine compound and preparation method and application thereof
  • Aromatic ring containing amine compound and preparation method and application thereof
  • Aromatic ring containing amine compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Embodiment 1: the preparation of compound I:

[0053]

[0054] 4,4-bis(4-fluorophenyl)-1-chlorobutane (compound VI-a, 0.56g, 2.0mmol) and L-phenylalanine methyl ester (VII-a, 0.72g, 4.0 mmol) was added to DMSO (10 mL) in a 25 mL single-port reaction vial with magnetic stirring, and stirred at 80° C. for 10 hours. The reactant was transferred to a 250mL separatory funnel, diluted with 150mL ethyl acetate, then washed twice with 50mL of 5% Na2CO3 aqueous solution, washed twice with 60mL of water, and finally washed once with saturated 60mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain compound I (0.97 g, 88%). 1H-NMR (CDCl3, 400MHz): 7.32~7.23(m, 5H), 7.20-7.10(m, 4H), 7.01-6.95(m, 4H), 4.08(t, J=7.7Hz, 1H), 3.64( s,3H), 3.48(m,1H), 2.94(m,2H), 2.63-2.46(m,2H), 2.03-1.96(m,3H), 1.41-1.36(m,2H). 13C-NMR (CD3OD, 100MHz): 178.3, 162.4(d, J=240Hz), 147.9, ...

Embodiment 2

[0055] Embodiment 2: the preparation of compound II:

[0056]

[0057] 4,4-bis(4-fluorophenyl)-1-chlorobutane (compound VI-a, 0.84g, 3.0mmol) and L-leucine methyl ester (VII-b, 0.87g, 6.0mmol ) was added to DMSO (20 mL) in a 50 mL single-port reaction flask with magnetic stirring, and stirred at 80° C. for 16 hours. The reactant was transferred to a 300mL separatory funnel, diluted with 200mL ethyl acetate, then washed twice with 80mL of 5% Na2CO3 aqueous solution, washed twice with 80mL of water, and finally washed once with saturated 80mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain compound II (0.95 g, 81%). 1H-NMR (CDCl3, 400MHz): 7.16-7.12(m, 4H), 6.98-6.92(m, 4H), 3.85(t, J=7.8Hz, 1H), 3.69(s, 3H), 3.22(t, J=6.9Hz,1H),2.56(m,1H),2.24(m,1H),2.03-1.98(m,2H),1.67(m,1H),1.46-1.41(m,5H),0.91(d , J=6.6Hz, 3H), 0.88(d, J=6.6Hz, 3H). 13C-NMR (CD3OD, 100MHz)...

Embodiment 3

[0058] Embodiment 3: the preparation of compound III:

[0059]

[0060] Add 4,4-bis(4-fluorophenyl)-1-chlorobutane (compound VI-a, 0.28g, 1.0mmol) and compound VII-c (0.22g, 2.0mmol) to 15mL with magnetic stirring DMSO (5 mL) in a single-port reaction flask was stirred at 80° C. for 12 hours. The reactant was transferred to a 100mL separatory funnel, diluted with 50mL ethyl acetate, then washed twice with 20mL of 5% Na2CO3 aqueous solution, washed twice with 20mL of water, and finally washed once with saturated 20mL of NaCl aqueous solution. Then the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain compound III (0.27 g, 76%). 1H-NMR (CDCl3, 400MHz): 7.76(d, J=7.3Hz, 1H), 7.21-7.11(m, 4H), 7.07-6.98(m, 4H), 6.50(m, 1H), 6.28(d, J=7.2Hz, 1H), 4.11(t, J=7.6Hz, 1H), 3.71(s, 2H), 2.98(d, J=7.3Hz, 2H), 2.61(s, 3H), 2.53-2.48( m,2H), 2.07-1.99(m,2H), 1.48-1.37(m,2H). 13C-NMR (CD3OD, 100MHz): 163.1(d,...

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Abstract

The invention discloses an aromatic ring containing amine compound and salt acceptable pharmaceutically. The aromatic ring containing amine compound has very good tumorigenesis and tumor metastasis inhibiting activity, especially has obvious inhibiting effect on prostate cancer cells and breast cancer cells, is an excellent antitumor lead compound, can be further developed into an antitumor drug, is used for treating tumor metastasis, advanced tumors, non-entity tumors and other cancers and has potential and wide application prospect the field of tumor treatment. The aromatic ring containing amine compound is prepared by adopting a halogenated part and a primary amine part to perform amine alkylation reaction in a DMSO solvent, is simple and is suitable for industrial production.

Description

[0001] This application is a divisional application of an invention patent application with the application number "201410362592.1" and the invention title "Amine Compounds Containing Aromatic Rings and Their Preparation and Application". technical field [0002] The present invention relates to amine compounds containing aromatic rings. Background technique [0003] Malignant tumors are major diseases affecting people's health. According to WHO statistics, more than 11 million cases of malignant tumors occur every year in the world, and more than 8 million people die from them. The annual incidence of tumors in developed countries is higher than 300 / 100,000. According to statistics, in the past two years, malignant tumors accounted for the first cause of death among urban residents in my country, and there were about 1.6-1.7 million new patients each year, accounting for 25.47% of fatal diseases. According to the latest "World Cancer Report" published by WHO, by 2020, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/52A61P35/00A61P35/04
CPCC07C227/18C07C229/36C07D307/52
Inventor 李维莉马银海鞠海东黄文忠
Owner KUNMING UNIV
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