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Nitrogenous bicyclobutane derivative, and preparation method and antitumor activity thereof

A bicyclobutane and derivative technology, applied in the field of synthesis of cyclobutane skeleton compounds, can solve problems such as isomerism, low efficiency, and difficult cyclization reactions

Active Publication Date: 2021-02-23
GUANGXI UNIV FOR NATITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to free radical polymerization or cross-coupling, the [2+2] photocycloaddition reaction in solution is prone to isomerization or difficult to undergo cyclization, with many by-products and low efficiency.
[0005] For the synthesis of bicyclobutane derivatives, the original conditions for synthesizing such bicyclobutane derivatives are complicated, the yield is low, the structure is unstable, and isomers are easily produced, and the isomers of the compound will produce many unexpected Different properties, such as different configurations may produce different biological activities

Method used

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  • Nitrogenous bicyclobutane derivative, and preparation method and antitumor activity thereof
  • Nitrogenous bicyclobutane derivative, and preparation method and antitumor activity thereof
  • Nitrogenous bicyclobutane derivative, and preparation method and antitumor activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062]Preparation of 4-methyl-1,3-bis(4-vinylpyridine)benzene (ie: 4-CH3-1,3-bpeb)

[0063]Reaction step: (1) The principle of the HECK reaction, the halogenated hydrocarbon and the activated unsaturated hydrocarbon under palladium catalysis, the transfection was produced; 2.50 g (0.01 mol) of 2,4-dibromobenzene, 2.1g (0.02) Mol) 4-vinylpyridine, 0.2 g (0.00028 mol) palladium catalyst, 2.76 g (0.02 mol) of potassium anhydrous carbonate in 30 ml of DMF solvent, under 95 ° C oil bath for intra-nucleation replacement for 3 hours To generate a target product;

[0064](2) The target product was collected after the reaction was stopped, diluted with water (300 mL), and extracted with dichloromethane, combined with an organic layer, dried with anhydrous sodium sulfate, and the solvent was evaporated. Solid powder. The chemical structural formula of the product is obtainedFigure 8 Indicated.

[0065]Yield: Based on 2,4-di bromophenyl dosage, calculation 4-CH3The yield of -1,3-BPEB is 90%.

[0066]4-ch3...

Embodiment 2

[0068]Preparation of bisolenic ligand 2-methyl-1,3-di (4-vinylpyridine) benzene (ie: 2-ch3-1, 3-BPEB)

[0069]Reaction Step: (1) The principle of the reaction of the HECK reaction, the halogenated hydrocarbon and the activated unsaturated hydrocarbons were used under palladium catalysis, and the transfection was produced; 2.50 g (0.01 mol) of 2,6-dibromobromellin, 2.1g (0.02) Mol) 4-vinylpyridine, 0.2 g (0.00028 mol) palladium catalyst, 2.76 g (0.02 mol) of potassium anhydrous carbonate in 30 ml of DMF solvent, under 92 ° C oil bath for nucleophilic replacement reaction for 2.5 hours To generate a target product;

[0070](2) The target product was collected after the reaction was stopped, diluted with water (300 mL), and extracted with dichloromethane, combined with an organic layer, dried with anhydrous sodium sulfate, and the solvent was evaporated. Solid powder. The chemical structural formula of the product is obtainedFigure 9 Indicated.

[0071]Yield: Based on 2,6-di bromophenyl dosage,...

Embodiment 3

[0074]Preparation of double olefin ligand 4,6-methyl-1,3-di (4-vinylpyridine) benzene (ie: 4, 6-CH)3-1, 3-BPEB)

[0075]Reaction step: (1) The principle of the HECK reaction, the halogenated hydrocarbon and the activated unsaturated hydrocarbon under palladium catalysis, the transfection was produced; 2.50 g (0.01 mol) of 1,3-dimethyl-4, 6- Dibromobenzene, 2.0 g (0.02 mol) of 4-vinylpyridine, 0.2 g (0.00028 mol) palladium catalyst, 2.76 g (0.02 mol) of anhydrous potassium carbonate in 30 ml of DMF solvent, from 94 ° C oil bath The next nucleophilic replacement reaction for 2.8 hours, that is, the target product is generated;

[0076](2) The target product was collected after the reaction was stopped, diluted with water, extracted with dichloromethane, add activated carbon and heat the dichloromethane phase to remove impurities such as catalysts, dried with anhydrous sodium sulfate, vacuum evaporation solvent Solid powder. The chemical structural formula of the product is obtainedFigure 10...

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Abstract

The invention provides a nitrogenous bicyclobutane derivative and a preparation method and antitumor activity thereof, belonging to the technical field of synthesis of cyclobutane skeleton compounds.The nitrogenous bicyclobutane derivative is obtained by forming a coordination polymer [Cd<2>(S-1,3-bpeb)<2>(OCA)<4>]<n> from a diene-containing ligand S-1,3-bpeb and a metal atom cadmium, and then carrying out [2+2] haloaddition reaction. The invention also provides the ligand and the preparation method of the nitrogenous bicyclobutane derivative. According to the invention, it is found that whenthe ligand is 4-methyl 1,3-bis(4-vinylpyridine)benzene (4-CH3-1,3-bpeb), the synthesized nitrogenous bicyclobutane derivative (as shown in a structural formula II) has high inhibition effect on Helacells, HepG-2 cells, T-24 cells, 7402 cells and MGC80-3 cells. According to the invention, the problems of complex conditions, low yield and unstable structure in original synthesis of the bicyclobutane derivative are solve; and in addition, the preparation method of the invention has the advantages of simple production technique, low energy consumption, environment friendliness and the like.

Description

Technical field[0001]The present invention relates to the sequestration of cyclobutane skeleton compounds, and more particularly to constructing a new nitrogen-containing bicyclic butane derivative and preparation method thereof and anti-tumor activity.Background technique[0002]The polyric acid cyclobutane derivative exhibits good biological activity and medicinal value in terms of antibacterial, anti-tumor, etc., and is therefore widely used as the basic skeleton in various pharmaceutical molecules, especially for a period of time. It is increasingly widely used in synthesis of alkaloids, amino acids and non-natural and natural drug activity or biological activity. In particular, studies have shown that there is a lot of biological activity containing a cyclobutane structure in the same substituent structure than the biological activity of the cyclobutane structure. From this, the synthesis of the synthesis of the multi-nitrogen cyboxyane skeleton will play a huge role in the full ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/06C07D213/127A61P31/00A61P35/00A61K31/444
CPCC07D213/06C07D213/127A61P31/00A61P35/00
Inventor 胡飞龙王勇米艳尹显洪黄钦覃志欢梁秋蓉
Owner GUANGXI UNIV FOR NATITIES
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