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Water-soluble cationic polyamidine and preparation method thereof

A technology of water-soluble cationic polyamidine, which is applied in the field of water-soluble cationic polyamidine and its preparation, can solve the problems of unfriendly environment and achieve the effects of environmental friendliness, simple operation and improved biocompatibility

Active Publication Date: 2021-10-26
JIANGSU ZHONGLI GRP CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although various methods for the preparation of amidines have been reported, most of them are based on environmentally unfriendly isonitriles, nitriles, azides, or transition metals such as Pd.

Method used

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  • Water-soluble cationic polyamidine and preparation method thereof
  • Water-soluble cationic polyamidine and preparation method thereof
  • Water-soluble cationic polyamidine and preparation method thereof

Examples

Experimental program
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preparation example Construction

[0033] The present invention provides a method for preparing water-soluble cationic polyproducts, including:

[0034] S1, in an organic solvent, dinitrobenzene and N, N-dibromobethalate, and a mid-secondary amine reaction to obtain a tert-butoxycarbonyl substituted polyhydration, the reaction formula is as follows:

[0035]

[0036] S2, remove the tert-butoxycarbonyl group to obtain a water-soluble cationic polyproduct.

[0037] Among them, R 1 R 2 Alkyl or aryl, R 1 R 2 Similarly or different, the specific structure of R1 and R2, this is not one by one, R 1 R 2 Depending on the specific structure of the mid-second amine monomer.

[0038] The reaction temperature was 40 ° C to 80 ° C, and the reaction time was 6 H-72H. The molar ratio of dinitrobenylbenzene and N, N-dibrominine and midupermide is 1: 2: 0.5-2, and the concentration of 0.01 to 10 mol / L of dinitrobenzene. The organic solvent is chloroform or methanol, but it is not limited thereto, and may be other organic solven...

Embodiment 1

[0056] Double primary amine monomer selection piperazine: accurately weigh dinitrobenzene (22 mg, 0.1 mmol) and N, N-dibrominamate (54.6 mg, 0.2 mmol) in the reaction bottle, and accurate The addition of potassium phosphate (106.3 mg, 0.4 mmol) was added to the reaction flask, and then 0.5 mL-2 mL of chloroform was added to the reaction bottle and heated to 40 ° C to 70 ° C, and then mixed with piperazine (8.4 mg, 0.1 mmol), the maintenance temperature was 40 ° C to 70 ° C and stirred for 6-72 h, and the reaction was stopped. The crude product was dissolved in anhydrous methanol by sinking from an unhautus to anhydrous methanol, and the dialysis was dialyzed in anhydrous methanol (the dialysis bag was quantified by 1000 Da), and the tenthoacarbonyl substituted polymer was concentrated.

[0057] The above polymer (21 mg, 0.05 mmol) is accurately weighed in an appropriate amount of chloroform or dichloromethane, and the reaction bottle is placed in a low temperature reactor and the ...

Embodiment 2

[0059] Double primary amine monomer selected n, N-dimethyl-1,3-ethylenediamine: accurate weight dinomide (22 mg, 0.1 mmol) and N, N-dibromoamate (54.6 Mg, 0.2 mmol) was placed in the reaction flask, accurately weighed potassium phosphate (106.3 mg, 0.4 mmol) to add the reaction bottle, then weighed 0.5 mL-2 mL of chloroform and heated to 40 ° C to 70 ° C, After stirring, N, N-dimethyl-1,3-ethylenediamine monomer (10.7 μL, 0.1 mmol) was added, and the maintenance temperature was 40 ° C to 70 ° C and stirred for 6-72 h, and the reaction was stopped. The crude product was dissolved in anhydrous methanol by sinking from an unhautus to anhydrous methanol, and the dialysis was dialyzed in anhydrous methanol (the dialysis bag was quantified by 1000 Da), and the tenthoacarbonyl substituted polymer was concentrated. The nuclear magnetomy of the obtained tert-butoxycarbonyl substituted polymer is figure 2 Indicated.

[0060] The above polymer (21.5 mg, 0.05 mmol) was accurately weighed in a...

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Abstract

The invention relates to a preparation method of water-soluble cationic polyamidine, which comprises the following steps that S1, in an organic solvent, dinitrovinyl benzene, N, N-dibromocarbamate and bis-secondary amine react to prepare t-butyloxycarbonyl substituted polyamidine, the reaction temperature is 40-80 DEG C, and the reaction time is 6-72 hours; the molar ratio of the dinitrovinyl benzene to the N, N-dibromocarbamate to the bis-secondary amine is 1: 2: (0.5-2), and the concentration of the dinitrovinyl benzene is 0.01-10 mol / L; and S2, the t-butyloxycarboryl is removed to obtain the water-soluble cationic polyamidine. The water-soluble cationic polyamidine is prepared by using dinitrovinyl benzene, N, N-dibromocarbamate and bis-secondary amine as raw materials through reaction, the preparation method is simple to operate, mild in reaction condition, environment-friendly and free of a metal catalyst, the prepared water-soluble cationic polyamidine has water solubility, the biocompatibility is improved, and the gene can be effectively entrapped.

Description

Technical field [0001] The present invention relates to a water-soluble cationic polyhydration and a preparation method thereof, belonging to the field of organic synthesis. Background technique [0002] Multicomponent Reaction, MCR) refers to three or more substrates, and has a solution to synthesize complex compounds by a pot, which has a complex structural compound, simple and convenient, high economics, and productivity. Good advantage, rapid development in the field of biology, medicine and chemistry. MulticomponentPolyMerization, MCP is a new type of polymerization method developed based on multi-component reaction, and has a simple and efficient synthetic structure with a pot in a pot to have a mild, atomic economy, operation. Simple, structural diversity and other advantages. MCP broadens the versatility of the polymer by participating in three or more monomers compared to the conventional method of using two monomer polycondensation. [0003] Polyproduct is a polymer con...

Claims

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Application Information

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IPC IPC(8): C08G73/00
CPCC08G73/00Y02P20/55
Inventor 陈新祥郑玉斌张跃宗宋汪泽刘焱鑫王达伟王思元詹雪琦黄钰
Owner JIANGSU ZHONGLI GRP CO LTD
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