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A derivative of 3,4-dithiohydroxyhexyl methacrylate and its preparation method and application

A technology of dithiohydroxyhexyl ester and methacrylic acid, which is applied in the field of methacrylate-1-hexanol) and its preparation, can solve problems such as inconvenient operation and complex technical requirements for PDMAEMA modification, and achieve improved transfection effect of effect

Inactive Publication Date: 2021-02-05
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, the modification technology for PDMAEMA requires complicated and inconvenient operation

Method used

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  • A derivative of 3,4-dithiohydroxyhexyl methacrylate and its preparation method and application
  • A derivative of 3,4-dithiohydroxyhexyl methacrylate and its preparation method and application
  • A derivative of 3,4-dithiohydroxyhexyl methacrylate and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 30mmol of 3,4-dithiohydroxyhexyl methacrylate, 30mmol of benzyl p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve them in tetrahydrofuran, react at room temperature for 12h, and terminate the reaction. Filter with NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, a light yellow oily liquid crude product was obtained, which was purified by silica gel column chromatography to obtain an intermediate product 24mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzylcarbonic acid Ester)-1-hexanol) ester;

[0025] Add 20mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester and 20mmol N,N-dimethylaminoethylenediamine respectively in the reactor, Dissolve with tetrahydrofuran, react at room temperature for 24h, terminate the reaction, and use NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, a yellow oily liquid crude product was obtained, which was purified by silica gel chro...

Embodiment 2

[0027] Add 20mmol of 3,4-dithiohydroxyhexyl methacrylate, 30mmol of benzyl p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve them in tetrahydrofuran, react at room temperature for 6h, and terminate the reaction. Filter with NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, the light yellow oily liquid crude product was obtained, and the intermediate product 18mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzylcarbonic acid) was purified by silica gel column chromatography Ester)-1-hexanol) ester;

[0028] Add 15mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester and 20mmol N,N-dimethylaminoethylenediamine respectively in the reactor, Dissolve in tetrahydrofuran, react at room temperature for 6h, terminate the reaction, and use NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, a yellow oily liquid crude product was obtained, which was purified by silica gel column chromatog...

Embodiment 3

[0030]Add 15mmol of 3,4-dithiohydroxyhexyl methacrylate, 20mmol of benzyl p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve them in 150mL of tetrahydrofuran, react at room temperature for 12h, and terminate the reaction , filtered, with NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, the crude product of light yellow oily liquid was obtained, and the intermediate product 14mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzylcarbonic acid) was purified by silica gel column chromatography Ester)-1-hexanol) ester;

[0031] Add 10mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester and 20mmol N,N-dimethylaminoethylenediamine respectively in the reactor, Dissolve with 100mL tetrahydrofuran, react at room temperature for 12h, terminate the reaction, and use NaHCO 3 solution and saturated NaCl solution, and after rotary evaporation, a yellow oily liquid crude product was obtained, which was purified by si...

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Abstract

The present invention relates to a derivative of -3,4-dithiohydroxyhexyl methacrylate and its preparation method and application; Bian ester is a raw material, and triethylamine is an acid-binding agent, and the intermediate product methacrylate (3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester is prepared; Acrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester and N,N-dimethylaminoethylenediamine are used as raw materials, and the derivative light yellow liquid formazan is obtained by reaction (3,4-dithio-6-(2-dimethylamino-ethyl-carbamate)-1-hexanol) acrylate; polymers produced by free-radical polymerization have suitable pKa and Redox sensitivity, under redox conditions, the disulfide bond is broken to release dimethylamino, and at the same time, the loaded gene drug falls off.

Description

technical field [0001] The present invention relates to a derivative of methacrylic acid-3,4-dithiohydroxyhexyl ester and its preparation method and application, in particular to methacrylic acid (3,4-dithio-6-(2-dimethyl Amino-ethyl-carbamate)-1-hexanol) ester and a preparation method and application thereof belong to the technical field of organic compounds. Background technique [0002] Dimethylaminoethyl methacrylate (DMAEMA) is a common cationic monomer, and its polymer (PDMAEMA) can be used to deliver gene medicines. PDMAEMA is a widely studied cationic polymer. Due to the positive charge on the chain segments, PDMAEMA can effectively load various nucleic acid molecules including DNA, siRNA, etc. The ability of PDMAEMA to deliver nucleic acid molecules is mainly produced by the proton sponge effect of N,N-dimethylamino. The delivery efficiency of unmodified PDMAEMA is generally not high, and the gene delivery efficiency of PDMAEMA with different structures is also v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/12C07C319/22A61K9/51A61K47/34C08F293/00
CPCA61K9/5153C07C323/12C08F293/005C08F2438/03
Inventor 邓联东周俊辉董岸杰张建华
Owner TIANJIN UNIV