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Methacrylic acid-3,4-dithio-hydrohexylacrylate derivative as well as preparation method and application thereof

A technology of dithiohydroxyhexyl ester and methacrylic acid, applied in the field of methacrylic acid-1-hexanol) ester and preparation thereof, can solve the problems of inconvenient operation, complicated technical requirements for PDMAEMA modification and the like, and achieves improved transfection efficiency. effect of effect

Inactive Publication Date: 2019-08-30
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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  • Methacrylic acid-3,4-dithio-hydrohexylacrylate derivative as well as preparation method and application thereof
  • Methacrylic acid-3,4-dithio-hydrohexylacrylate derivative as well as preparation method and application thereof
  • Methacrylic acid-3,4-dithio-hydrohexylacrylate derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 30mmol of 3,4-dithiohydroxyhexyl methacrylate, 30mmol of p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve with tetrahydrofuran, and react for 12h at room temperature to terminate the reaction. Filter with NaHCO 3 The solution and saturated NaCl solution were washed, and the crude product was obtained as a light yellow oily liquid after rotary evaporation. Purified by silica gel column, the 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 into the reactor, Dissolve in tetrahydrofuran, react at room temperature for 24h, stop the reaction, use NaHCO 3 The solution and saturated NaCl solution were washed, and the crude product was obtained as a yellow oily liquid after rotary evaporation. Purification by silica gel column was used to obtain 14mmol ...

Embodiment 2

[0027] Add 20mmol of 3,4-dithiohydroxyhexyl methacrylate, 30mmol of p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve it with tetrahydrofuran, and react at room temperature for 6 hours to terminate the reaction. Filter with NaHCO 3 The solution was washed with saturated NaCl solution, and the crude product was obtained after rotary evaporation. The crude product was purified by silica gel chromatography to obtain the intermediate product 18mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate). Ester)-1-hexanol) ester;

[0028] Add 15mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzylcarbonate)-1-hexanol) ester and 20mmol N,N-dimethylaminoethylenediamine into the reactor, Dissolve with tetrahydrofuran, react at room temperature for 6h, stop the reaction, use NaHCO 3 The solution was washed with saturated NaCl solution, and the crude product was obtained as a yellow oily liquid after rotary evaporation. Purification by silica gel column was used to ...

Embodiment 3

[0030] Add 15mmol of 3,4-dithiohydroxyhexyl methacrylate, 20mmol of p-nitrochloroformate and 30mmol of triethylamine into the reactor, dissolve with 150mL of tetrahydrofuran, and react at room temperature for 12h to terminate the reaction , Filter, use NaHCO 3 The solution and saturated NaCl solution were washed, and the crude product was obtained as a light yellow oily liquid after rotary evaporation. The intermediate product 14mmol methacrylic acid (3,4-dithio-6-(p-nitrobenzyl carbonate) was purified by silica gel 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 into the reactor, Dissolve with 100mL tetrahydrofuran, react at room temperature for 12h, stop the reaction, use NaHCO 3 The solution and saturated NaCl solution were washed, and the crude product was obtained as a yellow oily liquid after rotary evaporation, which was purified by a silica ge...

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Abstract

The invention relates to a methacrylic acid-3,4-dithio-hydrohexylacrylate derivative as well as a preparation method and an application thereof. An intermediate product methacrylic acid(3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester is prepared from methacrylic acid-3,4-dithio-hydrohexylacrylate and nitrobenzyl chloroformate as raw materials and triethylamine as an acid binding agent; methacrylic acid(3,4-dithio-6-(p-nitrobenzyl carbonate)-1-hexanol) ester and N,N-dimethylamine ethylenediamine are taken as raw materials and subjected to a reaction, and a derivative, namely, a light yellow liquid methacrylic acid(3,4-dithio-6-(2-dimethylamino-ethyl-carbamate)-1-hexanol) ester, is obtained; a polymer produced through a free radical polymerization reaction has proper pKa and oxidoreduction sensitivity, disulfide bonds break under the oxidoreduction condition, dimethylamino is released, and meanwhile, a supported gene drug falls off.

Description

Technical field [0001] The invention relates to a derivative of methacrylic acid-3,4-dithiohydroxyhexyl and its preparation method and application, in particular to methacrylic acid (3,4-dithio-6-(2-dimethyl Amino-ethyl-carbamate)-1-hexanol) ester and its preparation method and application 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 genetic drugs. PDMAEMA is a cationic polymer that has been widely studied. Due to the positive charge on the chain segment, PDMAEMA can effectively load a variety of nucleic acid molecules including DNA and siRNA. 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. The gene delivery efficiency of PDMAEMA with different structures is also very different,...

Claims

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Application Information

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Patent Type & Authority Applications(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
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