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Light affinity labelling small molecular probe based on maslinic acid and preparation method thereof

A technology of small molecule probes and labeled probes, applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve problems such as unsolvable problems, and achieve the effect of promoting research and development

Inactive Publication Date: 2010-08-04
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The identification of targets is a key step in the process of drug discovery and development (Curr.Opin.Chem.Biol.2002, 6:427-433), but the current biotechnology at the gene level cannot solve which protein is targeted at a certain disease target of small molecule drugs

Method used

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  • Light affinity labelling small molecular probe based on maslinic acid and preparation method thereof
  • Light affinity labelling small molecular probe based on maslinic acid and preparation method thereof
  • Light affinity labelling small molecular probe based on maslinic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The first step is the preparation of the first compound I

[0033] Dissolve 3.0 g of maslinic acid in 50 mL of N, N-dimethylformamide, add 4.1 mL of acetic anhydride, add 10 mL of pyridine, react at room temperature for 6 hours, evaporate the solvent under reduced pressure, add 20 mL of water, and extract with dichloromethane 3 times, each Use 50 mL each time, combine the organic phases, wash with 10% dilute hydrochloric acid twice, each time using 20 mL, then wash twice with saturated sodium bicarbonate solution, each time using 20 mL, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, Silica gel column chromatography, the eluent is a mixed solvent of petroleum ether and ethyl acetate, and the ratio of the mixed solvent is petroleum ether:ethyl acetate=3:1, to obtain 3.2g of the first compound I, with a yield of 91%;

[0034] The preparation of the second step second compound II

[0035] Dissolve 2.7g of the first compound I in 50mL of di...

Embodiment 2

[0044] The first step is the preparation of the first compound I

[0045] Dissolve 3.0g of maslinic acid in 50mL of dichloromethane, add 3.5mL of acetyl chloride, add 10mL of triethylamine, react at room temperature for 6 hours, evaporate the solvent under reduced pressure, add 20mL of water, extract with ethyl acetate three times, each time with 50mL, The organic phases were combined, washed twice with 10% dilute hydrochloric acid, 20 mL each time, washed twice with 20 mL each time with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, evaporated to remove the solvent under reduced pressure, and subjected to silica gel column chromatography , the eluent is a mixed solvent of petroleum ether and ethyl acetate, and the ratio of the mixed solvent is petroleum ether: ethyl acetate=3: 1 to obtain 3.3g of the first compound I, with a yield of 94%;

[0046] The preparation of the second step second compound II

[0047] 2.7g of the first compound I was diss...

Embodiment 3

[0056] The first step is the preparation of the first compound I

[0057] Dissolve 3.0g of maslinic acid in 50mL of tetrahydrofuran, add 3.5mL of acetyl chloride, add 10mL of triethylamine, react at room temperature for 6 hours, distill off the solvent under reduced pressure, add 20mL of water, extract 3 times with 30mL of chloroform, combine the organic phases, Wash 2 times with 10% dilute hydrochloric acid, 20 mL each time, then wash 2 times with 20 mL each time with saturated sodium bicarbonate solution, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, silica gel column chromatography, eluent It is a mixed solvent of petroleum ether and ethyl acetate, the ratio of the mixed solvent is petroleum ether:ethyl acetate=3:1, and 3.0 g of the first compound I is obtained, and the yield is 85%;

[0058] The preparation of the second step second compound II

[0059] Dissolve 2.7 g of the first compound I in 40 mL of chloroform, add 10 ml of thionyl c...

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Abstract

The invention relates to a light affinity labelling small molecular probe based on maslinic acid and preparation method thereof, belonging to the technical field of organic compound and preparation thereof. Natural product maslinic acid is taken as initial raw material, compound I is obtained under the protection of acetyl, the compound I reacts with oxalyl chloride to obtain compound II, the compound II reacts with ethane diamine under single protection of Boc to obtain compound III, the compound III firstly strips Boc protecting group in HCl ethyl acetate solution and then reacts with segment IV with light affinity labelling group to obtain compound V, the compound V strips acetyl protecting group by hydrolysis with presence of alkali, so as to obtain light affinity labelling small molecular probe VI. The probe molecule can be used for researching and discovering active compound maslinic acid in vivo action target, action mode of target spot and structural information of active site and provides important information for research and development of related medicine.

Description

technical field [0001] The invention relates to a photoaffinity labeled small molecule probe based on maslinic acid and a preparation method thereof, belonging to the technical field of organic compounds and their preparation. Background technique [0002] The drug discovery process includes many stages, such as: target identification, lead compound discovery, structure optimization of small molecule compounds, preclinical and clinical trials, etc. The identification of targets is a key step in the process of drug discovery and development (Curr.Opin.Chem.Biol.2002, 6:427-433), but the current biotechnology at the gene level cannot solve which protein is targeted at a certain disease target of small molecule drugs. It is foreseeable that proteomics research carried out on the basis of genomics will lead to substantial breakthroughs in drug development, enabling life science research to achieve its ultimate goal of developing drugs for the treatment of various diseases, incl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
CPCY02P20/55
Inventor 仇文卫汤杰杨帆喻艳华邹慧龚雪萍
Owner EAST CHINA NORMAL UNIV
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