Chloroquine photoaffinity molecular probe and preparation method and application thereof

A molecular probe, chloroquine light technology, applied in the field of chloroquine photoaffinity molecular probe and its preparation, can solve the problems of poor drug binding ability and inability to visualize enrichment and identification of target proteins

Active Publication Date: 2022-07-29
INST OF CHINESE MATERIA MEDICA CHINA ACAD OF CHINESE MEDICAL SCI
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Problems solved by technology

[0004] The present application provides a chloroquine photoaffinity molecular probe and its preparation method and application, in order to solve the problem that the target protein cannot be visualized and enriched and identified in the process of using chloroquine to treat malaria in the prior art, and at the same time Poor drug binding ability affects the use of the problem

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  • Chloroquine photoaffinity molecular probe and preparation method and application thereof
  • Chloroquine photoaffinity molecular probe and preparation method and application thereof
  • Chloroquine photoaffinity molecular probe and preparation method and application thereof

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[0025] The first embodiment of the present application discloses a method for preparing a chloroquine photoaffinity molecular probe, comprising the following steps:

[0026] S01. carry out the first nucleophilic substitution reaction with 1,4-dibromopentane and sodium azide, and then carry out hydrogenation reaction to obtain 1,4-diaminopentane;

[0027] S02. The 1,4-diaminopentane and di-tert-butyl dicarbonate are heated and refluxed, and then post-processing is performed to obtain tert-butyl (4-aminopentyl) carbamate;

[0028] S03. The tert-butyl (4-aminopentyl) carbamate, 4,7-dichloroquinoline and dimethyl sulfoxide are subjected to heating reaction, and then deprotection treatment is carried out to obtain N 4 -(7-Chloroquinolin-4-yl)pentane-1,4-diamine;

[0029] S04. Put the N 4 -(7-Chloroquinolin-4-yl)pentane-1,4-diamine reacted with acetaldehyde and then reduced to give N 4 -(7-Chloroquinolin-4-yl)-N 1 -Ethylpentane-1,4-diamine;

[0030] S05. Put the N 4 -(7-Chloro...

Embodiment 1

[0063] Chloroquine photoaffinity molecular probe and preparation method thereof

[0064] (1) Preparation of 1,4-diazidepentane 2

[0065] ;

[0066] In a 100 mL reaction flask, add sodium azide (4.3 g, 66 mmol), 1,4-dibromopentane (5.1 g, 22 mmol) and 50 mL DMF, and react overnight at 65 °C. After the reaction, 100 mL of water was added to quench, extracted with ethyl acetate (3×100 mL), the organic phase was collected, dried over anhydrous sodium sulfate, filtered, and the organic phase was concentrated in vacuo to obtain a colorless oily 1,4- Pentane diazide in 95% yield.

[0067] (2) Preparation of 1,4-pentanediamine 3

[0068] ;

[0069] In a 250mL reaction flask, add 1,4-diazidepentane (3.2 g, 21 mmol), Pd / C (400 mg) and 150 mL methanol, under H 2 Ambient, overnight reaction. After the reaction was completed, the organic phase was collected by filtration, and concentrated in vacuo to obtain 1,4-diaminopentane with a yield of 92%.

[0070] (3) Preparation of ter...

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Abstract

The invention relates to the technical field of organic chemistry, in particular to a chloroquine photoaffinity molecular probe and a preparation method and application thereof. The provided preparation method takes 1,4-dibromopentane as a raw material, and obtains N-(4-((7-chloroquine through a series of nucleophilic substitution, hydrogenation reaction, reduction reaction, amidation reaction, click reaction and the like. olin-4-yl)amino)pentyl)-N-ethyl-5-(4-((2-(3-(2-(prop-2-alkyn-1-propoxy)ethyl)-3H -Diazine-3-yl)ethoxy)methyl)-1H-1,2,3-triazol-1-yl)pentanediamine, i.e. chloroquine photoaffinity molecular probe; On the basis of , the structure was modified, and the photo-affinity diazide and alkynyl groups were introduced to obtain the probe. To achieve the purpose of visualization, enrichment and identification of target proteins, the obtained chloroquine photoaffinity molecular probe has a wide range of applications.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a chloroquine photoaffinity molecular probe and a preparation method and application thereof. Background technique [0002] Malaria is one of the deadliest infectious diseases caused by Plasmodium, widely distributed in more than 90 countries around the world, especially developing countries. It has been a serious threat to human health and social development for thousands of years. The latest World Malaria Report shows that in 2020, about 241 million people worldwide will be infected with malaria, and due to the impact of the new coronavirus pneumonia, the number of deaths has increased sharply, reaching 627,000. [0003] Drug control has always been the main method of fighting malaria. Due to its long-acting, cost-effective and well-tolerated properties, chloroquine has become the most successful antimalarial drug, playing a crucial role in the antimalarial process, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14A61K31/4706A61K47/54G01N21/64A61K31/4709A61K49/00A61P33/06
CPCC07D401/14A61K31/4706A61K47/545A61K31/4709G01N21/6428A61K49/0052A61P33/06Y02P20/55
Inventor 夏斐唐欢高鹏邱崇徐承超郭秋岩史巧莉张迎朱银华王晨王继刚
Owner INST OF CHINESE MATERIA MEDICA CHINA ACAD OF CHINESE MEDICAL SCI
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