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8-aminoquinoline derivative and preparation and application thereof

A technology for aminoquinoline and derivatives, which is applied in the field of 8-aminoquinoline derivatives, and can solve problems such as high cost, complicated preparation, and lack of modification methods

Active Publication Date: 2017-01-25
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are some methods for modifying 8-aminoquinoline drugs by C-H activation technology, their preparation is relatively complicated and the cost is high, and a simple and effective modification method is lacking.

Method used

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  • 8-aminoquinoline derivative and preparation and application thereof
  • 8-aminoquinoline derivative and preparation and application thereof
  • 8-aminoquinoline derivative and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: Preparation N-(5-azidoquinoline-8-amino) benzamide

[0050]

[0051] Add 0.1mmol of N-(quinoline-8amino)benzamide (II-1) to 5ml of N,N-dimethylformamide and 5ml of deionized water to make a mixed solution of 10ml, and add 0.3mmol of azide to it Sodium chloride, copper acetate 0.03mmol, 0.3mmol potassium persulfate, 0.1mmol DBU, 0.1mmol TBAB, react at 40°C for 12 hours, after the reaction, add saturated NaCl aqueous solution to the reaction solution, extract with dichloromethane, take the organic layer through Dry over anhydrous magnesium sulfate, filter, evaporate under reduced pressure at 60°C to remove the solvent, and obtain the crude compound represented by the formula (I-1). The crude compound represented by formula (I-1) was subjected to silica gel column chromatography, with a solution of ethyl acetate and petroleum ether at a volume ratio of 1:5 as the mobile phase, and the eluent with an Rf value of 0.3-0.5 was collected by TLC tracking , the ...

Embodiment 2

[0053] Embodiment 2: Preparation of N-(5-azidoquinoline-8-amino)-3-methyl-benzamide

[0054]

[0055] Add 0.1mmol N-(quinoline-8 amino)-3-methylbenzamide (II-2) to 5ml of N,N-dimethylformamide and 5ml of deionized water to make a mixed solution of 10ml, add 0.3mmol sodium azide, 0.03mmol copper acetate, 0.3mmol potassium persulfate, 0.1mmol DBU, 0.1mmol TBAB, react at 40°C for 12 hours, after the reaction, add saturated NaCl aqueous solution to the reaction solution, extract with dichloromethane, The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure at 60°C to remove the solvent to obtain the crude compound of the formula (I-2), and the crude compound of the formula (I-2) was subjected to silica gel column chromatography , using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:10 as the mobile phase, TLC tracked and collected the eluent with an Rf value of 0.3-0.5, and collected the eluent obtai...

Embodiment 3

[0057] Embodiment 3: Preparation of N-(5-azidoquinoline-8-amino)-4-methyl-benzamide

[0058]

[0059]Add 0.1mmol N-(5-quinoline-8-amino)-4-methyl-benzamide (II-3) to 5ml of N,N-dimethylformamide and 5ml of deionized water to make a mixed solution of 10ml , add 0.3mmol sodium azide, 0.03mmol copper acetate, 0.3mmol potassium persulfate, 0.1mmol DBU, 0.1mmol TBAB, and react at 40°C for 12 hours. Extract with methyl chloride, take the organic layer, dry it with anhydrous magnesium sulfate, filter, evaporate under reduced pressure at 60°C to remove the solvent, and obtain the crude compound shown in the formula (I-3), and carry out the crude product of the compound shown in the formula (I-3) Column chromatography, using a solution of ethyl acetate and petroleum ether with a volume ratio of 1:5 as the mobile phase, TLC tracking and collecting the eluent with an Rf value of 0.3-0.5, and the collected eluent was removed from the solvent under reduced pressure. After drying, 20 mg...

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Abstract

The invention discloses an 8-aminoquinoline derivative, preparation thereof and application thereof to preparation of anti-malaria and anti-tumor drugs. In formula (I), R1 refers to phenyl, substituted phenyl, C5-C6 aromatic ring, C1-C10 alkyl, C1-C10 alkoxy or C1-C10 substituted alkyl, a substituting group of the substituted phenyl refers to methyl, chlorine, nitryl, fluorine or methoxyl, the substituted alkyl refers to leucine-5-azide quinoline, R2 refers to H or methyl, R3 refers to -N3, -NH2 or (formula), and R4 refers to phenyl, C5-C6 aromatic ring or C1-C10 alkyl. The 8-aminoquinoline derivative and preparation and application thereof have the advantages that simplicity, high efficiency and rapidity in operation process are achieved, raw materials are easily available, the anti-malaria activity (IC50<0.1 micrometer) of the 8-aminoquinoline derivative is improved by more than 6 times than that (IC50=0.64 micrometer) of 8-aminoquinoline, and the anti-tumor activity thereof is improved by more than 10 times than that of 8-aminoquinoline.

Description

[0001] (1) Technical field [0002] The invention relates to an 8-aminoquinoline derivative, in particular to an 8-aminoquinoline derivative and its preparation and application. [0003] (2) Background technology [0004] Malaria (malaria) is an infectious disease that causes malaria parasites to parasitize the human body through the bite or blood transmission of malaria parasites. According to the World Health Organization, malaria is the third largest infectious disease in the world after AIDS and tuberculosis. Malaria has the characteristics of high morbidity and high lethality, and has brought great disasters to people in history. According to statistics, nearly 500 million people are infected with malaria every year in the world, resulting in more than one million deaths. Malaria is mainly prevalent in third world countries, especially poor countries in Central Africa and South Asia. It brought great disaster and pain to the local people. Currently, the main antimalaria...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/40C07D401/04A61P35/00
CPCC07D215/40C07D401/04Y02A50/30
Inventor 朱勍窦言东
Owner ZHEJIANG UNIV OF TECH
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