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1,8-naphthalimide derivative as well as synthesis method and application thereof

A synthesis method and product technology, applied in the field of medicine, can solve the problems that have not been seen before, and achieve good medicinal value and remarkable anti-tumor activity in vitro

Inactive Publication Date: 2015-04-29
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no 1,8-naphthalimide derivative N-(3,4-methylenedioxyphenethyl)-4-(3-N,N-dimethylamino)propylamino-1 , 8-Naphthalimide and related reports on its synthesis and application

Method used

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  • 1,8-naphthalimide derivative as well as synthesis method and application thereof
  • 1,8-naphthalimide derivative as well as synthesis method and application thereof
  • 1,8-naphthalimide derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] 1) Add 2.77g of 4-bromo-1,8-naphthalene dicarboxylic anhydride (10mmol) into 150ml of ethanol, stir to form a suspension, then add 1.65g of 3,4-methylenedioxyphenethylamine (10mmol ) was added to the suspension, heated to reflux for 8 hours. After the reaction was completed, it was cooled, filtered, and the filter cake was recrystallized with dichloromethane to obtain 3.81 g of an intermediate product with a yield of 90%.

[0030] 2) Dissolve 4.23g of the intermediate product (10mmol) in 50mL of DMSO, add 1.02g of N-dimethyl-1,3-diaminopropane (10mmol), and heat to 135°C for 8 hours. After the reaction was completed, the reactant was put into ice water, and the yellow solid was filtered out, which was the crude product.

[0031] 3) The crude product was purified by silica gel column chromatography (elution solvent: dichloromethane / methanol=1:20, volume ratio) to obtain 2.23 g of a yellow solid product with a yield of 50%.

[0032] The resulting yellow solid product is...

Embodiment 2

[0040] 1) Add 2.77g of 4-bromo-1,8-naphthalic anhydride (10mmol) into 150ml of methanol, stir to form a suspension, then add 1.65g of 3,4-methylenedioxyphenethylamine (10mmol ) was added to the suspension, heated to reflux for 8 hours. After the reaction was completed, it was cooled and filtered, and the filter cake was recrystallized twice with dichloromethane to obtain 3.0 g of an intermediate product with a yield of 71%.

[0041] 2) Dissolve 4.23g of the intermediate product (10mmol) in 50mL of DMSO, add 1.02g of N-dimethyl-1,3-diaminopropane (10mmol), and heat to 150°C for 8 hours. After the reaction was completed, the reactant was put into ice water, and the yellow solid was filtered out, which was the crude product.

[0042] 3) Purify the crude product by silica gel column chromatography (elution solvent is dichloromethane / methanol=1:50, volume ratio) to obtain N-(3,4-methylenedioxyphenethyl)-4-(3- N,N-dimethylamino)propylamino-1,8-naphthalimide 2.14g, yield 48%.

Embodiment 3

[0044] 1) Add 2.77g of 4-bromo-1,8-naphthalene dicarboxylic anhydride (10mmol) into 150ml of ethanol, stir to form a suspension, then add 1.65g of 3,4-methylenedioxyphenethylamine (10mmol ) was added to the suspension, heated to reflux for 10 hours. After the reaction was completed, it was cooled and filtered, and the filter cake was recrystallized with chloroform to obtain 3.81 g of an intermediate product with a yield of 90%.

[0045] 2) Dissolve 4.23g of the intermediate product (10mmol) in 50ml of ethylene glycol methyl ether, add 1.02g of N-dimethyl-1,3-diaminopropane (10mmol), and heat to 110°C for 8 hours. After the reaction was completed, the reactant was put into ice water, and the yellow solid was filtered out, which was the crude product.

[0046] 3) Purify the crude product by silica gel column chromatography (elution solvent is dichloromethane / methanol=1:100, volume ratio) to obtain N-(3,4-methylenedioxyphenethyl)-4-(3- N,N-dimethylamino)propylamino-1,8-naphthal...

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Abstract

The invention discloses a 1,8-naphthalimide derivative as well as a synthesis method and an application thereof. The derivative is N-(3,4-methylene dioxophenethyl)-4-(3-N,N-dimethylamino)propylamino-1,8-naphthalimide; and the compound is prepared by taking 4-bromo-1,8-naphthalic anhydride as a raw material which sequentially reacts with 3,4-methylene dioxophenylethylamine and N,N-dimethyl-1,3-diaminopropane. The synthesis method is simple and easy to control. The applicant observes the proliferation inhibition activity of the 1,8-naphthalimide derivative on 9 human tumor cell strains and two normal cell strains, and the results indicate that the in-vitro antitumor activity is remarkable and the 1,8-naphthalimide derivative has relatively good potential medicinal value and is expected to be applied to the preparation of various anti-tumor drugs. The chemical structural formula of the compound disclosed by the invention is shown by the formula (I).

Description

technical field [0001] The invention relates to the field of medical technology, in particular to a 1,8-naphthalimide derivative and its synthesis method and application. Background technique [0002] Naphthalimide derivatives are a class of excellent chromophores, most of which are used in the form of fluorescent molecular probes. Due to the unique planar rigid structure of naphthalimide derivatives, they have a strong ability to intercalate DNA, and have been receiving much attention in the field of anti-tumor drug development in the past 30 years. Several naphthalimide derivatives such as anifext, mitonaftide, ilinefade and binaphate have been studied clinically. [0003] In recent years, there are still many reports on naphthalimide derivatives as anti-tumor compounds. Among them, Kamal in India, Lee in the United States and Tarasova's research team successfully synthesized pyrrolobenzodiazepine (Bioorg.Med.Chem.Lett.2002121933-1935 ), polyamide hairpin, imidazoacridin...

Claims

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Application Information

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IPC IPC(8): C07D405/06A61P35/00
CPCC07D405/06
Inventor 张国海彭艳仲辉卢幸安运锋
Owner GUANGXI NORMAL UNIV
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