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1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone and preparation method and application thereof

A technology of hydroxyaniline and methylene, applied in the field of medicine, can solve problems such as toxic and side effects, and achieve the effects of low production cost, good social and economic benefits, and easy availability of raw materials

Inactive Publication Date: 2020-10-27
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the existing antioxidants have good antioxidant effects, they also have some defects, and some have toxic side effects. Therefore, it is of great significance to synthesize highly efficient and low-toxic compounds with antioxidant activity through chemical reactions.

Method used

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  • 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone and preparation method and application thereof
  • 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone and preparation method and application thereof
  • 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, the structural formula is as follows:

[0033]

[0034] A preparation method of 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, comprising the following steps:

[0035] (1) adding 2-amino-4-tert-butylphenol and 2-hydroxy-1-naphthaldehyde in the reaction flask in a molar ratio of 1:1;

[0036] (2) in the reaction flask of step (1), add dehydrated alcohol, (2-amino-4-tert-butylphenol+2-hydroxy-1-naphthalene carboxaldehyde): the mass ratio of dehydrated alcohol is 1:100, in 80℃ reflux reaction for 8h;

[0037] (3) the reaction solution of step (2) is suction-filtered to obtain solid, fully washed with dehydrated alcohol and dried, and then recrystallized in dehydrated alcohol to obtain brick-red solid powder, which is 1-((5-tertiary Butyl-2-hydroxyaniline)methylene)-2-naphthone crude product;

[0038] (4) Dissolve 0.5mmol of brick red solid powder in 20ml of methanol completely, stir for 1h, filter, ...

Embodiment 2

[0048] 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, the structural formula is as follows:

[0049]

[0050] A preparation method of 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, comprising the following steps:

[0051] (1) adding 2-amino-4-tert-butylphenol and 2-hydroxy-1-naphthalene carboxaldehyde in a molar ratio of 1:1.2 to the reaction flask;

[0052] (2) Methanol was added to the reaction flask in step (1), the mass ratio of (2-amino-4-tert-butylphenol+2-hydroxy-1-naphthalenecarboxaldehyde):methanol was 1:40, and refluxed at 75°C Reaction for 10h;

[0053] (3) the reaction solution of step (2) is suction filtered to obtain solid, fully washed with dehydrated alcohol and dried, and then recrystallized in dehydrated ethanol to obtain brick-red solid powder, which is 1-((5-tertiary Butyl-2-hydroxyaniline)methylene)-2-naphthone crude product;

[0054] (4) Dissolve 0.1 mmol of brick red solid powder in 10 ml of methanol completely, stir for 2 h, ...

Embodiment 3

[0057] 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, the structural formula is as follows:

[0058]

[0059] A preparation method of 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, comprising the following steps:

[0060] (1) adding 2-amino-4-tert-butylphenol and 2-hydroxy-1-naphthaldehyde in a molar ratio of 1.2:1 to the reaction flask;

[0061] (2) Add methanol to the reaction flask of step (1), (2-amino-4-tert-butylphenol+2-hydroxy-1-naphthalenecarboxaldehyde):methanol mass ratio of 1:150, and reflux reaction at 85°C 7h;

[0062] (3) the reaction solution of step (2) is suction filtered to obtain a solid, fully washed with dehydrated alcohol and dried, and then recrystallized in dehydrated alcohol to obtain a brick-red solid powder, which is 1-((5-tertiary Butyl-2-hydroxyaniline)methylene)-2-naphthone crude product;

[0063] (4) Dissolve 0.3mmol of brick red solid powder in 15ml of methanol completely, stir for 1h, filter, and the filtrate is nat...

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Abstract

The invention discloses 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone and a preparation method and application thereof, and the compound is prepared by taking 2-hydroxy-1-naphthaldehyde and 2-amino-4-tert-butylphenol as raw materials and taking absolute ethyl alcohol or methyl alcohol as a solvent. The 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone prepared by the preparation method has a relatively strong inhibition effect on DPPH free radicals, and the inhibition effect is far higher than that of vitamin E on the DPPH free radicals. Therefore, the 1-((5-tert-butyl-2-hydroxyaniline) methylene)-2-naphthalenone has a good antioxidant effect, can be effectively used for preparing anti-aging drugs, and is an innovation in anti-aging drugs. The preparation methodhas the advantages of simple synthesis process, convenient operation, easily available raw materials, low production cost, easy industrial production, and very good social and economic benefits.

Description

technical field [0001] The invention relates to 1-((5-tert-butyl-2-hydroxyaniline)methylene)-2-naphthone, a preparation method and application thereof, and belongs to the field of medicine. Background technique [0002] Free radicals refer to chemical atoms, molecules or groups that contain unpaired electrons and are active in nature, and are biologically related free radicals, mainly including free radicals centered on N, S, O, C, H, and transition metals. Under normal circumstances, the body is rich in antioxidant enzymes (such as SOD, GSH-P), which can well remove excess free radicals in the body and keep the body healthy. If the balance is broken under pathological conditions, free radicals will Attacking other tissues and cells to obtain paired electrons can trigger diseases such as Alzheimer's disease, cardiovascular disease, coronary heart disease and tumors. The reaction of free radicals is a chain reaction. When two free radicals combine into electron pairs, the re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/18C07C221/00A61K31/135A61P39/06
CPCC07C225/18C07C221/00A61P39/06C07C2602/26C07B2200/13
Inventor 邢爱萍曾岱苑娟褚意新韩红艳王新灵张淑玲
Owner HENAN UNIV OF CHINESE MEDICINE
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