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Preparation and application of multifunctional hydroxypyridone derivatives and hydrates thereof

A technology of hydroxypyridone and derivatives, which can be used in food ingredients as antimicrobial preservation, drug combination, skin care preparations, etc. It can solve the problems of inhibiting enzyme activity and other problems

Active Publication Date: 2019-05-21
ZHEJIANG GONGSHANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because hydroxypyridone also has a strong chelating ability to copper ions, it can inhibit the enzyme by capturing copper ions from the active center of tyrosinase, but the substituents and substitution positions on the hydroxypyridone ring inhibit it. Enzyme activity has a great influence

Method used

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  • Preparation and application of multifunctional hydroxypyridone derivatives and hydrates thereof
  • Preparation and application of multifunctional hydroxypyridone derivatives and hydrates thereof
  • Preparation and application of multifunctional hydroxypyridone derivatives and hydrates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, the synthesis of compound 1:

[0027] The route to synthesize compound 1 from kojic acid is shown in Scheme 1.

[0028]

[0029] A. Synthesis of Compound 3

[0030] It was synthesized according to the method reported in the literature (Design and synthesis of hydroxypyridinone-L-phenylalanine conjugates as potential tyrosinase inhibitors. Journal of Agricultural and Food Chemistry 2013, 61(27), 6597-6603).

[0031] B. Synthesis of Compound 4

[0032] 5-benzyloxy-2-hydroxymethylpyridin-4(1H)-one (4a): Weigh 0.129mol (30g) of compound 3 into a 500mL three-neck flask, then add 50mL of absolute ethanol, heat and stir to reflux, Subsequently, 250 mL of ammonia water (mass concentration 25-28%) was pipetted and injected therein, and the reaction progress of the system was monitored by TLC spot plate method. React at 60 ℃ for about 12h, the raw material reacted completely. After the reaction was completed, it was cooled to room temperature, and there was a...

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Abstract

The invention discloses a multifunctional hydroxypyridone derivative and a hydrate thereof. The preparation method comprises that the site 5 hydroxy of kojic acid is benzylated, the benzylated kojic acid reacts with ammonia water, the site 2 hydroxymethyl is oxidized with MnO2 to obtain an aldehyde group, the site 5 benzyl is removed with boron trichloride, reflux is performed with dilute hydrochloric acid, and evaporation is performed to obtain the mixture of the hydroxypyridone derivative and the hydrate thereof. The hydroxypyridone derivative and the hydrate thereof of the present invention can be used as the tyrosinase inhibitor.

Description

technical field [0001] The invention relates to a class of hydroxypyridone derivatives, which have multiple biological activities such as tyrosinase inhibitory activity, antibacterial and antioxidation. Background technique [0002] Tyrosinase (Tyrosinase, EC.1.14.18.1) is a copper-containing metalloenzyme widely distributed in animals, plants and microorganisms. It is a key enzyme for the synthesis of melanin in organisms. It is not only closely related to the browning of fruits and vegetables and the tanning of insect epidermis, but also has an important relationship with the occurrence and treatment of human pigmentary disorders and other diseases. At present, tyrosinase inhibitors have been used in food preservation, pesticide additives in agriculture, and whitening agents in cosmetics. Tyrosinase inhibitors play an important role in many disciplines and fields such as medicine, pharmacy, chemistry, agronomy and biology, and have attracted extensive attention from exper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/69A61K8/49A61Q19/02A61P31/04A61P39/06A23L3/3544
CPCA23V2002/00A61K8/4926A61Q19/02C07D213/69A23V2200/02A23V2200/10
Inventor 周涛赵德印
Owner ZHEJIANG GONGSHANG UNIVERSITY