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Tyrosinase inhibitor and its preparation method and use

A technology of tyrosinase and inhibitors, which is applied in the field of hydroxypyridone derivatives, can solve the problems of inhibiting enzyme activity and other problems, and achieve good stability and high stability

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

Due to its strong chelating ability to copper ions, hydroxypyridone can inhibit the enzyme by capturing the copper ions in the active center of tyrosinase, but the substituents and substitution positions on the hydroxypyridone ring inhibit the enzyme. activity has a great influence

Method used

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  • Tyrosinase inhibitor and its preparation method and use
  • Tyrosinase inhibitor and its preparation method and use
  • Tyrosinase inhibitor and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, the synthesis of compound 1a-1f:

[0025] The routes for the synthesis of compounds 1a-1f from kojic acid are shown in Scheme 1.

[0026]

[0027] Compound 3 was synthesized from kojic acid (2) 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) .

[0028] A, the synthesis of compound 4

[0029] 1), the synthesis of compound 4a-4c

[0030] Take 10 g of compound 3 and add 17 mL of absolute ethanol, heat and reflux in an oil bath while stirring, then measure 83 mL of ammonia water (mass concentration 25-28%) into it, react at 60°C overnight, and monitor the reaction progress by TLC. After the reaction was completed (reaction time was 12 hours), it was cooled to room temperature and left to stand. The precipitate was collected by filtration, washed twice with a small amount of ether,...

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Abstract

The present invention discloses an oxime ether group-containing hydroxypyridone derivative having tyrosinase inhibition activity. The preparation method comprises that the site 5 hydroxy of kojic acid is benzylated, the benzylated kojic acid reacts with ammonia water or fatty amine containing different carbon chain lengths, the site 2 hydroxymethyl is subjected to selective oxidation with active manganese dioxide to obtain a pyridone derivative having an aldehyde group at site 2, O-alkyl hydroxyl amine and the pyridone derivative having the aldehyde group at site 2 are subjected to a condensation reaction, and the benzyl group is removed with hydrochloric acid to obtain the oxime ether group-containing hydroxypyridone derivative. The oxime ether group-containing hydroxypyridone derivative of the present invention can be used as the tyrosinase inhibitor.

Description

technical field [0001] The invention relates to a class of tyrosinase inhibitors and a preparation method thereof. The compound is a hydroxypyridone derivative containing an oxime ether group, that is, a hydroxypyridine containing an oxime ether group with tyrosinase inhibitory activity Ketone derivatives. Background technique [0002] Tyrosinase (Tyrosinase, EC.1.14.18.1) is a ketone-containing metalloenzyme, which has both monophenolase and diphenolase biological activities, and is widely distributed in animals, plants and microorganisms. It is often called tyrosinase in animals and microorganisms, and polyphenol oxidase in plants. According to current research, tyrosinase is a key enzyme involved in melanin metabolism in organisms, which not only determines the rate of melanin synthesis, but also marks the degree of melanocyte differentiation and maturity. In addition, it also has important physiological functions in organisms, in addition to forming protective melanin ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/69A61K8/49A61Q19/00A23L3/3544
CPCA61K8/4926A61K2800/10A61K2800/524A61K2800/782A61Q19/00C07D213/69
Inventor 周涛邵乐乐
Owner ZHEJIANG GONGSHANG UNIVERSITY
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