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Hydroxypyridinone derivative of aza-chalcone structure, preparation method and application

A technology of hydroxypyridone and heterochalcone, which is applied in the direction of medical preparations containing active ingredients, skin care preparations, applications, etc., can solve the problems of high price and high toxicity, and achieve good monophenolase inhibitory activity Effect

Active Publication Date: 2019-07-05
ZHEJIANG GONGSHANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many inhibitors have been greatly limited in application due to their own defects, such as high price and high toxicity.

Method used

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  • Hydroxypyridinone derivative of aza-chalcone structure, preparation method and application
  • Hydroxypyridinone derivative of aza-chalcone structure, preparation method and application
  • Hydroxypyridinone derivative of aza-chalcone structure, preparation method and application

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Embodiment Construction

[0024] The present invention is further described below in conjunction with specific embodiment, but protection scope of the present invention is not limited thereto:

[0025] The route for synthesizing compound 1(a-o) from Kojic Acid (Kojic Acid) is shown in Scheme 1.

[0026]

[0027]

[0028]

[0029] Scheme 1

[0030] Compound 2 was synthesized from kojic acid 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] A, the synthesis of compound 3

[0032] 1), the synthesis of compound 3a

[0033] Add 10 g of compound 2 into 17 mL of absolute ethanol, heat to reflux in an oil bath while stirring, then inject 83 mL of ammonia water (mass concentration 25-28%) into it, react overnight at 60°C, and monitor the reaction progress by TLC. After the reaction was completed (reaction time was 12 ...

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Abstract

The invention discloses a hydroxypyridinone derivative of an aza-chalcone structure. According to a structural formula I, X is O and N-CnH2N+1(n=0-12); R2 is H, 4-F, 2-OH, 4-OCH3, 3,4-di-OCH3 and 3,4-di-OH. The invention further discloses a preparation method and application of the hydroxypyridinone derivative of the aza-chalcone structure at the same time. The hydroxypyridinone derivative can betaken as a tyrosinase inhibitor and used for freshness keeping of cosmetics or foods.

Description

technical field [0001] The invention relates to a class of tyrosinase inhibitors and a preparation method thereof. The compounds are hydroxypyridone derivatives with an azachalcone structure. Background technique [0002] Tyrosinase (Tyrosinase, EC1.14.18.1), also known as polyphenol oxidase and catechol oxidase, is a multi-subunit copper-containing oxidoreductase with complex structure. It is widely found in animals and plants such as apples, mushrooms, and the human body, as well as in microorganisms, especially molds. Tyrosinase is the key enzyme and rate-limiting enzyme for melanin synthesis in organisms. It not only determines the rate of melanin synthesis, but also marks the differentiation and maturation of melanocytes. Tyrosinase exists in various levels of biological systems. It is the main enzyme that causes browning of fruits, vegetables and aquatic products. It is closely related to the tanning and development of insects, and is also closely related to human pig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/69A23L3/3544A61K8/49A61Q19/02
CPCA23L3/3544A61K8/4926A61K2800/524A61K2800/782A61Q19/02C07D213/69
Inventor 周涛拉图尔·拉维特吉·辛格陈凯
Owner ZHEJIANG GONGSHANG UNIVERSITY
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