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Hydroxypyridone derivatives with multiple biological activities and uses thereof

A technology of hydroxypyridone and its derivatives, which is applied in the direction of drug combination, cosmetic preparations, and chemical preservation of meat/fish. Highly stable effect

Active Publication Date: 2016-06-22
浙江欧托电气有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of kojic acid derivatives is that the structural stability is not ideal
However, kojic acid derivatives with tyrosinase inhibitory activity and antibacterial activity have not been reported yet.

Method used

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  • Hydroxypyridone derivatives with multiple biological activities and uses thereof
  • Hydroxypyridone derivatives with multiple biological activities and uses thereof
  • Hydroxypyridone derivatives with multiple biological activities and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1, the synthesis of compound 1:

[0030] The route to synthesize compound 1 from kojic acid is shown in Scheme 1.

[0031]

[0032] 5-Benzyloxy-2-hydroxymethyl-4H-pyran-4-one (4) (hereinafter referred to as compound 4) was synthesized according to the method reported in the literature (Design and synthesis of hydroxypyridinone-L-phenylalanine conjugates potential tyrosinase inhibitors. Journal of Agricultural and Food Chemistry 2013, 61 (27), 6597- 6603).

[0033] Synthesis of A, 5-benzyloxy-2-hydroxymethylpyridin-4(1H)-one (5)

[0034] Take 30 g of compound 4 and add 50 mL of ethanol, then add 250 mL of ammonia water (25-28%, weight %), reflux overnight (about 12 hours), and detect the reaction by TLC until the raw material point disappears. After the reaction was completed, cool to room temperature, the precipitate was separated out, and the precipitate was collected by filtration, then washed twice with a small amount of ether (50ml ether each time), ...

Embodiment 2

[0055] Embodiment 2, the synthesis of compound 2:

[0056] The route synthesis of compound 2 is shown in Scheme2.

[0057]

[0058] Synthesis of A, 2-aminomethyl-5-benzyloxypyridin-4(1H)-one (7)

[0059]Dissolve 10 g (43.24 mmol) of compound 5 in 215 mL of thionyl chloride, and stir at room temperature for 18 h. The reaction solution was concentrated to obtain a pale yellow solid. Then add 100mL of methanol to dissolve the solid, add 200mL of ammonia water, stir at room temperature for 2h, then heat to 40°C for 8h, and cool to room temperature. The reaction solution was concentrated to dryness, and the obtained residue was separated and purified by silica gel column chromatography (methanol:dichloromethane=1:10 volume ratio), and the purification was specifically: the silica gel column contained 300g of silica gel; Methane=1:10 (volume ratio) as washing solution; collect R f =0.35 eluent, concentrated to obtain 6.91g (30.06mmol) product 7, namely 2-aminomethyl-5-benzylo...

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PUM

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Abstract

The invention discloses a hyroxy-pyridone derivative with multiple biological activities. The hyroxy-pyridone derivative has any of the following general molecular formulas (please see the specifications), wherein in the general molecular formula 1, R refers to CH2C6H5 or CH3 or CH(CH3)2 or CH(CH3)CH2CH3 or CHCH2(CH3)2 or CH2CH2SCH3, and R' refers to an alkyl radical or a hydrocarbon oxygroup; in the general molecular formula 2, R and R' refer to CH2C6H5 or CH3 or CH(CH3)2 or CH(CH3)CH2CH3 or CHCH2(CH3)2 or CH2CH2SCH3. The invention further discloses a preparation method of the hyroxy-pyridone derivative. The hyroxy-pyridone derivative can be used as a tyrosinase inhibitor or used for retaining freshness of cosmetics or foods.

Description

technical field [0001] The invention relates to a class of hydroxypyridone derivatives, which have various biological activities such as tyrosinase inhibitory activity, antibacterial and antioxidation. Background technique [0002] Hydroxypyridone is a kind of chelating agent with strong affinity for ferric iron, which has broad application prospects in the field of medicine. Its derivative 3-hydroxy-1,2-dimethylpyridin-4-one (ie, deferiprone, Deferiprone) is an orally active iron chelating agent, which is clinically used to treat iron-excessive diseases such as thalassemia. Since iron is an element required for the growth of almost all bacteria, hydroxypyridone derivatives can limit iron absorption by removing iron from the surrounding environment of bacteria, thereby inhibiting the growth and reproduction of bacteria. In addition, hydroxypyridone also has a strong chelating ability for copper. [0003] Tyrosinase, also known as polyphenol oxidase and catechol oxidase, is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/69A61P31/04A61P39/06A61K8/49A23B4/20A61P43/00
CPCA23B4/20A61K8/4926C07D213/69
Inventor 周涛张明霞
Owner 浙江欧托电气有限公司
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