Stilbene analogous compounds and their preparation methods and uses

A compound, the technology of stilbenes, applied in the field of stilbenes similar compounds and their preparation and application, can solve the problems of high price, high toxicity, fresh-keeping application restrictions, etc.

Active Publication Date: 2020-08-25
ZHEJIANG GONGSHANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most preservatives only have a single biological activity, and their fresh-keeping application is limited by their own defects, such as high price and high toxicity.

Method used

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  • Stilbene analogous compounds and their preparation methods and uses
  • Stilbene analogous compounds and their preparation methods and uses
  • Stilbene analogous compounds and their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0031] Embodiment 1-1, the preparation method of compound 1c, carry out the following steps successively:

[0032] Compound 4 was synthesized from kojic acid (3) 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) .

[0033] Compound 4: 5-benzyloxy-2-hydroxymethyl-pyran-4-one, yield 82.7%. 1 H NMR (400MHz, DMSO-d6, δppm) δ: 4.30(d, J=6.0Hz, 2H, CH 2 ),4.96(s,2H,CH 2 ), 5.67(t, J=6.0Hz, 1H, OH), 6.34(s, 1H, Py-H), 7.34-7.44(m, 5H, Ar-H), 8.17(s, 1H, Py-H) .ESI-HRMS: m / z, calculated value C 13 h 13 o 4 ([M+H] + ) 233.0808, measured value 233.0830.

[0034] A, the synthesis of compound 5

[0035] Weigh 30g (129.72mmol) of compound 4 (5-benzyloxy-2-hydroxymethyl-pyran-4-one) and dissolve it in 100mL of thionyl chloride, react at room temperature for 2h, after the reaction, suction filter, A pale yello...

Embodiment 1-2

[0050] Change the 3,5-dimethoxybenzaldehyde in Step C of Example 1-1 to 4-methoxybenzaldehyde and 3,4-dimethoxybenzaldehyde respectively, and the rest are the same as in Example 1-1 ; Thereby correspondingly obtaining compounds 1a, 1b.

[0051] The structural formula of compound 1a is:

[0052]

[0053] The structural formula of compound 1b is:

[0054]

Embodiment 2

[0055] Embodiment 2, the preparation method of compound 2h, carry out following steps successively:

[0056] Compound 4 was synthesized from kojic acid (3) 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) .

[0057] Compound 4: 5-benzyloxy-2-hydroxymethyl-pyran-4-one: yield 82.7%. 1 H NMR (400MHz, DMSO-d6, δppm) δ: 4.30(d, J=6.0Hz, 2H, CH 2 ),4.96(s,2H,CH 2 ), 5.67(t, J=6.0Hz, 1H, OH), 6.34(s, 1H, Py-H), 7.34-7.44(m, 5H, Ar-H), 8.17(s, 1H, Py-H) .ESI-HRMS: m / z, calculated value C 13 h 13 o 4 ([M+H] + ) 233.0808, measured value 233.0830.

[0058] A, the synthesis of compound 5

[0059] Weigh 30g (129.72mmol) of compound 4 (5-benzyloxy-2-hydroxymethyl-pyran-4-one) and dissolve it in 100mL of thionyl chloride, react at room temperature for 2h, and suction filter after the reaction to obtain a large...

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Abstract

The invention discloses a stilbene-like compound. The stilbene-like compound has a structure as shown in a general formula which is any one selected from the group consisting of formulas which are described in the specification. The invention also discloses a preparation method for the above-mentioned stilbene-like compound at the same time. The preparation method comprises the following steps: with kojic acid as a raw material, subjecting the kojic acid to benzyl protection and chlorination reactions, and subjecting an obtained product and triphenylphosphine to a reaction so as to obtain quaternary phosphonium salt; allowing the quaternary phosphonium salt and benzaldehyde to generate a wittig reaction; and subjecting a reaction product to deprotection with boron tribromide, or allowing the reaction product to react with aliphatic amine with different carbon chain lengths and carrying out deprotection with the boron tribromide so as to obtain the stilbene-like compound. The stilbene-like compound provided by the invention can be used as a tyrosinase inhibitor, an antibacterial agent, an antioxidant, etc.

Description

technical field [0001] The invention relates to a shrimp fresh-keeping agent with a stilbene-like structure and a preparation method thereof. The stilbene-like compound has multiple biological activities such as tyrosinase inhibitory activity, antibacterial and antioxidative properties. Background technique [0002] Shrimp is a kind of high-moisture protein food. After death, it is very susceptible to blackening and spoilage due to factors such as polyphenol oxidase and bacteria. Polyphenol oxidase (PPO) in shrimp such as tyrosinase is activated after the shrimp dies, and under aerobic conditions, the monophenols contained in shrimp are catalyzed by tyrosinase to oxidize into bisphenols Substances, and then catalyzed to generate colored quinones, and then a series of physiological and biochemical reactions occur to generate melanin, thereby causing the blackening of the shrimp body. After the shrimp body dies, the protein, amino acid and other nitrogen-containing substances...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/68C07D309/40A61K31/44A61K31/351A61P31/04A61P39/06A23B4/20A61K8/49A61Q19/02
CPCA23B4/20A23V2002/00A61K8/4926A61K8/498A61K31/351A61K31/44A61K2800/782A61P31/04A61P39/06A61Q19/02C07D213/68C07D309/40A23V2200/02A23V2200/10
Inventor 周涛陈凯
Owner ZHEJIANG GONGSHANG UNIVERSITY
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