5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-hydroxybenzylamino-1,2,4-triazole compounds and their uses

A technology of hydroxybenzylamino and pyrone, which can be used in cosmetics, organic chemistry, drug combination, etc., can solve the problems of unsatisfactory whitening effect and no cytotoxicity.

Active Publication Date: 2017-12-19
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Arbutin, a glycoside derivative of hydroquinone, was developed as a commercial product because it is not cytotoxic at active doses, but its whitening effect is not satisfactory

Method used

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  • 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-hydroxybenzylamino-1,2,4-triazole compounds and their uses
  • 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-hydroxybenzylamino-1,2,4-triazole compounds and their uses
  • 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-hydroxybenzylamino-1,2,4-triazole compounds and their uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] Example 1: Synthesis of 3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-(2-hydroxybenzylamino)-1,2,4-triazole.

[0145] First, dissolve 2-hydroxybenzaldehyde (2.0 mmol) and 3-mercapto-4-amino-1,2,4-triazole (2.2 mmol) in 5 ml of absolute ethanol, add p-toluenesulfonic acid (0.4 mmol), Reflux at a temperature of 80°C. The reaction was tracked by TLC. After the reaction was completed, it was cooled to room temperature, and about 50 ml of distilled water was added, and a tan solid was precipitated. Filter, wash the filter residue with distilled water for 2 to 3 times, and dry to obtain Schiff base 4-(2-hydroxybenzylideneamino)-3-mercapto-1,2,4-triazole; weigh the above Schiff base (1.5 mmol) into a reaction flask, dissolved with an appropriate amount of methanol, and added NaBH in batches under ice-bath conditions 4 (2.0 mmol), after the addition, the reaction was continued for about 6 min under ice bath. TLC followed the reaction. After the reaction was over, about 50 ml of ...

Embodiment 2

[0147] Example 2: 5-methyl-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-(2-hydroxybenzylamino)-1,2,4-triazole Synthesis.

[0148] First, dissolve 2-hydroxybenzaldehyde (2.0 mmol) and 5-methyl-3-mercapto-4-amino-1,2,4-triazole (2.2 mmol) in 5 ml of absolute ethanol, add p-toluenesulfonate Acid (0.4 mmol), reflux at 80°C. The reaction was tracked by TLC. After the reaction was completed, it was cooled to room temperature, and about 50 ml of distilled water was added, and a tan solid was precipitated. Filter, wash the filter residue with distilled water 2 to 3 times, and dry to obtain Schiff base 5-methyl-4-(2-hydroxybenzylideneamino)-3-mercapto-1,2,4-triazole; weigh the above Schiff's base (1.5 mmol) was put into a reaction flask, dissolved with an appropriate amount of methanol, and NaBH was added in batches under ice-bath conditions. 4 (2.0 mmol), after the addition, the reaction was continued for about 6 min under ice bath. TLC followed the reaction. After the reaction was o...

Embodiment 3

[0150] Example 3: 5-methyl-3-[5-hydroxy-4-pyrone-2-yl-methylthio]-4-(3-hydroxybenzylamino)-1,2,4-triazole Synthesis.

[0151] First dissolve 3-hydroxybenzaldehyde (2.0 mmol) and 5-methyl-3-mercapto-4-amino-1,2,4-triazole (2.2 mmol) in 5 ml of absolute ethanol, add p-toluenesulfonate Acid (0.4 mmol), reflux at 80°C. The reaction was tracked by TLC. After the reaction was completed, it was cooled to room temperature, and about 50 ml of distilled water was added, and a tan solid was precipitated. Filter, wash the filter residue with distilled water 2 to 3 times, and dry to obtain Schiff base 5-methyl-4-(3-hydroxybenzylideneamino)-3-mercapto-1,2,4-triazole; weigh the above Schiff's base (1.5 mmol) was put into a reaction flask, dissolved with an appropriate amount of methanol, and NaBH was added in batches under ice-bath conditions. 4 (2.0 mmol), after the addition, the reaction was continued for about 6 min under ice bath. TLC followed the reaction. After the reaction was ov...

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Abstract

The invention provides novel 5-substituted-3-[5-hydroxyl-4-pyrone-2-yl-methylthio]-4- hydroxybenzyl-methylamino-1,2,4-triazole compounds represented in a formula (I). In the formula (I), a substituent R1 is H, -CH3, -CH2CH3, C6H5-, 2-CH3C6H4-, 3-CH3C6H4-, 4-CH3C6H4-, 4-CH3OC6H4-, 2-ClC6H4-, 3-ClC6H4- and 4-ClC6H4-, and R2 is 2-OH, 3-OH, 4-OH, 2,3-di-OH, 2,4-di-OH and 3,4-di-OH. The 5-substituted-3-[5-hydroxyl-4-pyrone-2-yl-methylthio]-4- hydroxybenzyl-methylamino-1,2,4-triazole compounds have certain inhibitory activity on tyrosinase, a synthetic method of the compounds is simple, and materials are easy to obtain; the compounds can be used for preparing cosmetics or drugs with the melanogenesis inhibiting or skin whitening function.

Description

technical field [0001] The present invention relates to a class of novel 5-substituted-3-[5-hydroxyl-4-pyrone-2-yl-methylthio]-4-hydroxybenzylamino-1,2,4-triazole compounds , is a new tyrosinase inhibitor, used as a melanin inhibitor or whitening agent in the fields of medicine, food, and daily chemical industry. Background technique [0002] Studies have shown that hyperpigmentation is caused by ultraviolet rays activating melanin-producing enzymes in melanocytes in the epidermis to produce pigments. In the process of melanin production, tyrosinase is a key enzyme, which converts tyrosine into dopa and dopaquinone, and then the dopaquinone is polymerized into macromolecular melanin through non-enzymatic oxidation[1]. Therefore, by inhibiting the catalytic activity of tyrosinase, melanin production can be limited, thereby improving skin pigmentation. [0003] Effective melanin inhibitors and whitening agents have a broad consumer market. At present, many tyrosinase inhibit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12A61K31/4196A61K8/49A61P17/00A61Q19/02
CPCA61K8/498A61K2800/10A61Q19/02C07D405/12
Inventor 谢文林张金改余秋艳何晶晶李芯蕊骆春香李尚儒柳建斌
Owner HUNAN UNIV OF SCI & TECH
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