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4-[5-hydroxy-pyrone-2-ylmethyleneanimo]-3-sulfydryl-1,2,4-triazole compound and application thereof

A methylene amino, 4-HOC6H4- technology, applied in cosmetics, organic chemistry, drug combination, etc., can solve the problems of kojic acid instability and easy oxidation, and achieve the effect of simple synthesis method and easy-to-obtain materials

Inactive Publication Date: 2013-09-25
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effect of this patented chemical described by researchers is its ability to prevent tyrosine enzymes from working properly on skin cells without affecting their vital functions like photosynthesis. This makes it possible to create products with improved appearance quality such as makeup remover compositions containing specific ingredients designed specifically against these proteins.

Problems solved by technology

This patented technical problem addressed in this patents relates to developing new types of whiter teeth care compositions for reducing unwanted darkening due to exposure to solar radiation without causing damage from harmful effects like burning eyesight or hair growth issues associated therewith.

Method used

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  • 4-[5-hydroxy-pyrone-2-ylmethyleneanimo]-3-sulfydryl-1,2,4-triazole compound and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0047]Dissolve 5-hydroxy-2-formyl-4-pyrone (3 mmol) and 5-methyl-3-mercapto-4-amino-1,2,4-triazole (3.6 mmol) in 15 ml of ethanol , 2 drops of concentrated hydrochloric acid were added dropwise, and then the reaction solution was moved to an oil bath to reflux, and a yellow precipitate was produced. TLC followed the reaction. After the reaction was completed, it was cooled to room temperature. The reaction liquid was diluted with ether, filtered, and the filter residue was recrystallized to obtain yellow crystals, 5-methyl-4-[5-hydroxyl-4-pyrone-2-yl- Methylamino]-3-mercapto-1,2,4-triazole, yield: 72.8%.

[0048] 1 H NMR (DMSO-d 6 , 500 MHz) δ: 2.35(s, 3H), 7.06(s, 1H), 8.25(s, 1H), 9.66(s, 1H), 10.35(s, 1H), 13.91(s, 1H); 13 C NMR (DMSO-d 6 , 125 MHz) δ : 10.77, 117.03, 140.55, 147.50, 149.14, 151.47, 156.03, 161.42, 173.43; IR(KBr) ν : 3357, 3077, 2857, 2754, 1617, 1503, 1456, 1413, 1386, 1365, 1330, 1215, 1144, 1180, 1094, 1039, 1018, 980cm -1 ;ESI MS m / z: 253(M+H...

Embodiment 2

[0051] Dissolve 5-hydroxy-2-formyl-4-pyrone (3 mmol) and 5-trifluoromethyl-3-mercapto-4-amino-1,2,4-triazole (3.6 mmol) in 15 ml In ethanol, add 2 drops of concentrated hydrochloric acid dropwise, and then move the reaction solution to an oil bath to reflux. TLC followed the reaction. After the reaction was completed, it was cooled to room temperature. The reaction solution was diluted with ether, and a yellow precipitate was precipitated. After filtration, the filter residue was recrystallized to obtain a yellow crystal, 5-trifluoromethyl-4-[5-hydroxyl-4-pyrone -2-yl-methyleneamino]-3-mercapto-1,2,4-triazole, yield: 78.3%.

[0052] 1 H NMR (DMSO-d 6 , 500 MHz) δ: 7.08(s, 1H), 8.28(s, 1H), 9.72(s, 1H), 10.26(s, 1H), 15.02(s, 1H); 13 C NMR (DMSO-d 6 , 125 MHz) δ: 118.38, 140.83, 147.65, 154.18, 155.02, 163.93, 173.30; IR(KBr) ν: 3363, 3087,3030, 2863, 2736, 1646, 16803, 8, 15960, 149, 149 1337, 1286, 1266, 1189, 1096, 972cm -1 ; ESI MS m / z: 307(M+H) + .

[0053] Example...

Embodiment 3

[0055] Dissolve 5-hydroxy-2-formyl-4-pyrone (3 mmol) and 5-ethyl-3-mercapto-4-amino-1,2,4-triazole (3.6 mmol) in 15 ml of ethanol , 2 drops of concentrated hydrochloric acid were added dropwise, and then the reaction solution was transferred to an oil bath to reflux. TLC followed the reaction. After the reaction was completed, it was cooled to room temperature. The reaction solution was diluted with ether, and a yellow precipitate was precipitated. After filtration, the filter residue was recrystallized to obtain a yellow crystal, 5-ethyl-4-[5-hydroxyl-4-pyrone-2 -yl-methyleneamino]-3-mercapto-1,2,4-triazole, yield: 71.5%.

[0056] 1 H NMR (DMSO-d 6 , 500 MHz) δ: 1.21(t, 3H), 2.74(q, 2H), 7.04(s, 1H), 8.24(s, 1H), 9.65(s, 1H), 10.35(s, 1H), 13.93( s, 1H, OH); 13 C NMR (DMSO-d 6 , 125 mHz) Δ: 10.02, 18.20, 116.82, 140.55, 147.50, 151.45, 152.92, 156.08, 161.57, 173.40; IR (KBR) ν: 3286, 3061, 1606, 1525, 1478, 1391, 1362, 1362, 1362, 1362, 1362, 1362, 1362, 1362, 1362, 136...

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Abstract

The invention provides a novel 5-substituted-4-[5-hydroxy-pyrone-2-yl-methyleneanimo]-3-sulfydryl-1,2,4-triazole compound. The structural formula of the compound is as shown in a formula (I), wherein the substituent R is -CH3, -CF3, -CH2CH3, C6H5-, 3-CH3OC6H4, 4-CH3OC6H4-, 4-HOC6H4-, 2-CH3C6H4-, 3-CH3C6H4-, 4-CH3C6H4-, 4-C1C6H4-, 3-C1C6H4-, 4-BrC6H4-, 3-BrC6H4- or 3,5bitertiary butyl-4-hydroxy phenyl. The 5-substituted-4-[5-hydroxy-pyrone-2-yl-methyleneanimo]-3-sulfydryl-1,2,4-triazole compound provided by the invention has certain inhibitory activity for tyrosinase, and can be used for preparing skin whitening cosmetics and medicines. In addition, the synthesis method is simple, and materials are available.

Description

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Claims

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Application Information

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Owner HUNAN UNIV OF SCI & TECH
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