Abstract
In order to develop potent skin whitening agents, we have synthesized 17 hydroxyphenyl benzyl ether compounds and tested their melanin synthesis inhibitory activity, DPPH free radical scavenging activity and tyrosinase inhibitory activity. Compounds 32, 35 and 36 possessing 4-hydroxyphenyl benzyl ether structure showed excellent inhibitory capacity with almost 50-fold than arbutin used as a reference in the inhibition test of α-MSH stimulated melanin synthesis in B-16 cells. 4-Hydroxyphenyl benzyl ether compounds also showed good antioxidant activity in the DPPH free radical scavenging test. The tyrosinase function was effectively inhibited by 3,5-dihydroxyphenyl benzyl ether analogues, especially compounds 18, 22, and 24.
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antioxidants / chemical synthesis
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Antioxidants / chemistry
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Antioxidants / pharmacology
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Benzyl Compounds / chemical synthesis
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Benzyl Compounds / chemistry
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Benzyl Compounds / pharmacology
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Biphenyl Compounds / chemistry
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Bleaching Agents / chemical synthesis*
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Bleaching Agents / chemistry
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Bleaching Agents / pharmacology*
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Ethers / chemical synthesis*
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Ethers / chemistry
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Ethers / pharmacology*
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Free Radical Scavengers / chemical synthesis
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / pharmacology
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Free Radicals / chemistry
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Humans
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Melanins / antagonists & inhibitors*
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Melanins / biosynthesis
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Melanoma, Experimental / drug therapy
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Melanoma, Experimental / metabolism
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Monophenol Monooxygenase / antagonists & inhibitors
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Phenols / chemical synthesis
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Phenols / chemistry
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Phenols / pharmacology
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Picrates / chemistry
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Skin Pigmentation / drug effects
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alpha-MSH / pharmacology
Substances
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Antioxidants
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Benzyl Compounds
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Biphenyl Compounds
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Bleaching Agents
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Ethers
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Free Radical Scavengers
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Free Radicals
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Melanins
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Phenols
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Picrates
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alpha-MSH
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1,1-diphenyl-2-picrylhydrazyl
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Monophenol Monooxygenase