Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors
DC Field | Value | Language |
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dc.contributor.author | Song, Yu Min | - |
dc.contributor.author | Ha, Young Mi | - |
dc.contributor.author | Kim, Jin-Ah | - |
dc.contributor.author | Chung, Ki Wung | - |
dc.contributor.author | Uehara, Yohei | - |
dc.contributor.author | Lee, Kyung Jin | - |
dc.contributor.author | Chun, Pusoon | - |
dc.contributor.author | Byun, Youngjoo | - |
dc.contributor.author | Chung, Hae Young | - |
dc.contributor.author | Moon, Hyung Ryong | - |
dc.date.accessioned | 2021-09-06T11:57:19Z | - |
dc.date.available | 2021-09-06T11:57:19Z | - |
dc.date.created | 2021-06-14 | - |
dc.date.issued | 2012-12-15 | - |
dc.identifier.issn | 0960-894X | - |
dc.identifier.uri | https://scholar.korea.ac.kr/handle/2021.sw.korea/106655 | - |
dc.description.abstract | Ten azo compounds including azo-resveratrol (5) and azo-oxyresveratrol (9) were synthesized using a modified Curtius rearrangement and diazotization followed by coupling reactions with various phenolic analogs. All synthesized compounds were evaluated for their mushroom tyrosinase inhibitory activity. Compounds 4 and 5 exhibited high tyrosinase inhibitory activity (56.25% and 72.75% at 50 mu M, respectively). The results of mushroom tyrosinase inhibition assays indicate that the 4-hydroxyphenyl moiety is essential for high inhibition and that 3,5-dihydroxyphenyl and 3,5-dimethoxyphenyl derivatives are better for tyrosinase inhibition than 2,5-dimethoxyphenyl derivatives. Particularly, introduction of hydroxyl or methoxy group into the 4-hydroxyphenyl moiety diminished or significantly reduced mushroom tryosinase inhibition. Among the synthesized azo compounds, azo-resveratrol (5) showed the most potent mushroom tyrosinase inhibition with an IC50 value of IC50 = 36.28 +/- 0.72 mu M, comparable to that of resveratrol, a well-known tyrosinase inhibitor. (C) 2012 Elsevier Ltd. All rights reserved. | - |
dc.language | English | - |
dc.language.iso | en | - |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | - |
dc.subject | TRANS-STILBENE DERIVATIVES | - |
dc.subject | ANTIOXIDANT ACTION | - |
dc.subject | IN-VITRO | - |
dc.subject | ANALOGS | - |
dc.subject | GREEN | - |
dc.title | Synthesis of novel azo-resveratrol, azo-oxyresveratrol and their derivatives as potent tyrosinase inhibitors | - |
dc.type | Article | - |
dc.contributor.affiliatedAuthor | Byun, Youngjoo | - |
dc.identifier.doi | 10.1016/j.bmcl.2012.10.050 | - |
dc.identifier.scopusid | 2-s2.0-84870242089 | - |
dc.identifier.wosid | 000311425500034 | - |
dc.identifier.bibliographicCitation | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, v.22, no.24, pp.7451 - 7455 | - |
dc.relation.isPartOf | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | - |
dc.citation.title | BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | - |
dc.citation.volume | 22 | - |
dc.citation.number | 24 | - |
dc.citation.startPage | 7451 | - |
dc.citation.endPage | 7455 | - |
dc.type.rims | ART | - |
dc.type.docType | Article | - |
dc.description.journalClass | 1 | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
dc.relation.journalResearchArea | Pharmacology & Pharmacy | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Medicinal | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Organic | - |
dc.subject.keywordPlus | TRANS-STILBENE DERIVATIVES | - |
dc.subject.keywordPlus | ANTIOXIDANT ACTION | - |
dc.subject.keywordPlus | IN-VITRO | - |
dc.subject.keywordPlus | ANALOGS | - |
dc.subject.keywordPlus | GREEN | - |
dc.subject.keywordAuthor | Azo-resveratrol | - |
dc.subject.keywordAuthor | Azo-oxyresveratrol | - |
dc.subject.keywordAuthor | Curtius rearrangement | - |
dc.subject.keywordAuthor | Anti-tyrosinase effect | - |
dc.subject.keywordAuthor | Diazotization | - |
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