Cargando…

An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae

We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduc...

Descripción completa

Detalles Bibliográficos
Autores principales: Shih, Tzenge-Lien, Hsiao, Chih-Ang, Lin, Zi-Yu, Chen, Yau-Hung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268274/
https://www.ncbi.nlm.nih.gov/pubmed/22777189
http://dx.doi.org/10.3390/molecules17078206
_version_ 1783376249238847488
author Shih, Tzenge-Lien
Hsiao, Chih-Ang
Lin, Zi-Yu
Chen, Yau-Hung
author_facet Shih, Tzenge-Lien
Hsiao, Chih-Ang
Lin, Zi-Yu
Chen, Yau-Hung
author_sort Shih, Tzenge-Lien
collection PubMed
description We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduction. The other two analogues, 5,7-dihydroxy-3′,4′-diaminoflavone 11 and 5,7-dimethoxy-3′,4′-diaminoflavone 12, were also synthesized similarly. The above three compounds, along with flavone, were evaluated for their antioxidant and UVB-protection abilities on zebrafish larvae. The data showed that compound 10 exhibited the best result, with −102.3% of ROS-scavenging rate.
format Online
Article
Text
id pubmed-6268274
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62682742018-12-12 An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae Shih, Tzenge-Lien Hsiao, Chih-Ang Lin, Zi-Yu Chen, Yau-Hung Molecules Article We described herein a concise synthesis of 3′,4′-diaminoflavone 10. This new, three-step synthetic approach is more efficient than the conventional seven-step synthetic method. The route is shortened significantly by introducing the amino moieties early and eliminating the need for nitro group reduction. The other two analogues, 5,7-dihydroxy-3′,4′-diaminoflavone 11 and 5,7-dimethoxy-3′,4′-diaminoflavone 12, were also synthesized similarly. The above three compounds, along with flavone, were evaluated for their antioxidant and UVB-protection abilities on zebrafish larvae. The data showed that compound 10 exhibited the best result, with −102.3% of ROS-scavenging rate. MDPI 2012-07-09 /pmc/articles/PMC6268274/ /pubmed/22777189 http://dx.doi.org/10.3390/molecules17078206 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Shih, Tzenge-Lien
Hsiao, Chih-Ang
Lin, Zi-Yu
Chen, Yau-Hung
An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title_full An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title_fullStr An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title_full_unstemmed An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title_short An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae
title_sort alternative synthesis of 3′,4′-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6268274/
https://www.ncbi.nlm.nih.gov/pubmed/22777189
http://dx.doi.org/10.3390/molecules17078206
work_keys_str_mv AT shihtzengelien analternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT hsiaochihang analternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT linziyu analternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT chenyauhung analternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT shihtzengelien alternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT hsiaochihang alternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT linziyu alternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae
AT chenyauhung alternativesynthesisof34diaminoflavonestoevaluatetheirantioxidantabilityandcellapoptosisofzebrafishlarvae