An alternative synthesis of 3?,4?-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae

Tzenge Lien Shih; Chih Ang Hsiao; Zi Yu Lin; Yau Hung Chen

doi:10.3390/molecules17078206

An alternative synthesis of 3?,4?-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae

Tzenge Lien Shih^*, Chih Ang Hsiao, Zi Yu Lin, Yau Hung Chen

^*Corresponding author for this work

Tamkang University

Research output: Contribution to journal › Journal Article › peer-review

4 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	8206-8216
Number of pages	11
Journal	Molecules
Volume	17
Issue number	7
DOIs	https://doi.org/10.3390/molecules17078206
State	Published - 07 2012
Externally published	Yes

Keywords

Antioxidant
Baker-Venkataraman rearrangement
Diaminoflavones
ROS-scavenging
Zebrafish larvae

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10.3390/molecules17078206

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title = "An alternative synthesis of 3?,4?-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae",

abstract = "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.",

keywords = "Antioxidant, Baker-Venkataraman rearrangement, Diaminoflavones, ROS-scavenging, Zebrafish larvae",

author = "Shih, {Tzenge Lien} and Hsiao, {Chih Ang} and Lin, {Zi Yu} and Chen, {Yau Hung}",

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T1 - An alternative synthesis of 3?,4?-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae

AU - Shih, Tzenge Lien

AU - Hsiao, Chih Ang

AU - Lin, Zi Yu

AU - Chen, Yau Hung

PY - 2012/7

Y1 - 2012/7

N2 - 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.

AB - 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.

KW - Antioxidant

KW - Baker-Venkataraman rearrangement

KW - Diaminoflavones

KW - ROS-scavenging

KW - Zebrafish larvae

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An alternative synthesis of 3?,4?-diaminoflavones to evaluate their antioxidant ability and cell apoptosis of zebrafish larvae

Abstract

Keywords

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