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Molecules 2012, 17(7), 8206-8216; doi:10.3390/molecules17078206
Article

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

* ,
,
 and
*
Department of Chemistry, Tamkang University, Tamsui Dist., 25137 New Taipei City, Taiwan These authors contributed equally to this work.
* Authors to whom correspondence should be addressed.
Received: 1 June 2012 / Revised: 2 July 2012 / Accepted: 6 July 2012 / Published: 9 July 2012
(This article belongs to the Section Medicinal Chemistry)
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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 antioxidant; Baker-Venkataraman rearrangement; diaminoflavones; ROS-scavenging; zebrafish larvae
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Shih, T.-L.; Hsiao, C.-A.; Lin, Z.-Y.; Chen, Y.-H. An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae. Molecules 2012, 17, 8206-8216.

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