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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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