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

doi:10.3390/molecules17078206

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

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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^† and Yau-Hung Chen*

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; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(7):8206-8216.

Chicago/Turabian Style

Shih, Tzenge-Lien; Hsiao, Chih-Ang; Lin, Zi-Yu; Chen, Yau-Hung. 2012. "An Alternative Synthesis of 3′,4′-Diaminoflavones to Evaluate Their Antioxidant Ability and Cell Apoptosis of Zebrafish Larvae." Molecules 17, no. 7: 8206-8216.

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