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\(\hbox {Re}_{2}\hbox {O}_{7}\)-catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation

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Abstract

Diverse naphtho[1,2-b]furan-3-carboxamide derivatives 12a–12q were synthesized in high yield via the novel \(\hbox {Re}_{2}\hbox {O}_{7}\)-catalyzed formal [3\(+\)2] cycloaddition of 1,4-naphthoquinones with \(\beta \)-ketoamides as the key step. This methodology offers several advantages, such as environmentally benign character, the use of a mild catalyst, high yields, and ease of handling. The synthesized compounds were screened for their tyrosinase inhibitory, antioxidant, and antibacterial activities. The results showed that compound 12c exhibited excellent tyrosinase inhibitory activity with an \(\hbox {IC}_{50}\) of \(13.48\,\upmu \hbox {g/mL}\), which is comparable to that of kojic acid (\(\hbox {IC}_{50 }= 19.45\,\upmu \hbox {g/mL}\)). Compounds 12a, 12b, and 12i displayed moderate antioxidant activities in a DPPH assay. Compound 12m showed good activity against S. aureus (\(\hbox {MIC} = 16\,\upmu \hbox {g/mL}\)), and compound 12p was found to be active against E. coli (\(\hbox {MIC} = 16\,\upmu \hbox {g/mL}\)).

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Acknowledgments

This study was supported by the Nano Material Technology Development Program through the Korean National Research Foundation (NRF) funded by the Korean Ministry of Education, Science, and Technology (2012M3A7B4049675).

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  1. School of Chemical Engineering, Yeungnam University, Gyeongsan, 712-749, Republic of Korea

    Likai Xia, Akber Idhayadhulla & Yong Rok Lee

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Xia, L., Idhayadhulla, A. & Lee, Y.R. \(\hbox {Re}_{2}\hbox {O}_{7}\)-catalyzed formal [3 + 2] cycloaddition for diverse naphtho[1,2-b]furan-3-carboxamides and their biological evaluation. Mol Divers 20, 17–28 (2016). https://doi.org/10.1007/s11030-015-9630-2

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