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3-Naphthylindoles as new promising candidate antioxidant, antibacterial, and antibiofilm agents

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Abstract

Indole derivatives have attracted significant attention in organic synthesis and bioactivity research owing to their substantial biological activity. In the present study, several 3-naphthylindole analogues were synthesized by direct arylation of 1-diazonaphthalene-2-(1H)-ones by rhodium(II)-catalyzed cross-coupling reaction and their antioxidant and antibacterial properties evaluated. Among the analogues tested, compound 3m displayed the highest antioxidant activity [as evaluated by ferric reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) tests], whereas compound 3c exhibited the lowest activity. The compounds were also screened against biofilm-forming bacterial species (Gram-negative Escherichia coli and Pseudomonas aeruginosa as well as Gram-positive Staphylococcus aureus and Bacillus cereus). Compounds 3b, i, j, p displayed potent antibacterial activity against E. coli. Similarly, compound 3p exhibited activity superior to quercetin (4.2 μg/mL) by completely inhibiting biofilm formation by E. coli. Moreover, the half-maximal inhibitory concentration (IC50) values of compounds 3e, j against B. cereus were comparable to that of standard quercetin.

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Acknowledgments

This study was supported by a National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (NRF-2014R1A2A1A11052391) and the Nano Material Technology Development Program (2012M3A7B4049675).

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Authors and Affiliations

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

    Kavita Sharma, Ek Raj Baral, Muhammad Saeed Akhtar & Yong Rok Lee

  2. Analysis Research Division, Daegu Center, Korea Basic Science Institute, Daegu, 702-701, Republic of Korea

    Sung Hong Kim

  3. Department of Food Science and Technology, Yeungnam University, Gyeongsan, 712-749, Republic of Korea

    Young-Jung Wee

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  1. Kavita Sharma
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  2. Ek Raj Baral
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Correspondence to Yong Rok Lee.

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Sharma, K., Baral, E.R., Akhtar, M.S. et al. 3-Naphthylindoles as new promising candidate antioxidant, antibacterial, and antibiofilm agents. Res Chem Intermed 43, 2387–2399 (2017). https://doi.org/10.1007/s11164-016-2768-4

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  • DOI: https://doi.org/10.1007/s11164-016-2768-4

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