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Synthesis, antioxidant, and antibacterial studies of phenolic esters and amides of 2-(1-benzofuran-2-yl) quinoline-4-carboxylic acid

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Abstract

A new series of phenolic esters 2(a–j) and amides 3(a–c) of 2-(1-benzofuran-2-yl) quinoline-4-carboxylic acid were synthesized by the reaction of 2-(1-benzofuran-2-yl)-quinoline-4-carboxylic acid (1) with various substituted phenols and secondary amines using ethyl-(N′,N′-dimethylamino)propyl carbodiimide hydrochloride (EDC.HCl) as a coupling agent. The newly synthesized compounds were evaluated for in vitro antioxidant and antibacterial activity. Among all tested compounds 2a, 2c, 2e, and 2h showed good chelating ability with Fe+2 ions, whereas compounds 2g and 2j exhibited good scavenging activity with DPPH free radicals. Concerning antibacterial activities compounds 2a, 2b, 2c, and 2h were found to be equipotent to ampicillin against Enterococcus sp and Staphylococcus aureus, while compound 2e is found to be as potent as ampicillin against Pantoea Dispersa and Ochrobactrum sp. amide derivatives 3(a–c) were found to be less potent when compared to standard.

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Acknowledgments

The authors are thankful to IISc Bangalore for providing spectral data. One of the authors (Sheelavanth S) is thankful to DST-Govt. of India, for awarding Inspire fellowship.

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Authors and Affiliations

  1. Department of P.G. Studies and Research in Industrial Chemistry, School of Chemical Sciences, Kuvempu University, Jnana Sahyadri, Shankarghatta 577 451, Shivamogga Dist, Karnataka, India

    Sheelavanth Shankerrao & Yadav D. Bodke

  2. Department of Botany, Gulbarga University, Jnana Ganga, Gulbarga, 585 106, Karnataka, India

    Sundar S. Mety

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  1. Sheelavanth Shankerrao
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  2. Yadav D. Bodke
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  3. Sundar S. Mety
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Correspondence to Yadav D. Bodke.

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Shankerrao, S., Bodke, Y.D. & Mety, S.S. Synthesis, antioxidant, and antibacterial studies of phenolic esters and amides of 2-(1-benzofuran-2-yl) quinoline-4-carboxylic acid. Med Chem Res 22, 1163–1171 (2013). https://doi.org/10.1007/s00044-012-0117-8

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  • DOI: https://doi.org/10.1007/s00044-012-0117-8

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