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Synthesis, antimicrobial, and antioxidant activity of benzofuran barbitone and benzofuran thiobarbitone derivatives

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Abstract

The synthesis of novel series of benzofuran derivatives, containing barbitone moiety, 5-[(2/4-substitutedphenyl)(5-substituted-1-benzofuran-2-yl) methylidene]pyrimidin-2,4,6(1H,3H,5H)-trione (4a–i) and thiobarbitone moiety, 5-[(2/4-substitutedphenyl)(5-substituted-1-benzofuran-2-yl)methylidene]-2-thioxodihydropyrimidin-4,6(1H, 5H)-dione (5a–i) have been reported. The target compounds (4a–i) and (5a–i) were synthesized by the Knoevenagel condensation of (5-substituted-1-benzofuran-2-yl)(2/4-substitutedphenyl) methanone (3a–i) with barbituric acid and thiobarbituric acid, respectively, in acid medium. These compounds were screened for the antimicrobial and antioxidant activities. From antimicrobial activity results it was found that compounds 4a, 5a, 4c, and 5c displayed good antibacterial and antifungal activity against all tested strains. Further, the synthesized compounds were studied for docking on the enzyme, Glucosamine-6-phosphate synthase and the compounds 4c and 5c have emerged has an active antimicrobial agent with least binding energy (−5.27 and −4.85 kJ mol−1). Compounds 4e, 4f, 5e, and 5f showed promising free radical scavenging activity and compounds 5a and 5b showed good chelating ability with Fe2+ ions.

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Acknowledgments

The authors are thankful to the Chairman, Department of Industrial Chemistry, Kuvempu University, Shankaraghatta for providing the laboratory facilities. One of the authors (Kenchappa. R) is thankful to the UGC for the award of Rajiv Gandhi National Fellowship (RGNF).

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Authors and Affiliations

  1. Department of P.G. Studies and Research in Industrial Chemistry, Jnana Sahyadri, Kuvempu University, Shankaraghatta, Shivamogga, 577451, Karnataka, India

    R. Kenchappa, Yadav D. Bodke & M. Aruna Sindhe

  2. Department of P.G. Studies and Research in Applied Botany, Jnana Sahyadri, Kuvempu University, Shankaraghatta, Shivamogga, 577451, Karnataka, India

    B. Asha

  3. Department of P.G. Studies and Research in Biotechnology, Jnana Sahyadri, Kuvempu University, Shankaraghatta, Shivamogga, 577451, Karnataka, India

    Sandeep Telkar

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  1. R. Kenchappa
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  2. Yadav D. Bodke
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  3. B. Asha
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  4. Sandeep Telkar
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  5. M. Aruna Sindhe
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Correspondence to Yadav D. Bodke.

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Kenchappa, R., Bodke, Y.D., Asha, B. et al. Synthesis, antimicrobial, and antioxidant activity of benzofuran barbitone and benzofuran thiobarbitone derivatives. Med Chem Res 23, 3065–3081 (2014). https://doi.org/10.1007/s00044-013-0892-x

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