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Research Article

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Donatella VerbanacUniversity of Zagreb School of Medicine, Center for Translational and Clinical Research, Zagreb, Croatia,

Ritu MalikDepartment of Chemistry, University of Delhi, Delhi, India,

Mahesh ChandDepartment of Chemistry, University of Delhi, Delhi, India,

Khushbu KushwahaDepartment of Chemistry, University of Delhi, Delhi, India,

Monika VashistDepartment of Chemistry, University of Delhi, Delhi, India,

Mario MatijašićUniversity of Zagreb School of Medicine, Center for Translational and Clinical Research, Zagreb, Croatia,

Višnja StepanićLaboratory for Epigenomics, Division of Molecular Medicine, Ruđer Bošković Institute, Zagreb, Croatia, and

Mihaela PerićUniversity of Zagreb School of Medicine, Center for Translational and Clinical Research, Zagreb, Croatia,

Hana Čipčić PaljetakUniversity of Zagreb School of Medicine, Center for Translational and Clinical Research, Zagreb, Croatia,

Luciano SasoDepartment of Physiology and Pharmacology ‘Vittorio Ersparmer’, Sapienza University of Rome, Rome, Italy

Subhash C. JainDepartment of Chemistry, University of Delhi, Delhi, India, Correspondence[email protected]

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Figures & data

Scheme 1. Synthesis of quinolone–triazole conjugates (12nju). Reagents and conditions: ai = NaOH, H₂O, ref lux, 4–6 h; b–= abs. C₂H₅OH, conc. H₂SO₄, ref lux, 18–20 h; c8 = N₂H₄ H₂O, heat, 50–60 °C, 4–6 h; d–= aldehyde, glc. CH₃COOH, CH₃COONH₄, 6–8 h at room temperature.

Scheme 1. Synthesis of quinolone–triazole conjugates (12nju). Reagents and conditions: ai = NaOH, H2O, ref lux, 4–6 h; b–= abs. C2H5OH, conc. H2SO4, ref lux, 18–20 h; c8 = N2H4 H2O, heat, 50–60 °C, 4–6 h; d–= aldehyde, glc. CH3COOH, CH3COONH4, 6–8 h at room temperature.

Table 1. The results of compound cytotoxicity screening expressed as IC₅₀ values in μM.

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Table 2. Comparison of calculated gas-phase (g) bond dissociation enthalpies (BDE) and corresponding aqueous (aq) free energies (all given in kJ/mol) as well as estimated lipophilicity values logP of the 5‐aryl-4H‐1,2,4‐triazolyl derivatives and natural polyphenols. Experimentally determined radical scavenging (DPPH assay) and cellular antioxidant (CAA) activities are also presented.

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Supplemental material

IENZ_1190714_Supplementary_Material.pdf

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Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Table 1. The results of compound cytotoxicity screening expressed as IC₅₀ values in μM.

IENZ_1190714_Supplementary_Material.pdf

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Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

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Table 1. The results of compound cytotoxicity screening expressed as IC50 values in μM.

IENZ_1190714_Supplementary_Material.pdf

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Table 1. The results of compound cytotoxicity screening expressed as IC₅₀ values in μM.