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<p>A series of novel quinolone-6-substituted-(1, 3, 4-thiadiazole) derivatives <b>3AA-3JJ</b> were synthesized and tested for their antimicrobial and anti-inflammatory activity. Their purity and structures were confirmed using FTIR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, and mass spectrometry techniques in addition to elemental analysis. The antimicrobial activity of the target compounds was investigated against a range of bacterial and fungal strains. Furthermore, anti-inflammatory activity was also investigated as COX-II inhibitors. The quinolone (pipemidic acid)-thiadiazole hybrid derivatives were efficient against bacterial strains. Investigations demonstrated that the synthesized compounds 3CC, 3DD, and 3II exhibited significant antibacterial activity against all tested bacterial strains, with minimum inhibitory concentrations (MICs) of 10&#xa0;µg/mL, outperforming the parent drug, pipemidic acid (MIC 16&#xa0;µg/mL), and showing comparable efficacy to the reference drug, ciprofloxacin (MIC 0.5&#xa0;µg/mL). However, the compound 3AA-3II did not exhibit activity against the fungal strain <i>Candida albicans</i>. Furthermore, compound 3JJ showed considerable <i>cyclooxygenase-II</i> (COX-II) inhibition, achieving a 39.9% inhibition rate. Molecular docking studies revealed that compounds 3CC, 3DD, and 3II demonstrated strong hydrogen bonding interactions with key amino acid residues (ARG57, MET16, HIS45, GLY96, ARG98, ARG74, and ARG137) and exhibited binding energies ranging from − 7.64 to -8.05&#xa0;kcal/mol within the active site of the DNA gyrase enzyme. These findings highlight the strong binding affinity of quinolone-substituted 1,3,4-thiadiazole hybrids.</p> Graphical Abstract <p></p>

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Design, Synthesis, and Evaluation of Novel Quinolone-6-Substituted-(1, 3, 4-Thiadiazole) Derivatives as Antimicrobial and Anti-Inflammatory Agents

  • 期刊论文

  • 发表日期：

    2025年8月13日

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  • Vishal Sharma,
  • Rina Das,
  • Diksha Sharma,
  • Dinesh Kumar Mehta

摘要

A series of novel quinolone-6-substituted-(1, 3, 4-thiadiazole) derivatives 3AA-3JJ were synthesized and tested for their antimicrobial and anti-inflammatory activity. Their purity and structures were confirmed using FTIR, 1H NMR, 13C NMR, and mass spectrometry techniques in addition to elemental analysis. The antimicrobial activity of the target compounds was investigated against a range of bacterial and fungal strains. Furthermore, anti-inflammatory activity was also investigated as COX-II inhibitors. The quinolone (pipemidic acid)-thiadiazole hybrid derivatives were efficient against bacterial strains. Investigations demonstrated that the synthesized compounds 3CC, 3DD, and 3II exhibited significant antibacterial activity against all tested bacterial strains, with minimum inhibitory concentrations (MICs) of 10 µg/mL, outperforming the parent drug, pipemidic acid (MIC 16 µg/mL), and showing comparable efficacy to the reference drug, ciprofloxacin (MIC 0.5 µg/mL). However, the compound 3AA-3II did not exhibit activity against the fungal strain Candida albicans. Furthermore, compound 3JJ showed considerable cyclooxygenase-II (COX-II) inhibition, achieving a 39.9% inhibition rate. Molecular docking studies revealed that compounds 3CC, 3DD, and 3II demonstrated strong hydrogen bonding interactions with key amino acid residues (ARG57, MET16, HIS45, GLY96, ARG98, ARG74, and ARG137) and exhibited binding energies ranging from − 7.64 to -8.05 kcal/mol within the active site of the DNA gyrase enzyme. These findings highlight the strong binding affinity of quinolone-substituted 1,3,4-thiadiazole hybrids.

Graphical Abstract