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<p>In pursuit of novel antimicrobial agents, a series of thiazolo[5,4-f]quinoline derivatives incorporating pyridine and thiophene moieties were synthesized and structurally characterized using IR and <sup>1</sup>H-NMR spectroscopy. The synthetic strategy employed diverse condensation and cyclization reactions involving cyanoacetamide intermediates, aryl isothiocyanates, and α-halocarbonyl compounds. The resulting compounds were evaluated for their antimicrobial efficacy against <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i>. Notably, compounds <b>18</b>, <b>19</b>, and <b>23</b> exhibited potent broad-spectrum activity, surpassing standard drugs such as chloramphenicol and cephalothin in several assays (MIC = 3.125–6.25&#xa0;µg/mL). Structure-activity relationship (SAR) analysis revealed that the incorporation of bulky, lipophilic aromatic systems and electron-withdrawing substituents significantly enhanced antimicrobial potency. Molecular docking studies further supported these findings, with compound <b>19</b> demonstrating the strongest binding affinity (-6.6951&#xa0;kcal/mol) to bacterial DNA gyrase (PDB: 6F86) via a synergistic network of hydrogen bonds and π-interactions. These results highlight the thiazoloquinoline framework, particularly derivatives bearing thiophene and naphthoyl functionalities, as a promising scaffold for future antimicrobial drug development.</p>

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Exploring novel thiazolo[5,4-f]quinoline-based scaffolds as promising antimicrobial agents through synthesis and molecular insights

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年8月26日

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  • Nanees N. Soliman,
  • Ahmed A. Fadda,
  • Hatem E. Gaffer,
  • Nesma M. Bayoumy

摘要

In pursuit of novel antimicrobial agents, a series of thiazolo[5,4-f]quinoline derivatives incorporating pyridine and thiophene moieties were synthesized and structurally characterized using IR and 1H-NMR spectroscopy. The synthetic strategy employed diverse condensation and cyclization reactions involving cyanoacetamide intermediates, aryl isothiocyanates, and α-halocarbonyl compounds. The resulting compounds were evaluated for their antimicrobial efficacy against Staphylococcus aureus, Escherichia coli, and Candida albicans. Notably, compounds 18, 19, and 23 exhibited potent broad-spectrum activity, surpassing standard drugs such as chloramphenicol and cephalothin in several assays (MIC = 3.125–6.25 µg/mL). Structure-activity relationship (SAR) analysis revealed that the incorporation of bulky, lipophilic aromatic systems and electron-withdrawing substituents significantly enhanced antimicrobial potency. Molecular docking studies further supported these findings, with compound 19 demonstrating the strongest binding affinity (-6.6951 kcal/mol) to bacterial DNA gyrase (PDB: 6F86) via a synergistic network of hydrogen bonds and π-interactions. These results highlight the thiazoloquinoline framework, particularly derivatives bearing thiophene and naphthoyl functionalities, as a promising scaffold for future antimicrobial drug development.