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<p>The rise of multidrug-resistant (MDR) pathogens highlights the need for novel antimicrobial agents. This study reports the synthesis of two 1-aminoalkyl-2-naphthol derivatives, 1-(dimethylaminomethyl)naphthalen-2-ol (<b>2</b>) and 1-(piperidin-1-ylmethyl)naphthalen-2-ol (<b>3</b>), <i>via</i> the Betti base reaction using 2-naphthol, formaldehyde, and secondary amines. Structural confirmation was achieved through the <sup>1</sup>H and <sup>13</sup>C-NMR. Antimicrobial screening against 26 bacterial and 4 fungal strains revealed that compound <b>3</b> exhibited potent antibacterial activity against MDR strains, with a minimum inhibitory concentration (MIC) value as low as 10 µg/mL against <i>Pseudomonas aeruginosa</i> MDR1. Compound <b>3</b> also demonstrated superior efficacy against <i>Staphylococcus aureus</i> MDR strains, with an MIC of 100 µg/mL, compared to ciprofloxacin, which had an MIC of 200 µg/mL. Its lower MIC values compared to ciprofloxacin suggests that compound <b>3</b> has potential for treating infections caused by multidrug-resistant <i>S. aureus</i>. Compound <b>2</b> showed strong antifungal activity against <i>Penicillium notatum</i> and <i>P. funiculosum</i>, with an MIC of 400 µg/mL, outperforming griseofulvin (MIC = 500 µg/mL). Molecular docking further supported these findings, with compound <b>3</b> displaying strong binding affinities to <i>E. coli</i> DNA gyrase (‒6.755 kcal/mol; PDB ID: 5MMN) and <i>Candida albicans</i> lanosterol 14α-demethylase (‒7.813 kcal/mol; PDB ID: 5V5Z). Overall, these results underscore the potential of 1-aminoalkyl-2-naphthol derivatives as promising candidates for combating drug-resistant infections.</p>

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Synthesis, in vitro antimicrobial activity, and in silico studies of 1-aminoalkyl-2-naphthols

  • 期刊论文

  • 出版模式：

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  • 发表日期：

    2025年11月10日

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  • Frehiwot Beyene,
  • Avijit Mazumder,
  • Solomon Tadesse,
  • Kaleab Asres,
  • Daniel Bisrat

摘要

The rise of multidrug-resistant (MDR) pathogens highlights the need for novel antimicrobial agents. This study reports the synthesis of two 1-aminoalkyl-2-naphthol derivatives, 1-(dimethylaminomethyl)naphthalen-2-ol (2) and 1-(piperidin-1-ylmethyl)naphthalen-2-ol (3), via the Betti base reaction using 2-naphthol, formaldehyde, and secondary amines. Structural confirmation was achieved through the 1H and 13C-NMR. Antimicrobial screening against 26 bacterial and 4 fungal strains revealed that compound 3 exhibited potent antibacterial activity against MDR strains, with a minimum inhibitory concentration (MIC) value as low as 10 µg/mL against Pseudomonas aeruginosa MDR1. Compound 3 also demonstrated superior efficacy against Staphylococcus aureus MDR strains, with an MIC of 100 µg/mL, compared to ciprofloxacin, which had an MIC of 200 µg/mL. Its lower MIC values compared to ciprofloxacin suggests that compound 3 has potential for treating infections caused by multidrug-resistant S. aureus. Compound 2 showed strong antifungal activity against Penicillium notatum and P. funiculosum, with an MIC of 400 µg/mL, outperforming griseofulvin (MIC = 500 µg/mL). Molecular docking further supported these findings, with compound 3 displaying strong binding affinities to E. coli DNA gyrase (‒6.755 kcal/mol; PDB ID: 5MMN) and Candida albicans lanosterol 14α-demethylase (‒7.813 kcal/mol; PDB ID: 5V5Z). Overall, these results underscore the potential of 1-aminoalkyl-2-naphthol derivatives as promising candidates for combating drug-resistant infections.