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

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

  • Sci Rep. 2025 Nov 10;15(1):39278. doi: 10.1038/s41598-025-23064-1.
Frehiwot Beyene 1,  Avijit Mazumder 2,  Solomon Tadesse 3,  Kaleab Asres 1,  Daniel Bisrat 4
Affiliations

Affiliations

  • 1 Department of Pharmaceutical Chemistry and Pharmacognosy, School of Pharmacy, College of Health Sciences, Addis Ababa University, P. O. Box 1176, Addis Ababa, Ethiopia.
  • 2 Department of Pharmacology, Noida Institute of Engineering and Technology (Pharmacy Institute), Institutional Area, 19 Knowledge Park II, Greater Noida, 201306, India.
  • 3 Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, Idaho State University, 921 South 8th Avenue, Stop 8333, Pocatello, ID, 83209-8333, USA.
  • 4 Department of Pharmaceutical Chemistry and Pharmacognosy, School of Pharmacy, College of Health Sciences, Addis Ababa University, P. O. Box 1176, Addis Ababa, Ethiopia. [email protected].
PMID: 41214095 DOI: 10.1038/s41598-025-23064-1
Abstract

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.

Keywords

1-Aminoalkyl-2-naphthol; 2-Naphthol; ADMET; Antimicrobial; Betti base; Molecular docking.

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