A New Sustainable Approach to Antibiotic Resistance: Development of bis‐Quaternary Ammonium Salts From 2,4,6‐Trichloro‐1,3,5‐Triazine

The development of highly effective antibiotics and antimicrobials over the centuries has greatly improved human life. However, the irresponsible use of these substances and their release into the environment have led to the emergence of resistant microorganisms. Quaternary ammonium salts (QAS), due to their high efficacy as antibacterial agents and their wide spectrum of activity as disinfectants and antiseptics, represent a possibility to avoid antibiotic resistance. In this work, new bis‐cationic QAS, having as common precursor 2,4,6‐trichloro‐1,3,5‐triazine, were synthetized showing high antimicrobial properties (bis‐TQAS). The compounds obtained were characterized by 1 H NMR, 13 C NMR, COSY, HSQC, HMQC, ESI‐MS, elemental analysis, and Log P determination. Their antibacterial activity was evaluated against Klebsiella pneumoniae , Escherichia coli , Staphylococcus aureus , and Listeria monocytogenes . Significant growth inhibition was achieved for all tested strains. Specifically, for the bis‐TQAS with C 10 alkyl chain, a Log reduction of >5.70 against S. aureus and L. monocytogenes was observed, while the antibacterial Log reduction exceeded 3.60 Log for K. pneumoniae and E. coli strains. In contrast, the performance of the C 12 alkyl chain derivative varied; nevertheless, it still demonstrated strong efficacy, with Log reductions exceeding 3.63 for the Gram‐positive strains and 4.00 for the Gram‐negative strains.

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Publication Details

Journal
ChemMedChem
Published
2026-08-27
DOI
https://doi.org/10.1002/cmdc.70458
Primary Topic
Synthesis and Characterization of Heterocyclic Compounds
Type
article
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article

A New Sustainable Approach to Antibiotic Resistance: Development of bis‐Quaternary Ammonium Salts From 2,4,6‐Trichloro‐1,3,5‐Triazine

Manuela Facchin, Arianna De Luca, Andrea Gattolin, Patrizio Raffa et al.
ChemMedChem
Synthesis and Characterization of Heterocyclic Compounds
article

A New Sustainable Approach to Antibiotic Resistance: Development of bis‐Quaternary Ammonium Salts From 2,4,6‐Trichloro‐1,3,5‐Triazine

Manuela Facchin, Arianna De Luca, Andrea Gattolin, Patrizio Raffa, Valentina Beghetto, Rachele Rampazzo
article en

Abstract

The development of highly effective antibiotics and antimicrobials over the centuries has greatly improved human life. However, the irresponsible use of these substances and their release into the environment have led to the emergence of resistant microorganisms. Quaternary ammonium salts (QAS), due to their high efficacy as antibacterial agents and their wide spectrum of activity as disinfectants and antiseptics, represent a possibility to avoid antibiotic resistance. In this work, new bis‐cationic QAS, having as common precursor 2,4,6‐trichloro‐1,3,5‐triazine, were synthetized showing high antimicrobial properties (bis‐TQAS). The compounds obtained were characterized by 1 H NMR, 13 C NMR, COSY, HSQC, HMQC, ESI‐MS, elemental analysis, and Log P determination. Their antibacterial activity was evaluated against Klebsiella pneumoniae , Escherichia coli , Staphylococcus aureus , and Listeria monocytogenes . Significant growth inhibition was achieved for all tested strains. Specifically, for the bis‐TQAS with C 10 alkyl chain, a Log reduction of >5.70 against S. aureus and L. monocytogenes was observed, while the antibacterial Log reduction exceeded 3.60 Log for K. pneumoniae and E. coli strains. In contrast, the performance of the C 12 alkyl chain derivative varied; nevertheless, it still demonstrated strong efficacy, with Log reductions exceeding 3.63 for the Gram‐positive strains and 4.00 for the Gram‐negative strains.

ChemMedChemVol. 21(17)
Ca' Foscari University of Venice (IT), University of Groningen (NL), AULSS 2 Marca Trevigiana (IT), Dialyse Centrum Groningen (NL), Industriale Chimica (Italy) (IT), Consorzio Interuniversitario Reattività Chimica e Catalisi (IT), University of Campania "Luigi Vanvitelli" (IT)
Responsible consumption and production
Openalex Percentile: Top 19%
Synthesis and Characterization of Heterocyclic Compounds
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