Synthesis and antibiofilm activity of 1,2,3-triazole-pyridine hybrids against methicillin-resistant Staphylococcus aureus (MRSA)

• Published in: New journal of chemistry Vol. 45; no. 24; pp. 10822 - 10830
• Main Authors: El Malah, Tamer, Soliman, Hanan A., Hemdan, Bahaa A., Abdel Mageid, Randa E., Nour, Hany F.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 28.06.2021; Royal Society of Chemistry
• Subjects: Alkylation; Alkynes; Antibiotics; Aromatic compounds; Chemical compounds; Chemistry; Chemistry, Multidisciplinary; Cycloaddition; Fourier transforms; Infrared spectroscopy; NMR; Nuclear magnetic resonance; Physical Sciences; Pyridines; Science & Technology; Staphylococcus infections; Triazoles; Vancomycin; DESIGN; BIOLOGICAL EVALUATION; ANTIBACTERIAL; AGENTS; BIOFILM; AZIDE; IDENTIFICATION; MOLECULAR DOCKING; DERIVATIVES; CYTOTOXICITY
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/D1NJ00773D

Antibiotic-resistant bacteria are emerging at an alarming rate, posing a potential threat to human health. We synthesised alkyne-functionalised pyridines 3 and 4 via alkylation of substituted 2-oxo-1,2-dihydropyridine derivatives 1 and 2 with propargyl bromide in alkaline DMF. The reactions afforded the O -propagylated compounds 3 and 4 as the main products. Copper( i )-catalysed azide–alkyne cycloaddition of compounds 3 and 4 with aromatic azides furnishes compounds 11–22 . The chemical structures of the 1,2,3-triazole-pyridine hybrids 11–22 were fully verified using different spectroscopic tools, such as FT-IR, 1 H NMR, 13 C NMR, and 2D NMR. We evaluated in vitro antibacterial and antibiofilm activities of the 1,2,3-triazole-pyridine hybrids 11–22 against methicillin-resistant Staphylococcus aureus (MRSA) in both planktonic and sessile cells. Compounds 17 , 18 , and 21 exhibited promising growth inhibition activity against planktonic and sessile MRSA cells with IC 50 = 34.94, 37.91, and 43.88 μM, respectively. The antibiofilm activities of the new compounds were evaluated using Vancomycin (Van) as a standard reference drug (IC 50 186.0 μM).