Synthesis and antibiofilm activity of 1,2,3-triazole-pyridine hybrids against methicillin-resistant Staphylococcus aureus (MRSA)†
*a
Hanan A.
Soliman,
a
Bahaa A.
Hemdan,
b
Randa E.
Abdel Mageid
a
and
Hany F.
Nour
*a
Abstract
Antibiotic-resistant bacteria are emerging at an alarming rate, posing a potential threat to human health. We synthesised alkyne-functionalised pyridines 3 and 4via 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, 1H NMR, 13C 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 IC50 = 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 (IC50 186.0 μM).
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