Synthesis and antibiofilm activity of 1,2,3-triazole-pyridine hybrids against methicillin-resistant Staphylococcus aureus (MRSA)
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...
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| Published in | New journal of chemistry Vol. 45; no. 24; pp. 10822 - 10830 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
CAMBRIDGE
Royal Soc Chemistry
28.06.2021
Royal Society of Chemistry |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1144-0546 1369-9261 |
| DOI | 10.1039/D1NJ00773D |
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| Abstract | 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). |
|---|---|
| AbstractList | 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). 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). 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, H-1 NMR, C-13 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 mu M, respectively. The antibiofilm activities of the new compounds were evaluated using Vancomycin (Van) as a standard reference drug (IC50 186.0 mu M). |
| Author | El Malah, Tamer Nour, Hany F. Soliman, Hanan A. Hemdan, Bahaa A. Abdel Mageid, Randa E. |
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| Keywords | DESIGN BIOLOGICAL EVALUATION ANTIBACTERIAL AGENTS BIOFILM AZIDE IDENTIFICATION MOLECULAR DOCKING DERIVATIVES CYTOTOXICITY |
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| Snippet | Antibiotic-resistant bacteria are emerging at an alarming rate, posing a potential threat to human health. We synthesised alkyne-functionalised pyridines
3
and... Antibiotic-resistant bacteria are emerging at an alarming rate, posing a potential threat to human health. We synthesised alkyne-functionalised pyridines 3 and... |
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| SubjectTerms | 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 |
| Title | Synthesis and antibiofilm activity of 1,2,3-triazole-pyridine hybrids against methicillin-resistant Staphylococcus aureus (MRSA) |
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