Biological studies of novel aspirin-chalcone derivatives bearing variable substituents
The evolution of drug resistant bacteria has now becoming a major concern in the search for new antibacterial agent. Ongoing interest has also developing to find a new class of compounds with antioxidant properties. Herein, a series of hydroxylated chalcones 1a-g and aspirin-chalcone derivatives 2...
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| Main Authors: | , , |
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| Format: | Article |
| Language: | English English |
| Published: |
2020
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| Subjects: | |
| Online Access: | http://eprints.unisza.edu.my/7243/1/FH02-FF-20-42809.pdf http://eprints.unisza.edu.my/7243/2/FH02-FF-20-47839.pdf http://eprints.unisza.edu.my/7243/ |
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| Summary: | The evolution of drug resistant bacteria has now becoming a major concern in the search for new
antibacterial agent. Ongoing interest has also developing to find a new class of compounds with antioxidant
properties. Herein, a series of hydroxylated chalcones 1a-g and aspirin-chalcone derivatives 2a-g were
successfully synthesised for antibacterial and antioxidant properties. Chalcones 1a-g were prepared by
Claisen-Schmidt condensation of 4-hydroxyacetophenone and benzaldehyde derivatives, while 2a-g were
synthesised via esterification of aspirin with 1a-g. All the synthesised compounds were elucidated using
CHNS elemental analysis, FTIR, 1H and 13C NMR spectroscopy, and X-ray crystallography. All compounds
were evaluated for antibacterial assay via disc diffusion method and antioxidant assay using stable free radical
2,2-diphenyl-1-picrylhydrazyl (DPPH). Only 1a showed moderate activity against Escherichia coli, while 1b-g
and 2a-g showed no inhibition against E. coli and Staphylococcus aureus in comparison ampicillin as standard
antibiotic. Compounds 1b-g and 2a-g having various substituents contributed to bulky molecular structures
and caused difficult penetration into the cell membrane thus, unable to inhibit the bacterial growth.
Compounds 1a-g and 2a-g also displayed poor antioxidant properties on DPPH in comparison to ascorbic
acid due to low phenolic pharmacophore. The formation of bulky structures for 2a-g have hindered the
antioxidant properties compared to 1a-g. |
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