Biological studies of novel aspirin-chalcone derivatives bearing variable substituents

Abdul Razak Ibrahim, . and Norsyafikah Asyilla Nordin, . and Zainab Ngaini, . Biological studies of novel aspirin-chalcone derivatives bearing variable substituents. pp. 20-31. ISSN 2180-1983

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 viaesterification of aspirin with 1a-g. All the synthesised compounds were elucidated using CHNS elemental analysis FTIR H and C 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-gand 2a-g showed no inhibition against E. coli and Staphylococcus aureusin 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.

Full text available from: Official URL: https://journal.unisza.edu.my/agrobiotechnology/in...

Abstract

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 viaesterification of aspirin with 1a-g. All the synthesised compounds were elucidated using CHNS elemental analysis FTIR H and C 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-gand 2a-g showed no inhibition against E. coli and Staphylococcus aureusin 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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Item Type:	Article
AGROVOC Term:	Chemical synthesis
AGROVOC Term:	Chalcones
AGROVOC Term:	Antibacterial agents
AGROVOC Term:	Antioxidants
AGROVOC Term:	Antiinflammatory agents
AGROVOC Term:	Chemical reagents
AGROVOC Term:	analysis
AGROVOC Term:	Free radicals
AGROVOC Term:	Hydroxylation
AGROVOC Term:	Measurement
Depositing User:	Mr. AFANDI ABDUL MALEK
Last Modified:	24 Apr 2025 00:54
URI:	http://webagris.upm.edu.my/id/eprint/9024

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