Biological Studies of Novel Aspirin-Chalcone Derivatives bearing Variable Substituents

  • Norsyafikah Asyilla Nordin Faculty of Pharmacy, Universiti Sultan Zainal Abidin, Besut Campus, 22200 Besut, Terengganu, Malaysia.
  • Abdul Razak Ibrahim School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.
  • Zainab Ngaini Department of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia.
Keywords: Synthesis, chalcone, aspirin, antibacterial activity, antioxidant activity

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 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.

Published
08-03-2020
How to Cite
Nordin, N. A., Ibrahim, A. R., & Ngaini, Z. (2020). Biological Studies of Novel Aspirin-Chalcone Derivatives bearing Variable Substituents. Journal Of Agrobiotechnology, 11(1), 20-31. https://doi.org/10.37231/jab.2020.11.1.185
Section
Articles