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Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Copyright (c) 2024 VISAL C. LORENSU HEWAGE, MEDHA J. GUNARATNA, NISHAL M. EGODAWATHTHA, NASRI NESNAS

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This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Anti-inflammatory Activities of 4-Arylidene-2-phenyloxazol-5(4H)-one Derivatives

https://doi.org/10.14233/ajchem.2024.31957
Visal C. Lorensu Hewage
Faculty of Graduate Studies, University of Kelaniya, Kelaniya, Sri Lanka
https://orcid.org/0009-0006-8847-3313
Medha J. Gunaratna
Department of Chemistry, Faculty of Science, University of Kelaniya, Kelaniya, Sri Lanka
https://orcid.org/0000-0002-4465-5469
Nishal M. Egodawaththa
Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA
https://orcid.org/0000-0002-4191-4322
Nasri Nesnas
Department of Chemistry and Chemical Engineering, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA
https://orcid.org/0000-0003-3511-940X

Corresponding Author(s) : Medha J. Gunaratna

medhagunaratna@kln.ac.lk

Asian Journal of Chemistry, Vol. 36 No. 8 (2024): Vol 36 Issue 8, 2024

Abstract

In this study, four different 4-arylidene-2-phenyloxazol-5(4H)-ones (5a-d), were synthesized via the Erlenmeyer-Plöchl reaction and characterized by FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques. Evaluation of their in vitro anti-inflammatory activities using the heat-induced human red blood cell (HRBC) membrane stabilization assay revealed concentration dependent inhibitory effects. The IC50 values of 5a, 5b, 5c and 5d were reported as 4.65 ± 0.22 mM, 7.34 ± 0.28 mM, 5.23 ± 0.18 mM and 1.96 ± 0.09 mM, respectively. O-Acetyl salicylic acid as standard showed its IC50 value at 6.41 ± 0.18 mM. Docking studies against human cyclooxygenase (COX) 1 and 2 revealed affinities of the compounds to binding cavities of COX enzymes. Particularly, compound 5d exhibited remarkable activity in both HRBC membrane stabilization and the formation of hydrogen bonds with binding cavities. This suggests a potential correlation between the number of hydroxyl groups of oxazolone derivatives and the enhancement of anti-inflammatory activity.

Keywords

Oxazolones Anti-inflammatory Erlenmeyer-Plöchl reaction HRBC membrane stabilization
Hewage, V. C. L., Gunaratna, M. J., Egodawaththa, N. M., & Nesnas, N. (2024). Synthesis and Anti-inflammatory Activities of 4-Arylidene-2-phenyloxazol-5(4H)-one Derivatives. Asian Journal of Chemistry, 36(8), 1872–1880. https://doi.org/10.14233/ajchem.2024.31957
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