Synthesis, in silico and inhibition evaluations of carvone derivatives as potential neuraminidase inhibitors

Jusoh, Noorakmar and Abd Hamid, Shafida and Abdul Hamid, Azzmer Azzar and Abd Halim, Khairul Bariyyah and Muhamad Bunnori, Noraslinda (2025) Synthesis, in silico and inhibition evaluations of carvone derivatives as potential neuraminidase inhibitors. Pharmaceutical Chemistry Journal, 59 (7). pp. 753-767. ISSN 0091-150X E-ISSN 1573-9031

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Abstract

The pathogenic influenza virus infects the human respiratory tract, causing seasonal outbreaks and pandemics across the globe. Vaccination and anti-influenza drugs are the current strategies used to combat this disease, although new drugs are urgently needed owing to the increasing emergence of antiviral resistance of the existing drugs. Herein, we report the synthesis of a series of carvone derivatives. The compounds were characterized by the FT-IR, ESI-MS, 1 H NMR, and 13C NMR spectroscopy, and their binding affinities were evaluated in silico. Molecular docking of the derivatives in the neuraminidase (NA) active site (PDB ID: 3TI6) showed compound 3e to display the best binding energy at –8.35 kcal/mol, comparable with oseltamivir (OTV) (–8.58 kcal/mol), followed by 3b (–8.03 kcal/mol) and 7 (–7.46 kcal/mol). The molecular dynamics simulations of the protein–ligand complexes showed that both 3e-NA and OTV–NA complexes were comparable in stability and flexibility. Compound 3e also showed the highest inhibition percentage at 1000 mg/mL (60.95%) followed by 3b (59.21%), 7 (54.17%), and 4 (51.14%). Compound 3b gave the highest inhibitory activity of the series with IC50 = 29.53 mM, followed by 4 (35.50 �M), 3e (44.13 �M), and 7 (52.83 �M). The studies indicate the potential of these derivatives to be designed and developed as effective neuraminidase inhibitors.

Item Type:	Article (Journal)
Uncontrolled Keywords:	influenza; neuraminidase; molecular docking; carvone; molecular dynamics.
Subjects:	Q Science > QD Chemistry R Medicine > RM Therapeutics. Pharmacology
Kulliyyahs/Centres/Divisions/Institutes (Can select more than one option. Press CONTROL button):	Kulliyyah of Science > Department of Chemistry Kulliyyah of Science
Depositing User:	Dr Shafida Abd Hamid
Date Deposited:	27 Nov 2025 16:13
Last Modified:	27 Nov 2025 16:13
Queue Number:	2025-11-Q239
URI:	http://irep.iium.edu.my/id/eprint/124725

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