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Vol. 37 No. 7 (2025): Vol 37 Issue 7, 2025

Copyright (c) 2025 Paras Nath Yadav

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Synthesis, Characterization and Anticancer Potency of Copper(II) Complex of Coumarin and 4-(2-Aminoethyl)morpholine based Schiff Base

https://doi.org/10.14233/ajchem.2025.33980
Neeta Singh
Department of Chemistry, Patan Multiple Campus, Tribhuvan University, Kathmandu, Nepal; Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal
https://orcid.org/0009-0009-5008-1869
Anand Kumar Yadav
Department of Chemistry, Patan Multiple Campus, Tribhuvan University, Kathmandu, Nepal; Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal
https://orcid.org/0009-0004-0094-8130
Manoj Silwal
New Horizon English Boarding School, Rupendehi, Butwal, Nepal
https://orcid.org/0009-0009-5807-3919
Sabita Shrestha
Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal
https://orcid.org/0009-0005-3025-3783
Paras Nath Yadav
Central Department of Chemistry, Tribhuvan University, Kathmandu, Nepal
https://orcid.org/0000-0002-0661-4287

Corresponding Author(s) : Paras Nath Yadav

pnyadav219@gmail.com

Asian Journal of Chemistry, Vol. 37 No. 7 (2025): Vol 37 Issue 7, 2025

Abstract

A Schiff base ligand (L) synthesized from coumarin and 4-(2-aminoethyl)morpholine and its copper(II) complex was synthesized and characterized by elemental analysis, HRMS, UV-Vis, FT-IR, NMR and EPR spectroscopy. The IR band at 3358 cm–1 correspond to the O-H stretching vibration in the free ligand was intact and shifted to 3336 cm–1 in the complex. In 1H NMR, aromatic protons of the ligand were observed at 7.96-7.26 ppm while that of morpholine and ethylene were observed at 3.71-2.63 ppm, conforming the formation of Schiff base. Similarly, 13C NMR exhibited the peaks related to the individual carbon atoms in the ligand. Formation of the proposed ligand and complex was additionally supported by the HRMS spectra. Further, molecular structure of the ligand (L) was confirmed by X-ray crystallography having orthorhombic space group P212121. The unit cell dimensions were a = 5.4258(3) Å, b = 12.4715(9) Å, c = 23.6349(16) Å. The observed g values, g|| > g⊥ > ge (g||; 2.3559 and g⊥; 2.0669) for the complex indicated the Cu(II) ion in the square planner geometry. The anticancer potency of the compounds was performed with the MCF-7 cell line. The IC50 values of the free ligand was found 256.60 ± 0.11 µg/mL and that of complex [CuLCl2], 118.50 ± 0.40 µg/mL. Cell cycle study of [CuLCl2] complex showed a higher proportion of cells in G1 (33.18%) and S (23.40%) phases and a lower proportion of cells in G2 phase (30.91%). A molecular docking study showed binding affinity of the ligand; ΔG = -7.3 kcal/mol and it’s complex with ΔG = -8.0 kcal/mol along with H-bond interaction with protein EGFR, which indicates potential interactions with the biological targets.

Keywords

Anticancer potency Coumarin Molecular docking Morpholine Schiff base
(1)
Singh, N.; Yadav, A. K.; Silwal, M.; Shrestha, S.; Yadav, P. N. Synthesis, Characterization and Anticancer Potency of Copper(II) Complex of Coumarin and 4-(2-Aminoethyl)morpholine Based Schiff Base. ajc 2025, 37, 1785-1795.
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