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Vol. 37 No. 6 (2025): Vol 37 Issue 6, 2025

Copyright (c) 2025 P Swarnamughi, M Kumar, P Manikandan, S Chithra, Mohd Asif, Malik Nasibullah, A. Prabakaran

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

Synthesis, Electronic, Spectroscopic and Molecular Structure Investigation on Anticancer Drug Spirooxindole-Chromene Derivative

https://doi.org/10.14233/ajchem.2025.33802
P. Swarnamughi
Department of Physics, Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0009-0119-8147
M. Kumar
Department of Physics, Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0006-6903-0488
P. Manikandan
Department of Physics, Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0003-9736-6294
S. Chithra
Department of Physics, Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0007-9576-7931
Mohd Asif
Medicinal Chemistry Laboratory-ICEIR, Department of Chemistry, Integral University, Lucknow-226026, India
https://orcid.org/0000-0002-8787-192X
Malik Nasibullah
Medicinal Chemistry Laboratory-ICEIR, Department of Chemistry, Integral University, Lucknow-226026, India
https://orcid.org/0000-0002-4413-0515
A. Prabaharan
Department of Physics, Vel Tech Rangarajan Dr Sagunthala R&D Institute of Science and Technology, Avadi, Chennai-600062, India
https://orcid.org/0000-0001-9077-8681

Corresponding Author(s) : P. Swarnamughi

saroswarna96@gmail.com

Asian Journal of Chemistry, Vol. 37 No. 6 (2025): Vol 37 Issue 6, 2025

Abstract

This work explores carbon-carbon bond formation via Michael addition in synthesizing a novel spirooxindole-chromene derivative (4) using click chemistry, examining its quantum parameters and potential anticancer effects. Spectroscopic methods, including UV-800, FT-IR and NMR, were used alongside quantum calculations (IEFPCM model) to validate the molecular structure. The compound was optimized in the gas phase with a 6-311++G(d,p) basis set and VEDA was employed for vibrational assignments. Drug-likeness properties were assessed using the ADMET online tool. In vitro studies with sixty human cancer cell lines indicated that compound 4 showed 17.88% resistance against UO-31 renal cancer cells at 10–5 M. Virtual screening identified active sites related to anticancer proteins 4DRI, 6CZ4 and 8BR9, with binding energies of -7.76, -7.3 and -6.59 kcal/mol, respectively. Ramachandran plots indicated favourable conformations for docking, with blue areas representing optimal binding positions. Ultimately, compound 4 may be enhanced for anticancer efficacy through elimination reactions at its primary amine position on the pyrano ring.

Keywords

Synthesis Indole derivative Density functional theory Anticancer activity Molecular docking
(1)
Swarnamughi, P.; Kumar, M.; Manikandan, P.; Chithra, S.; Asif, M.; Nasibullah, M.; Prabaharan, A. Synthesis, Electronic, Spectroscopic and Molecular Structure Investigation on Anticancer Drug Spirooxindole-Chromene Derivative. ajc 2025, 37, 1399-1414.
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