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Vol. 37 No. 10 (2025): Vol 37 Issue 10, 2025

Copyright (c) 2025 S Rekha, S Tamilselvan, Mohd Asif, Malik Nasibullah, J. N. Cheerlin Mishma, P Manikandan, S Kaleeswaran

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

Synthesis, Spectroscopic, Electronic Charge Transfer and Non-covalent Interactions Studies on (E)-5-Bromo-3-((3-chloro-4-fluorophenyl)imino)indolin-2-one: In vitro Studies against the Cancer Cell Lines

https://doi.org/10.14233/ajchem.2025.34165
S. Rekha
Department of Physics Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0007-0181-7783
S. Tamilselvan
Department of Physics Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0000-0002-8285-4039
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
J.N. Cheerlin Mishma
Department of Physics, Rohini College of Engineering and Technology, Palkulam, Kanyakumari-629702, India
https://orcid.org/0009-0001-8287-4654
P. Manikandan
Department of Physics Arignar Anna Government Arts College, Cheyyar-604407, India
https://orcid.org/0009-0003-9736-6294
S. Kaleeswaran
Department of Physics, Madras Christian College, East Tambaram, Chennai-600059, India
https://orcid.org/0009-0005-8301-0048

Corresponding Author(s) : S. Tamilselvan

tamilraji1977@gmail.com

Asian Journal of Chemistry, Vol. 37 No. 10 (2025): Vol 37 Issue 10, 2025

Abstract

This research focuses on synthesising an anticancer drug titled (E)-5-bromo-3-((3-chloro-4-fluorophenyl)imino)indolin-2-one (5BFIO) and validating its analytical values through theoretical and experimental evaluation using techniques such as FT-IR, FT-Raman, 1H and 13C NMR. Moreover, the anticancer activity of 5BFIO molecule was evaluated using molecular docking against cancer proteins (4B55, 5KYG and 6UGR) and 60 human cancer cell lines of NCI-60 under in silico and in vitro analyses, respectively. In the formation of docked complexes, low binding affinities -5.78 for 5BFIO-4B55, -6.72 for 5BFIO-5KYG and -8.86 for 5BFIO-6UGR) were noted in kcal/mol, respectively. Moreover, 5BFIO showed the best activity (49.59% GI) against the MCF7 breast cancer cell line. Density functional theory (DFT) was effectively employed to analyse the molecule’s stability under optimal conditions for comparative studies that incorporate both observational and computational data from gas phases. The outcomes of this study present a comprehensive analysis of gas-phase properties, including nonlinear optical (NLO) behaviour, molecular electrostatic potential (MEP), electron localization function (ELF), localized orbital locator (LOL) and reduced density gradient (RDG) descriptors. The pharmacological evaluation demonstrated significant anticancer activity and it could be derivatized into a more potent drug-like molecule using chemical reactions.

Keywords

Spectroscopic studies Electronic charge transfer Non-covalent interactions Molecular docking Cancer cell lines
(1)
Rekha, S.; Tamilselvan, S.; Asif, M.; Nasibullah, M.; Mishma, J. C.; Manikandan, P.; Kaleeswaran, S. Synthesis, Spectroscopic, Electronic Charge Transfer and Non-Covalent Interactions Studies on (E)-5-Bromo-3-(3-Chloro-4-fluorophenyl)imino)indolin-2-One: In Vitro Studies Against the Cancer Cell Lines. ajc 2025, 37, 2366-2378.
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