Crystal structure, spectroscopy, DFT, and thermal studies of 3-cyano-2(1H)-pyridones as potential anticancer agents.
RSC Adv
; 14(34): 24928-24941, 2024 Aug 05.
Article
em En
| MEDLINE
| ID: mdl-39135973
ABSTRACT
A series of 3-cyano-2(1H)-pyridones 4a-c were efficiently synthesized using an expeditious microwave-assisted multicomponent approach. Single-crystal XRD analysis revealed the presence of six independent molecules in the asymmetric unit cell for all compounds, with the crystal packing stabilized by a network of cyclic dimers formed by N-Hâ¯O[double bond, length as m-dash]C and C-Hâ¯O[double bond, length as m-dash]C intermolecular interactions. Additional supramolecular interactions, including C-Hâ¯π, C-Nâ¯π, and πâ¯π, and C-Hâ¯X (for halogenated derivatives, i.e., 4b and 4c), appear crucial for crystal stabilization. Density Functional Theory (DFT) calculations were employed to understand the electronic structures and potential binding affinities. Comprehensive spectroscopic characterization by FT-IR, UV-Vis, NMR, and HMRS techniques confirmed the structures of all synthesized compounds. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) were employed to evaluate the thermal stability of these compounds. The in vitro anticancer activity was evaluated against a panel of 60 human cancer cell lines, demonstrating promising activity against non-small-cell lung and breast cancer cell lines. Notably, compounds 4a and 4c exhibited the highest anticancer activity against the HOP-92 and MCF7 cell lines, with growth inhibition percentages (GI%) of 54.35 and 40.25, respectively.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
RSC Adv
Ano de publicação:
2024
Tipo de documento:
Article
País de publicação:
Reino Unido