Structural, vibrational and quantum chemical investigations for 6,7-dichloro-2-methyl-5,8-quinolinedione. Cytotoxic and molecular docking studies

Publication date: 15 September 2018 Source:Journal of Molecular Structure, Volume 1168 Author(s): Monika Kadela-Tomanek, Bartosz Pawełczak, Maria Jastrzębska, Ewa Bębenek, Elwira Chrobak, Małgorzata Latocha, Joachim Kusz, Maria Książek, Stanisław Boryczka 6,7-Dichloro-2-methyl-5,8-quinolinedione was investigated using different experimental methods as well as a variety of various quantum chemical calculations in order to characterize its molecular structure as a potential anticancer active compound. We used X-ray diffraction, IR spectrum analysis supplemented by the density functional theory (DFT) calculations, molecular electrostatic potential (MEP) and molecular orbital (HOMO, LUMO) analyses. The analyzes were carried out with respect to 6,7-dichloro-5,8-quinolinedione. It was found that introduction of the methyl group at the C-2 position distinctly affected the crystal structure, formation of H-bonds and the carbonyl stretching IR bands of the title compound. The molecular electrostatic potential map showed how the electrophilic and nucleophilic regions are located in the molecule. The intra- and intermolecular bonding and interaction between bonds were interpreted using the Natural Bond Orbital (NBO) and Natural Localized Molecular Orbital (NLMO) analysis. The title compound was tested for its anticancer activity in vitro against the several human cancer cell lines. 6,7-Dichloro-2-methyl-5,8-quinolinedione showed a higher cytotoxic activity against can...
Source: Journal of Molecular Structure - Category: Molecular Biology Source Type: research