title: Novel Schiff bases based on the quinolinone skeleton: syntheses, X-ray structures and fluorescent properties.
abstract: A series of a new type of Schiff bases 1-7, derived from 2-phenyl-3-amino-4(1H)-quinolinone and R-salicyladehyde derivatives wherein R = 3-hydroxy (1), 3,4-dihydroxy (2), 3-methoxy (3), 3-carboxy (4), 3-allyl (5), 5-chloro (6), and 5-nitro (7), was synthesized and structurally characterized. Each of the molecules 1, 3 and 7 consists of three planar moieties (i.e., a quinolinone and two phenyl rings), which are mutually oriented differently depending on the appropriate substituent R and the extent of non-covalent contacts stabilizing the crystal structures. The compounds were studied for their fluorescence properties, where compound 6 yielded the strongest intensity both in the solid phase and in 100 μM ethanol solution with a quantum yield of φ = 3.6% as compared to quinine sulfate used as a standard. The in vitro cytotoxicity of these compounds was tested against the human osteosarcoma (HOS) and breast adenocarcinoma (MCF7) cell lines, revealing no activity up to the concentration of 50 µM.
authors.affiliation: Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17 listopadu 12, CZ-77146 Olomouc, Czech Republic. zdenek.travnicek@upol.cz.
authors.forename: Zdeněk
authors.initials: Z
authors.lastname: Trávníček
authors.affiliation: Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17 listopadu 12, CZ-77146 Olomouc, Czech Republic. roman.buchtik@upol.cz.
authors.forename: Roman
authors.initials: R
authors.lastname: Buchtík
authors.affiliation: Regional Centre of Advanced Technologies and Materials, Department of Inorganic Chemistry, Faculty of Science, Palacký University, 17 listopadu 12, CZ-77146 Olomouc, Czech Republic. ivan.nemec@upol.cz.
authors.forename: Ivan
authors.initials: I
authors.lastname: Nemec
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D015363:Quinolones / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D015363:Quinolones; D012545:Schiff Bases