Novel Schiff Bases Based on the Quinolinone Skeleton: Syntheses, X-ray Structures and Fluorescent Properties
| Autor: | Roman Buchtík, Ivan Nemec, Zdeněk Trávníček |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization Magnetic Resonance Spectroscopy Stereochemistry 2-phenyl-3-amino-4(1H)-quinolinone Substituent Pharmaceutical Science Quantum yield Crystal structure Quinolones Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Schiff base lcsh:Organic chemistry in vitro cytotoxicity Spectroscopy Fourier Transform Infrared Drug Discovery Molecule Physical and Theoretical Chemistry Schiff Bases Molecular Structure Organic Chemistry Nuclear magnetic resonance spectroscopy Fluorescence Spectrometry Fluorescence chemistry Chemistry (miscellaneous) Molecular Medicine Quinine Sulfate fluorescence X-ray structures |
| Zdroj: | Molecules, Vol 19, Iss 9, Pp 13509-13525 (2014) Molecules Volume 19 Issue 9 Pages: 13509-13525 |
| ISSN: | 1420-3049 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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