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Title: New acetylenic amine derivatives of 5,8-quinolinediones : synthesis, crystal structure and antiproliferative activity
Authors: Kadela-Tomanek, Monika
Jastrzębska, Maria
Bębenek, Ewa
Chrobak, Elwira
Latocha, Małgorzata
Kusz, Joachim
Tarnawska, Dorota
Boryczka, Stanisław
Keywords: propargylamine-5,8-quinolinediones; crystal structure; H-bonding; IR carbonyl bands
Issue Date: 2017
Citation: Crystals, Vol. 7, iss. 1 (2017), art. no. 15
Abstract: Acetylenic amine derivatives of the 5,8-quinolinedione were synthesized and characterized by the1H and13C NMR, IR spectroscopy and MS spectra. Additionally, the 6- and 7-substituted allylamine-5,8-quinolinediones were synthesized for comparison purposes. The crystal structure was determined for the 6-chloro-7-propargylamine-5,8-quinolinedione and 7-chloro-6-propargylamine-5,8-quinolinedione. Additionally, the IR spectral analysis supplemented by the density functional theory (DFT) calculations were carried out. It was found that different positions of the propargylamine side chain had a distinct influence on crystal structure, formation of H-bonds and the carbonyl stretching IR bands. Correlation between the frequency separation Δv of the carbonyl IR bands and the position of the 6- and 7-substituents was found. The 7-substituted derivatives exhibited a higher frequency separation Δv. The observed correlation could provide an opportunity to use the IR spectroscopy to study substitution reactions. Cytotoxic activities against three human cancer cell lines for the 5,8-quinolinedione derivatives with different amine substituents, i.e., propargylamine, N-methylpropargylamine, 1,1-dimethylpropargylamine, allylamine and propylamine were also analysed with respect to their molecular structure.
DOI: 10.3390/cryst7010015
ISSN: 2073-4352
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