New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity
AbstractAcetylenic amine derivatives of the 5,8-quinolinedione were synthesized and characterized by the 1H and 13C 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 Δν 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 Δν. 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. View Full-Text
- Supplementary File 1:
PDF-Document (PDF, 5189 KB)
Share & Cite This Article
Kadela-Tomanek, M.; Jastrzębska, M.; Bębenek, E.; Chrobak, E.; Latocha, M.; Kusz, J.; Tarnawska, D.; Boryczka, S. New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity. Crystals 2017, 7, 15.
Kadela-Tomanek M, Jastrzębska M, Bębenek E, Chrobak E, Latocha M, Kusz J, Tarnawska D, Boryczka S. New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity. Crystals. 2017; 7(1):15.Chicago/Turabian Style
Kadela-Tomanek, Monika; Jastrzębska, Maria; Bębenek, Ewa; Chrobak, Elwira; Latocha, Małgorzata; Kusz, Joachim; Tarnawska, Dorota; Boryczka, Stanisław. 2017. "New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity." Crystals 7, no. 1: 15.
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.