New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity
Monika Kadela-Tomanek,
Maria Jastrzębska,
Ewa Bębenek,
Elwira Chrobak,
Małgorzata Latocha,
Joachim Kusz,
Dorota Tarnawska,
Stanisław Boryczka
Affiliations
Monika Kadela-Tomanek
Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
Maria Jastrzębska
Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
Ewa Bębenek
Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
Elwira Chrobak
Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
Małgorzata Latocha
Department of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 8 Jedności Str., 41-200 Sosnowiec, Poland
Joachim Kusz
Department of Physics of Crystals, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
Dorota Tarnawska
Silesian Center for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
Stanisław Boryczka
Department of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine in Sosnowiec, Medical University of Silesia in Katowice, 4 Jagiellońska Str., 41-200 Sosnowiec, Poland
Acetylenic 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.
