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Crystals 2017, 7(1), 15; doi:10.3390/cryst7010015

New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

1
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
2
Department of Solid State Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
3
Silesian Center for Education and Interdisciplinary Research, University of Silesia, 75 Pułku Piechoty 1, 41-500 Chorzów, Poland
4
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
5
Department of Physics of Crystals, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
6
Department of Biophysics and Molecular Physics, Institute of Physics, University of Silesia, 4 Uniwersytecka Str., 40-007 Katowice, Poland
*
Author to whom correspondence should be addressed.
Academic Editor: Sławomir J. Grabowski
Received: 20 December 2016 / Revised: 2 January 2017 / Accepted: 4 January 2017 / Published: 7 January 2017
(This article belongs to the Section Interactions in Crystal Structures)
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Abstract

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. View Full-Text
Keywords: propargylamine-5,8-quinolinediones; crystal structure; H-bonding; IR carbonyl bands propargylamine-5,8-quinolinediones; crystal structure; H-bonding; IR carbonyl bands
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MDPI and ACS Style

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.

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