Synthesis, crystal structure and infrared spectra of new 6- and 7-propylamine-5,8-quinolinediones

Jastrzębska, Maria; Boryczka, Stanisław; Kadela, Monika; Wrzalik, R.; Kusz, Joachim; Nowak, Maria

doi:10.1016/j.molstruc.2014.03.031

Cited by 18 publications

(26 citation statements)

References 22 publications

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“…In terms of bond distances and angles, the geometry of molecules 2a and 3a shows typical The selected values of bond distances and angles are presented in Table S1 (supplement material). In terms of bond distances and angles, the geometry of molecules 2a and 3a shows typical values [23,25]. These are in good agreement with the calculated values.…”

Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 86%

“…An angle between plane of rings and the propargylamine chain N2C9C10C11 is equal to 84.77 • . This conformation is very similar to that which occurred for the corresponding angle in the crystal structure of the 6-chloro-7-propylamine-5,8-quinolinedione (89.77 • ) described earlier by Jastrzebska et al [25]. Figure 2 depicts the hydrogen bonds found in the crystal structure of 2a.…”

Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 84%

“…An angle between the 5,8-quinolinedione rings' plane and the propargylamine chain is equal to 68.57° and is significantly smaller than that for 2a (84.77°). Simultaneously, this angle is very similar to the corresponding angle in the crystal structure of the 7-chloro-6-propylamine-5,8-quinolinedione 3e (68.57°), which was described earlier [25]. Figure 3 shows the unit cell and the hydrogen bonds identified in the crystal structure of 3a.…”

Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 83%

“…It can create the opportunity for additional structural investigations using IR carbonyl bands. For example, we recently found an interesting correlation between the frequency separation of carbonyl bands and the position of propylamine substituents on 5,8-quinolinediones [25]. Therefore, in this report we also aimed to check whether a similar correlation exists for the propargylamine-substituted 5,8-quinolinediones.…”

Section: Introductionmentioning

confidence: 78%

“…The 6,7-dichloro-5,8-quinolinedione 1 was prepared by the oxidation of the 8-hydroxyquinoline [12] and used as a starting compound for the synthesis of the acetylenic derivatives 2-3 using procedures described in the literature [8,9,25]. Treatment of compound 1 with the corresponding amine in tetrahydrofuran in the presence of potassium carbonate at room temperature gave a mixture of 7-and 6-aminosubstituted derivatives, 2a-e and 3a-e, respectively (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

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

et al. 2017

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Acetylenic amine derivatives of the 5,8-quinolinedione were synthesized and characterized by the 1 H and 13 C 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 ∆ν 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 ∆ν. 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.

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Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 86%

Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 84%

Section: Crystal Structure and Formation Of Hydrogen Bondssupporting

confidence: 83%

Section: Introductionmentioning

confidence: 78%