Synthesis, Structure and Cytotoxic Activity of Mono- and Dialkoxy Derivatives of 5,8-Quinolinedione

Kadela, Monika; Jastrzębska, Maria; Bębenek, Ewa; Chrobak, Elwira; Latocha, Małgorzata; Kusz, Joachim; Książek, Maria; Boryczka, Stanisław

doi:10.3390/molecules21020156

Cited by 19 publications

(22 citation statements)

References 22 publications

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“…According to the literature data [8,12], such differentiation is possible when using the 13 C NMR spectra. It was found that the isomers 2 and 3 showed different signal intensities of the C-5, C-8, C-6 and C-7 atoms.…”

Section: Chemistrymentioning

confidence: 99%

“…Synthesis was carried out using the procedure previously described by Kadela et al [8,9,25]. Briefly, the 6,7-dichloro-5,8-quinolinedione 1 (0.1 g, 0.441 mmol) was dissolved in dry tetrahydrofuran (1 mL).…”

Section: Chemistrymentioning

confidence: 99%

“…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%

“…For example, it was found that substitution of the electron-withdrawing groups at the 6-or 7-positions of the 5,8-quinolinedione led to an increase in the DNA degradation [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

“…The 5,8-quinolinedione derivatives were among the first compounds to be systematically modified in order to find products with higher biological activities, such as anticancer, anti-inflammatory or antibacterial [1][2][3][4][5][6][7][8][9]. For example, it was found that substitution of the electron-withdrawing groups at the 6-or 7-positions of the 5,8-quinolinedione led to an increase in the DNA degradation [8][9][10][11][12][13].…”

Section: Introductionmentioning

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: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

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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Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Yilmaz Goler,

Tarbin Jannuzzi,

Biswas

et al. 2023

Chemistry & Biodiversity

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In an effort to develop potent and secure antiproliferative lead compounds, five quinolinequinones (AQQ1‐5) described previously have been selected and submitted to the National Cancer Institute (NCI) of Bethesda. Four of five quinolinequinones (AQQ2‐5) were selected for five‐dose screening and they displayed promising antiproliferative effects against several cancer types. All AQQs showed a super anticancer profile with low micromolar GI50 and TGI values against most cell lines. AQQ2‐5 reduced the proliferation of all some cell lines at a single dose and five additional doses. We investigated the in vitro cytotoxic activities of the most promising compounds, AQQ2 and AQQ3. Concomitantly, IC50 values of AQQ2 against MCF7 and T‐47D cell lines of breast cancer, DU‐145 cell line of prostate cancer, HCT‐116 cell line of colon cancer, and HaCaT human keratinocytes were determined. AQQ2 exhibited anticancer activity through the induction of apoptosis and caused alterations in the cell cycle. In silico pharmacokinetic studies of all analogs have been carried out against ATR, CHK1, WEE1, CDK1, and CDK2. In addition to this, in vitro ADME and in vivo pharmacokinetic profiling for the most effective AAQ (AAQ2).

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Design, synthesis and biological activity of 1,4-quinone moiety attached to betulin derivatives as potent DT-diaphorase substrate

Kadela-Tomanek

Jastrzębska

Marciniec

et al. 2021

Bioorganic Chemistry

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Synthesis, Structure and Cytotoxic Activity of Mono- and Dialkoxy Derivatives of 5,8-Quinolinedione

Cited by 19 publications

References 22 publications

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

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

Analysis of Quinolinequinone Analogs with Promising Cytotoxic Activity against Breast Cancer

Design, synthesis and biological activity of 1,4-quinone moiety attached to betulin derivatives as potent DT-diaphorase substrate

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