Structural and spectroscopic properties of itraconazole and ketoconazole – Experimental and theoretical studies

Kujawski, Jacek; Czaja, Kornelia; Jodłowska-Siewert, Elżbieta; Dettlaff, Katarzyna; Żwawiak, Justyna; Kujawski, Radosław; Ratajczak, Tomasz; Bernard, Marek K.

doi:10.1016/j.molstruc.2017.05.128

Cited by 9 publications

(2 citation statements)

References 27 publications

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“…The study was complemented by comprehensive quantum chemistry computational analysis using density functional theory (DFT) [6][7] to predict the 1 H-NMR and 13 C-NMR spectroscopic properties of both the starting compounds and the resulting hybrids. To the best of our knowledge, this approach is common in the spectral identification and description of some APIs or newly synthesised compounds [8][9][10][11]. Additionally, in scientific literature, such information as computational data of NMR are only available for genistein ( 1 H-NMR and 13 C-NMR) [12][13] and flurbiprofen ( 13 C-NMR) [14], but for different computational methods than used in this study.…”

Section: Introductionmentioning

confidence: 99%

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Kossakowski,

Żwawiak,

Cherniienko

et al. 2024

Preprint

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Genistein (GEN) is one of the pharmaceutically valuable phenolic compounds, which belongs to the isoflavone group of flavonoids and is a natural phytohormone found mainly in soybeans and red clover. It affects estrogen receptors, functioning as a selective estrogen receptor modulator (SERM) with anti-inflammatory and antioxidant activity. The presence of reactive phenolic groups in genistein provides an opportunity to expand its structure by introducing components responsible for anti-inflammatory properties. Such an innovative combination of a compound with anticancer and antioxidant potential with an anti-inflammatory compound (NSAID) may lead to interesting new derivatives with dual mechanisms of biological action. The synthesis and characterisation of genistein-NSAID hybrid compounds (ibuprofen, ketoprofen, naproxen, flurbiprofen) was conducted, together with a comprehensive structural and quantum chemistry DFT (Density Functional Theory) computational analysis allowing the description of 1H-NMR and 13C-NMR spectroscopic properties of the starting compounds and the resulting hybrids. The study resulted in the formation of seven hybrid GEN-NSAID derivatives. In the case of ibuprofen, ketoprofen and flurbiprofen, a mixture of isomeric hybrid GEN-4’-NSAID and GEN-7-NSAID derivatives was obtained, whereas, for naproxen, only GEN-4’-NSAID was formed. The structural characteristics of the resulting compounds were determined using MS, IR, 1H-NMR and 13C-NMR spectroscopic methods. The most accurate DFT computational methods for predicting 1H-NMR and 13C-NMR spectra were also established with statistical parameters to assess their accuracy.

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Section: Introductionmentioning

confidence: 99%

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Kossakowski,

Żwawiak,

Cherniienko

et al. 2024

Preprint

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“…21 Imidazolidine ring is present in midazolam, phenytoin and ketoconazole that applied as anesthetic, anti-seizure and antifungal medicines. [22][23][24][25][26][27][28][29][30][31] In addition, antibacterial effect of synthetic imidazolidines were assessed on S. aureus, Pseudomonas aeruginosa and E. coli. 32,33 Antifungal, antimalarial, anticancer and anti-inflammatory activities were observed with compounds containing tetrahydropyrimidine core.…”

Section: Introductionmentioning

confidence: 99%

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

et al. 2020

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Background: Acinetobacter baumannii is a common infectious agent in hospitals. New antimicrobial agents are identified and prepared to combat these bacterial pathogens. In this context, the blocking potentials of a series of synthesized N-heterocyclic compounds, Cu/Fe3O4@SiO2 nanocomposites, glycine, poly-L-lysine, nisin and hydroalcoholic extracts of Trachyspermum ammi, Curcuma longa and green tea catechins were evaluated against non-resistant and multidrug-resistant strains of A. baumannii. Methods: Solutions of heterocyclic derivatives and hydroalcoholic extracts of Trachyspermum ammi, Curcuma longa and green tea catechins were prepared at initial concentration of 10240 μg ml-1 in 10% DMSO. Other compounds were dissolved in water at the same concentrations. Their in vitro inhibitory activity was assessed by determination of IZD, MIC and MBC values. Results: Glycine, poly-L-lysine, nisin, Curcuma longa and green tea catechins extracts, and thiazoles 3a, 3d and 3f were ineffective at their initial concentrations. Heterocyclic derivatives 7a-f, 3c, 3e and 3h, Cu/Fe3O4@SiO2 nanocomposites and Trachyspermum ammi extract could block the growth of bacterial strains with IZDs (7.40-15.51 mm), MICs (32-1024 µg ml-1) and MBCs (128-2048 µg ml-1). Conclusion: Among synthetic chemicals and natural products, the best antimicrobial effects were recorded with (E)-2-(5-acetyl-4-methylthiazol-2-yl)-2-(thiazolidin-2-ylidene)acetonitrile (7b) and the extract of Trachyspermum ammi. It is imperative that their toxic and histopathologic effects were assessed in future researches. It is predicted that the essential oil of Trachyspermum ammi will improve its antibacterial activities.

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3-Methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate:X-ray and computational study

Fizer

Slivka

Mariychuk

et al. 2018

Journal of Molecular Structure

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Structural and spectroscopic properties of itraconazole and ketoconazole – Experimental and theoretical studies

Cited by 9 publications

References 27 publications

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

3-Methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate:X-ray and computational study

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Structural and spectroscopic properties of itraconazole and ketoconazole – Experimental and theoretical studies

Cited by 9 publications

References 27 publications

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Molecular Insights into Genistein-NSAID Hybrids – Synthesis, Characterisation and DFT Study

Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe3O4@SiO2 Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii

3-Methylthio-4-phenyl-5-phenylamino-1,2,4-triazole hexabromotellurate:X-ray and computational study

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Comparative Evaluation of the Inhibitory Potential of Synthetic N-Heterocycles, Cu/Fe₃O₄@SiO₂ Nanocomposites and Some Natural Products against Non-Resistant and Antibiotic-Resistant Acinetobacter baumannii