Photophysical properties of 7-hydroxyflavanone: Quantum chemical calculations and experimental studies

Wróblewski, Tomasz; Ushakou, Dzmitryi V.

doi:10.1016/j.saa.2019.02.092

Cited by 4 publications

(6 citation statements)

References 32 publications

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“…Pyridines are among the most important biochemical scaffolds with broader uses in the medicinal and pharmaceutical industries as well as intermediates in heterocyclic preparations . Among pyridine derivatives, dicyanopyridines act as ‘privileged skeleton’ owing to their prospective uses for therapy . These derivatives were recorded to serve as anti‐prion, human adenosine A2B receptor, antibacterial, anti‐cancer, and anti‐hepatitis B virus .…”

Section: Background and Originality Contentmentioning

confidence: 99%

“…More recently, we reported several ultrasonic‐assisted reactions strategies, which allow easy access to the construction of environmentally friendly‐ sustainable synthetic pathways for the preparation of various heterocycles . Computational chemistry, in the few decades, has become important for elucidating structures, mechanisms, molecular properties, and reaction selectivity . Herein we present for the first time an effective one‐pot method for the assembly of mono‐ and bis‐pyridine dicarbonitriles under US irradiation, through reacting selected ketones, HCl (generated in situ from oxaloyl chloride/MeOH) and tetracyanoethylene.…”

Section: Background and Originality Contentmentioning

confidence: 99%

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Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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of main observation and conclusion A highly efficient, simple, and clean single-step sonosynthetic procedure has been sophisticated for assembling new series of mono-and bis-pyridine dicarbonitriles from ketones, HCl, and tetracyanoethylene. The presented protocol is applicable for the preparation of a broad range of uniquely substituted pyridine dicarbonitriles and seems to be superior in comparison with other previously reported methods. The antiproliferative impact of the newly synthesized derivatives was screened towards three representative cancer cell lines (MCF-7, A549, and HCT116). Most of the evaluated derivatives showed a moderate to excellent anti-proliferative activity towards the selected cell lines. Of these, compounds 4h, 4k, 10, 12a, and 12b showed both potent anticancer activity (IC50<10 μM) and lower cytotoxic effect (IC50 > 58 μM) on non-tumorigenic cells (MCF-10A and NCM460), suggesting their promising potential to be lead molecules for future antitumor drug discovery. The structure-activity relationships have been also discussed. Moreover, quantum chemical studies based on Density Functional Theory (DFT) of the synthesized compounds were investigated and found to be consistent with the in vitro inhibitory activities. Results and DiscussionPreparation of 6-chloro-[2,2'-bipyridine]-4,5-dicarbonitrile (4a) by treatment of tetracyanoethylene (1, TCNE, 1.0 mmol), and 2-acetyl pyridine (2a, 1.0 mmol) with HCl (3.0 mL) was chosen as the template reaction (Scheme 1) under silent (70 o C) and ultra-502 www.cjc.wiley-vch.de

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Section: Background and Originality Contentmentioning

confidence: 99%

Section: Background and Originality Contentmentioning

confidence: 99%

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Arafa

Hussein

2020

Chin. J. Chem.

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“…Theoretical studies may provide very useful and, in many cases unavailable experimentally, information about the structure and properties of biomolecules. Among various theoretical methods, density functional theory (DFT) approach has been extensively used in the prediction of structure-related properties of flavanones and structurally similar compounds [14,15,16]. In particular it is possible to conclude about antioxidant activity of flavanones based on the analysis of the DFT predicted frontier orbitals and the DFT calculated quantum chemical descriptors [14].…”

Section: Introductionmentioning

confidence: 99%

“…It is well known that the type of solvent may affect UV–Vis spectra of chromophores, therefore, the incorporation of solvent effects is very important in the theoretical prediction of the absorption spectra. Polarizable Continuum Model (PCM) is the most frequently incorporated solvation model in theoretical studies of flavanones and chalcones structurally similar to the compounds under study [14,15]. The PCM model [27,28] is based on the assumption that solute is embedded in a shape-adapted cavity within solvent modelled as a dielectric continuum of defined dielectric constant.…”

Section: Introductionmentioning

confidence: 99%

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Position Impact of Hydroxy Groups on Spectral, Acid–Base Profiles and DNA Interactions of Several Monohydroxy Flavanones

et al. 2019

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Structure-related biological activities of flavanones are still considered largely unexplored. Since they exhibit various medicinal activities, it is intriguing to enter deeper into their chemical structures, electronic transitions or interactions with some biomolecules in order to find properties that allow us to better understand their effects. Little information is available on biological activity of flavanone and its monohydroxy derivatives in relation to their physicochemical properties as spectral profiles, existence of protonated/deprotonated species under pH changes or interaction with Calf Thymus DNA. We devoted this work to research demonstrating differences in the physicochemical properties of the four flavanones: flavanone, 2′-hydroxyflavanone, 6-hydroxyflavanone and 7-hydroxyflavanone and linking them to their biological activity. Potentiometric titration, UV–Vis spectroscopy were used to investigate influence of pH on acid–base and spectral profiles and to propose the mode of interaction with DNA. Cyclic voltammetry was applied to evaluate antioxidant potentiality and additionally, theoretical DFT(B3LYP) method to disclose electronic structure and properties of the compounds. Molecular geometries, proton affinities and pKa values have been determined. According to computational and cyclic voltammetry results we could predict higher antioxidant activity of 6-hydroxyflavanone with respect to other compounds. The values of Kb intrinsic binding constants of the flavanones indicated weak interactions with DNA. Structure–activity relationships observed for antioxidant activity and DNA interactions suggest that 6-hydroxyflavanone can protect DNA against oxidative damage most effectively than flavanone, 2′-hydroxyflavanone or 7-hydroxyflavanone.

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Scutellarein in organic solvents: changes in spectroscopic properties caused by solute-solvent interactions

Ushakou

Wróblewski

2022

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Photophysical properties of 7-hydroxyflavanone: Quantum chemical calculations and experimental studies

Cited by 4 publications

References 32 publications

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

Position Impact of Hydroxy Groups on Spectral, Acid–Base Profiles and DNA Interactions of Several Monohydroxy Flavanones

Scutellarein in organic solvents: changes in spectroscopic properties caused by solute-solvent interactions

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