Synthesis, characterization, spectroscopic studies and evaluation of toxicological effect on growth of wheat sprouts (Triticum aestivum) of new benzanthrone α-aryl-α-aminophosphonates

Maļeckis, Armands; Griškjāns, Evans; Cvetinska, Marija; Savicka, Marina; Belyakov, Sergey; Kirilova, Elena

doi:10.1016/j.molstruc.2022.134838

Cited by 4 publications

(3 citation statements)

References 43 publications

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“…Similar data were obtained for benzanthrone derivatives with the thiophene and unsubstituted phenyl group [ 2 ].…”

Section: Resultssupporting

confidence: 80%

“…In our prior investigation of α-aminophosphonates, we explored derivatives belonging to the anthrone dye family, specifically focusing on anthraquinone and benzanthrone derivatives [ 2 , 3 ]. These compounds, characterized by a donor–π–acceptor architecture, have attracted considerable attention owing to the noteworthy properties mentioned earlier.…”

Section: Introductionmentioning

confidence: 99%

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A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus

Maļeckis,

Cvetinska,

Kirjušina

et al. 2024

Molecules

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In this research, we explore the synthesis of and characterize α-aminophosphonates derived from anthraquinone and benzanthrone, focusing on their fluorescence properties and potential applications in confocal laser scanning microscopy (CLSM). The synthesized compounds exhibit notable solvatochromic behavior, emitting fluorescence from green to red across various solvents. Spectroscopic analysis, including 1H-, 13C-, and 31P-NMR, FTIR, and mass spectrometry, confirms the chemical structures. The compounds’ toxicity is evaluated using etiolated wheat sprouts, revealing varying degrees of impact on growth and oxidative damage. Furthermore, the study introduces these α-aminophosphonates for CLSM imaging of the parasitic flatworm Opisthorchis felineus, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights.

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“…Similar data were obtained for benzanthrone derivatives with the thiophene and unsubstituted phenyl group [ 2 ].…”

Section: Resultssupporting

confidence: 80%

Section: Introductionmentioning

confidence: 99%

A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus

Maļeckis,

Cvetinska,

Kirjušina

et al. 2024

Molecules

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“…Over the last few decades, 3-aminobenzanthrone derivatives (including alkylamines and imines [ 6 , 15 , 24 ], amides [ 25 , 26 , 27 ], amidines [ 28 ] and aminophosphonates [ 29 ]) have become the subject of significant attention. Among these many derivatives, substituted 3-piperazinyl derivatives of benzanthrone [ 30 , 31 ], as well as 3-(4-(diphenylamino)phenyl)benzanthrone and perylenediimide–benzanthrone dyads, were recently found to exhibit nonlinear optical (NLO) properties [ 32 , 33 ], which propels their design and use not only for imaging and sensing but also for applications in laser technology and optical communications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

Maļeckis,

Cvetinska,

Puckins

et al. 2023

Molecules

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In the present study, new fluorophores based on disubstituted benzanthrone derivatives were designed starting from 9-nitro-3-bromobenzanthrone with nucleophilic substitution of the bromine atom with some secondary cyclic amines. It has been found that this reaction is positively affected by the presence of a nitro group in comparison with 3-bromobenzanthrone. The new compounds exhibit intense absorption and pronounced luminescent properties in various organic solvents. In this regard, their photophysical properties were evaluated with an experimental study of the solvatochromic behavior of the obtained compounds in various solvents. It has recently been found that the addition of an electron-withdrawing nitro group to the benzanthrone core increases its first- and second-order hyperpolarizability. Such dyes can be used in the fabrication of optical limiter devices. Therefore, the developed fluorescent molecules have a potential prospect for extensive application in optoelectronics.

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Exploring Dual Solvatochromic Traits in Novel Fluorescent Benzanthrone Ethynyl Derivatives

Maļeckis,

Cvetinska,

Griškjāns

et al. 2024

J Solution Chem

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Synthesis, characterization, spectroscopic studies and evaluation of toxicological effect on growth of wheat sprouts (Triticum aestivum) of new benzanthrone α-aryl-α-aminophosphonates

Cited by 4 publications

References 43 publications

A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus

A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus

Synthesis and Properties of New 3-Heterylamino-Substituted 9-Nitrobenzanthrone Derivatives

Exploring Dual Solvatochromic Traits in Novel Fluorescent Benzanthrone Ethynyl Derivatives

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