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Публикации Черешнева В.А.
Публикации Чарушина В.Н.
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1.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Taniya O. S., Fedotov V. V., Sadieva L. K., Krinochkin A. P., Kovalev I. S., Kopchuk D. S., Zyryanov G. V., Ulomsky E. N., Rusinov V. L., Charushin V. N., Novikov A. S., Liu Y.
Заглавие : Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations
Место публикации : Dyes and Pigments. - 2022. - Vol. 204. - Ст.110405
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.
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2.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moseev T. D., Nikiforov E. A., Varaksin M. V., Starnovskaya E. S., Savchuk M. I., Nikonov I. L., Kopchuk D. S., Zyryanov G. V., Chupakhin O. N., Charushin V. N.
Заглавие : Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies
Место публикации : Synthesis. - 2021. - Vol. 53, № 19. - С. 3597-3607
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 2,2′-bipyridines--1,2,4-triazines--polyfluoroarenes
Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation.
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3.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moseev T. D., Lavrinchenko I. A., Varaksin M. V., Charushin V. N., Chupakhin O. N., Pobedinskaya D. Y., Demidov O. P., Borovlev I. V.
Заглавие : Meso-functionalization of calix[4]arene with 1,3,7-triazapyrene in the design of novel fluorophores with the dual target detection of Al3+ and Fe3+ cations
Место публикации : RSC Advances. - 2021. - Vol. 11, № 11. - С. 6407-6414
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A meso-functionalization strategy has successfully been applied to the synthesis of novel 1,3,7-triazapyrene derivatives of calixarenes. The key synthetic step in these transformations providing the direct C–C bond formation is nucleophilic substitution of hydrogen (SNH) in 1,3,7-triazapyrene. General photophysical characteristics for these macrocyclic compounds, as well as features in emission properties upon addition of various metal cations have been elaborated. Studies using NMR spectroscopy have also shown a mutual effect of both calix[4]arene and 1,3,7-triazapyrene moieties on the coordination process. The complex stoichiometry and binding constants for Al3+ and Fe3+ guests have been explored with titration experiments.
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4.

Вид документа : Статья из журнала
Шифр издания : Г/B 68
Автор(ы) : Akulov A. A., Varaksin M. V., Tsmokalyuk A. N., Charushin V. N., Chupakhin O. N.
Заглавие : Blue-light-promoted radical c-h azolation of cyclic nitrones enabled by selectfluor®
Место публикации : Green Chemistry. - 2021. - Vol. 23, № 5. - С. 2049-2057
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: An original approach to achieve the C(sp2)–H azolation of cyclic aldonitrones mediated by Selectfluor® has first been employed. By exploiting a metal-free, visible-light-promoted cross-dehydrogenative C–N coupling reaction between model aldonitrones, 2H-imidazole 1-oxides, and NH-containing azoles, a series of novel azaheterocyclic derivatives have been obtained in yields up to 94%. The elaborated protocol has proved to be appropriate for gram-scale processes and displayed potential for utilization in the synthesis of novel structural analogues of lanabecestat. Besides, mechanistic studies have revealed that this coupling reaction is likely to proceed via a nitroxide-involving radical pathway, encompassing a chain of electron transfer events, such as hydrogen atom transfer (HAT) and single electron transfer (SET).
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5.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Smyshliaeva L. A., Varaksin M. V., Fomina E. I., Medvedeva M. V., Svalova T. S., Kozitsina A. N., Charushin V. N., Chupakhin O. N., Demidov O. P., Borovlev I. V., Mensch C., Mampuys P., Maes B. U. W.
Заглавие : 1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties
Место публикации : Organometallics. - 2021. - Vol. 40, № 16. - С. 2792-2807
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.
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6.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moseev T. D., Nikiforov E. A., Varaksin M. V., Charushin V. N., Chupakhin O. N.
Заглавие : Metal-free C-H/C-H coupling of 2 H-imidazole 1-oxides with polyphenols toward imidazole-linked polyphenolic compounds
Место публикации : Journal of Organic Chemistry. - 2021. - Vol. 86, № 19. - С. 13702–13710
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The methodology of nucleophilic substitution of hydrogen (SNH) was successfully applied as a convenient synthetic tool to afford azaheterocyclic derivatives of phenols of various architectures. A series of 26 novel imidazole-linked polyphenolic compounds were first prepared in 72–95% yields through the direct metal-free C–H/C–H coupling of polyphenols with 2H-imidazole 1-oxides. Comprehensive studies on the reaction condition optimization, scope, and limitations enabled the development of a straightforward method toward novel bifunctional derivatives bearing both phenolic and imidazole scaffolds of particular interest in the design of challenging molecules for versatile applications in medicinal chemistry and materials science.
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7.

Вид документа : Статья из журнала
Шифр издания : Г/D 46
Автор(ы) : Gerasimova E. L., Gazizullina E. R., Borisova M. V., Igdisanova D. I., Nikiforov E. A., Moseev T. D., Varaksin M. V., Chupakhin O. N., Charushin V. N., Ivanova A. V.
Заглавие : Design and antioxidant properties of bifunctional 2H-imidazole-derived phenolic compounds-a new family of effective inhibitors for oxidative stress-associated destructive processes
Место публикации : Molecules. - 2021. - Vol. 26, № 21. - Ст.6534
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 2h-imidazole--polyphenols--antioxidant capacity--antiradical capacity
Аннотация: The synthesis of inhibitors for oxidative stress-associated destructive processes based on 2H-imidazole-derived phenolic compounds affording the bifunctional 2H-imidazole-derived phenolic compounds in good-to-excellent yields was reported. In particular, a series of bifunctional organic molecules of the 5-aryl-2H-imidazole family of various architectures bearing both electron-donating and electron-withdrawing substituents in the aryl fragment along with the different arrangements of the hydroxy groups in the polyphenol moiety, namely derivatives of phloroglucinol, pyrogallol, hydroxyquinol, including previously unknown water-soluble molecules, were studied. The structural and antioxidant properties of these bifunctional 5-aryl-2H-imidazoles were comprehensively studied. The redox transformations of the synthesized compounds were carried out. The integrated approach based on single and mixed mechanisms of antioxidant action, namely the AOC, ARC, Folin, and DPPH assays, were applied to estimate antioxidant activities. The relationship “structure-antioxidant properties” was established for each of the antioxidant action mechanisms. The conjugation effect was shown to result in a decrease in the mobility of the hydrogen atom, thus complicating the process of electron transfer in nearly all cases. On the contrary, the conjugation in imidazolyl substituted phloroglucinols was found to enhance their activity through the hydrogen transfer mechanism. Imidazole-derived polyphenolic compounds bearing the most electron-withdrawing functionality, namely the nitro group, were established to possess the higher values for both antioxidant and antiradical capacities. It was demonstrated that in the case of phloroglucinol derivatives, the conjugation effect resulted in a significant increase in the antiradical capacity (ARC) for a whole family of the considered 2H-imidazole-derived phenolic compounds in comparison with the corresponding unsubstituted phenols. Particularly, conjugation of the polyphenolic subunit with 2,2-dimethyl-5-(4-nitrophenyl)-2H-imidazol-4-yl fragment was shown to increase ARC from 2.26 to 5.16 (104 mol-eq/L). This means that the considered family of compounds is capable of exhibiting an antioxidant activity via transferring a hydrogen atom, exceeding the activity of known natural polyphenolic compounds.
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8.

Вид документа : Статья из сборника (однотомник)
Шифр издания :
Автор(ы) : Moseev T. D., Varaksin M. V., Virlova E. A., Chupakhin O. N., Charushin V. N.
Заглавие : Direct c-li/c-h coupling of c6f5li with azines and azoles n-oxides as efficient approach toward to polyfloorinated azaheterocycles
Место публикации : Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - С. 276-277
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): c-c coupling--nucleophilic substitution of hydrogen--fluorine--fluorarenes
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9.

Вид документа : Статья из сборника (однотомник)
Шифр издания :
Автор(ы) : Moseev T. D., Varaksin M. V., Lavrinchenko I. A., Chupakhin O. N., Charushin V. N.
Заглавие : Synthesis of meso-substituted calix[4]arenes via reaction of nucleophilic substitution of hydrogen (snh) in azine or azine-n-oxides
Место публикации : Actual problems of organic chemistry and biotechnology. - Екатеринбург, 2020. - С. 273-274
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): calix[4]arenes--azines--c-c coupling--nucleophilic substitution of hydrogen
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10.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Charushin V. N., Titova Y. A., Milaeva E. R.
Заглавие : Chemical elements in medicine
Место публикации : Herald of the Russian academy of sciences. - 2020. - Vol. 90, № 2. - С. 229-238
Ключевые слова (''Своб.индексиров.''): beta-lactam antibiotics--boron neutron capture therapy--fluoroquinolones--heterocycles
Аннотация: A brief review of chemical elements, compounds from which find application in medicine, ranging from the commonly occurring organogenic elements (carbon, hydrogen, nitrogen, oxygen, sulfur, and phosphorus), composing the structure of proteins and nucleic acids of the cells of living organisms and determining the genetic transmission, to native rarely encountered organic fluorine compounds, synthetic derivatives of which have become firmly ingrained in the arsenal of modern pharmaceutical drugs, is given. Strong emphasis is put on metalloproteins, which play a significant role in the biochemistry of vitally essential processes, as well as metal compounds that are widely used in medicine. Of particular importance are the chemical elements and the isotopes, compounds of which are employed in nuclear medicine for diagnostics and treatment of a wide range of diseases, oncological and cardiovascular in particular.
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