U 92 Utepova, I. A. Azinylferrocenes: synthesis and properties [Text] / I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Heterocycles. - 2008. - Vol. 76, № 1. - P39-72 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
T 44 The C-C coupling of ferrocenes with electron-deficlent azaaromatics - a new route for construction of heterocyclic ligands and complexes [] / O. N. Chupakhin, I. S. Kovalev, I. A. Utepova, V. L. Rusinov, V. N. Charushin // 20-th International Congress of Heterocyclic Chemistry, Palermo, July 31-August 5, 2005 : book of abstracts . - Palermo, Italy, 2005. - С. 507. - Библиогр.: с. 507 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
P 17 Palladium(II)-Catalyzed Oxidative C–H/C–H Coupling and Eliminative SNH Reactions in Direct Functionalization of Imidazole Oxides with Indoles / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Journal of Organic Chemistry. - 2012. - Vol.77, №20. - С. 9087-9093 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): IMIDAZOLE OXIDES -- INDOLES Аннотация: Two novel synthetic approaches to realize the direct C(sp2)–H bond functionalization in cyclic nitrones are reported. Palladium(II)-catalyzed oxidative C–C coupling of 2,2-dialkyl-4-phenyl-2H-imidazole 1-oxides with indoles was shown to result in the formation of 5-indolyl-3-yl derivatives, while nucleophilic substitution of hydrogen (SNH) at C(5) of the same imidazole system was found to afford the corresponding deoxygenated compounds \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2010, v.77, p.9087.pdf |
S 98 Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions? [Electronic resource] / A. A Musikhina, I. A. Utepova, N. S. Serebryakov, O. N. Chupakhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1191-1194. - Bibliogr. : p. 1194 (28 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENYLAZINES -- NEGISHI Аннотация: Preparation of new hetaryl-containing planar chiral ferrocene by a nucleophilic substitution of hydrogen in azines was performed using a lithium derivative of (S)-ferrocenyl-p-tolylsulfoxide as s nucleophilic reagent \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1191-1194.pdf |
S 98 Synthesis of new meso-substituted heterocyclic calix[4]arenes via SN H approach [Electronic resource] / M. V. Varaksin, I. A. Utepova, G. N. Chupakhin, V. N. Charushin // Macroheterocycles . - 2013. - Vol.6, №4. - С. 308-314. - Bibliogr. : p. 313-314 (42 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- C-C COUPLING -- CALIX[4]ARENES Аннотация: An effective synthetic approach to heterocyclic derivatives of meso-substituted calixarenes has been suggested by using the SN H methodology based on the direct, non-catalyzed by transition metals, C-C coupling of 1,2,4-triazines with the lithium salts of tetramethoxycalix[4]arenes \\\\expert2\\NBO\\Macroheterocycles\\2013.6.4.308-314.pdf |
S 10 S-N(H) Approach in the Synthesis of meso-Substituted Heterocyclic Calix[4]arenes / K. A. Khlamkin, M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Уральский научный форум "Современные проблемы органической химии". XVII Молодежная школа-конф. по органической химии, Екатернинбург, 8-12 июня 2014 г. : сб. тез. - Екатеринбург, 2014. - С. 236. - Bibliogr. : p. 236 (4 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HETEROCYCLES -- HETEROCYCLIC COMPOUNDS -- CALIXARENES |
D 62 Direct Nucleophilic Functionaliation of Arines and their N-Oxidesby Lithiumaldonitrones / S. V. Mikhaylov, M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Уральский научный форум "Современные проблемы органической химии". XVII Молодежная школа-конф. по органической химии, Екатернинбург, 8-12 июня 2014 г. : сб. тез. - Екатеринбург, 2014. - С. 238. - Bibliogr. : p. 238 (3 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINES -- LITHIUMALDONITRONES -- HETEROCYCLIC COMPOUNDS |
T 44 The synthesis of planar chiral ferrocenes and their use for an effective asymmetric catalysis / O. N. Chupakhin, I. A. Utepova, V. N. Charushin, A. A Musikhina, P. O. Serebrennikova // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - Marseille, France, 2013. - С. 224 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENES -- EFFECTIVE ASYMMETRIC CATALYSIS |
D 62 Direct C(sp2)-H Bond Functionalization in Cyclic Aldonitrones: Palladium(II)-Catalyzed Oxidative Cross-Coupling and Eliminative SNH Reactions / M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, S. V. Mikhaylov, I. A. Utepova, B. A. Trofimov // 18th European Symposium on Organic Chemistry ESOC-2013, Marseille, France, 7-12 July 2013 : book of abstracts. - Marseille, France, 2013. - С. 329 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PALLADIUM(II) -- SNH REACTIONS -- CYCLIC ALDONITRONES |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |
D 62 Direct nuclophilic C-H functionalization of azines and their N-oxides by lithium derivatives of aldonitrones [Electronic resource] / M. V. Varaksin, I. A. Utepova, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2015. - Vol. 71, №38. - С. 7077-7082. - Bibliogr. : p. 7082 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DIPOLE-STABILIZED CARBANIONS -- ORGANIC-SYNTHESIS -- CHEMICAL-PROPERTIES; Аннотация: Novel ligands of the azine family for complexing with metals have been obtained as a result of the uncatalyzed C-C coupling reactions of quinoline, quinoxaline, 1,10-phenantroline, and their N-oxides with (1-oxido-3-phenyl-1,4-diazaspiro[4.5]deca-1,3-dien-2-yl)lithium \\\\expert2\\nbo\\Tetrahedron\\2015, v. 71 , p. 7077-7082.pdf |
A 23 Aerobic oxidative C-H/C-H coupling of azaaromatics with indoles and pyrroles in the presence of TiO2 as a photocatalyst [Electronic resource] / I. A. Utepova, M. A. Trestsova, O. N. Chupakhin, V. N. Charushin, A. A. Rempel // Green Chemistry. - 2015. - Vol. 17, № 8. - С. 4401-4410. - Bibliogr. : p. 4409-4410 (30 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BOND ACTIVATION -- INHIBITORS -- HYDROGEN Аннотация: In this paper we wish to report a highly selective and benign method for the double C-H/C-H coupling of azaaromatics with indoles or pyrrole in the presence of air oxygen/TiO2, as an effective photocatalytic oxidative system. It has been shown that this versatile approach can be applied for direct C-H functionalisation of a variety of azaaromatic systems, such as mono-, di- and triazines, substituted and unsubstituted azines and their benzo-annelated analogues. \\\\expert2\\nbo\\Green Chemistry\\2015, v.17, N 8, p.4401-4410.pdf |
Methodology of C(sp2)-H functionalization in mono- and diazine N-oxides in the synthesis of heterocyclic meso-substituted calixarenes [Electronic resource] / M. V. Varaksin, O. N. Chupakhin, V. N. Charushin, K. A. Khlamkin, I. A. Utepova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 6, № 5. - С. 1093-1096 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): MESO-SUBSTITUTED CALIXARENES -- MESO-SUBSTITUTED AZINYLCALIXARENES -- METAL CATALYSIS Аннотация: Earlier unknown meso-substituted azinylcalixarenes were obtained by a direct cross-coupling of 2-lithium-25,26,27,28-tetramethoxycalix[4]arenes with mono- and diazine N-oxides without transition metal catalysis. \\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 64 (5), 1093-1096.pdf |
T 82 Transition metal-free regioselective cross-coupling of azine N-oxides with cymantrenyl lithium / A. A. Musikhina, I. A. Utepova, O. N. Chupakhin, V. N. Charushin, P. A. Slepukhin // Journal of organometallic chemistry. - 2018. - Vol. 870 . - P32-37 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZINE-N-OXIDES -- CYMANTRENE -- C-C COUPLING -- NUCLEOPHILE Аннотация: The facile C–C coupling reaction of activated forms of azaaromatics (azine-N-oxides) with cymantrenyl lithium, as a nucleophile, has first been carried out. It has been established that aromatization of intermediate adducts can be realized through either oxidative or eliminative pathways, depending on the structure of the starting azine N-oxide. In particular, the dihydroazinyl intermediates, bearing the additional N(4)-atom relative to the N-oxide group, proved to undergo aromatization through the eliminative pathway. The X-ray studies of 3,6-diphenyl-1,2,4-triazine-5-yl-cymantrene have revealed that it is crystallized in both orthorhombic and monoclinic forms. |
T 82 Transition metal-free regioselective cross-coupling of azine N-oxides with cymantrenyl lithium / A. A Musikhina, A. V. Kostromina, E. Y. Zyryanova, I. A. Utepova, O. N. Chupakhin, V. N. Charushin, P. A. Slepukhin // Современные синтетические методологии для создания лекарственных препаратов и функциональных материалов (MOSM2018): вторая международная научно-практическая конференция : материалы и доклады. - Екатеринбург, 2019. - С. 147 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
Pyrrolylquinoxaline-2-one derivative as a potent therapeutic factor for brain trauma rehabilitation / E. A. Dutysheva, M. A. Mikeladze, N. D. Aksenov [и др.] // Pharmaceutics. - 2020. - Vol. 12, № 5. - С. 414 Кл.слова (ненормированные): APOPTOSIS -- CEREBROSPINAL FLUID -- HSP70 -- SMALL MOLECULE -- TRAUMATIC BRAIN INJURY Аннотация: Traumatic brain injury (TBI) often causes massive brain cell death accompanied by the accumulation of toxic factors in interstitial and cerebrospinal fluids. The persistence of the damaged brain area is not transient and may occur within days and weeks. Chaperone Hsp70 is known for its cytoprotective and antiapoptotic activity, and thus, a therapeutic approach based on chemically induced Hsp70 expression may become a promising approach to lower post-traumatic complications. To simulate the processes of secondary damage, we used an animal model of TBI and a cell model based on the cultivation of target cells in the presence of cerebrospinal fluid (CSF) from injured rats. Here we present a novel low molecular weight substance, PQ-29, which induces the synthesis of Hsp70 and empowers the resistance of rat C6 glioma cells to the cytotoxic effect of rat cerebrospinal fluid taken from rats subjected to TBI. In an animal model of TBI, PQ-29 elevated the Hsp70 level in brain cells and significantly slowed the process of the apoptosis in acceptor cells in response to cerebrospinal fluid action. The compound was also shown to rescue the motor function of traumatized rats, thus proving its potential application in rehabilitation therapy after TBI. |
Dataset of NMR-spectra pyrrolyl- and indolylazines and evidence of their ability to induce heat shock genes expression in human neurons / E. A. Dutysheva, I. A. Utepova, M. A. Trestsova [et al.] // Data in Brief. - 2021. - № 39. - P107562 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRROLYLAZINES -- INDOLYLAZINES -- PHOTOCATALYSIS -- NUCLEAR MAGNETIC RESONANCE -- GREEN CHEMISTRY Аннотация: These data are related to our previous paper “Synthesis and approbation of new neuroprotective chemicals of pyrrolyl-and indolylazine classes in a cell model of Alzheimer’s disease” (Dutysheva et al., 2021), in which we demonstrate neu-roprotective abilities of pyrrolyl- and indolylazines in a cell model of Alzheimer’s disease. Using a novel procedure of photocatalysis we have synthesized a group of new compounds. The current article presents nuclear magnetic resonance spectra including heteronuclear single quantum coherence spectra of chemicals synthesized by us. The effect of new compounds have on heat shock proteins genes expression in reprogrammed human neurons are presented. We also presented data that verify neuronal phenotype of reprogrammed cells. |
Synthesis and approbation of new neuroprotective chemicals of pyrrolyl- and indolylazine classes in a cell model of Alzheimer's disease / E. A. Dutysheva, I. A. Utepova, M. A. Trestsova [et al.] // European journal of medicinal chemistry. - 2021. - Vol. 222. - P113577 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): PYRROLYLAZINES -- NEUROPROTECTORS -- CHAPERONES -- AMYLOID-BETA -- ALZHEIMER'S DISEASE Аннотация: One of the major causes of neurodegeneration in the pathogenesis of Alzheimer's disease is the accumulation of cytotoxic amyloid species within the intercellular compartments of the brain. The efficacy of the anti-proteotoxic mechanism based on the molecular chaperones Hsp70 and Hsp90 in numerous types of neurons is often low, while its pharmacological enhancement has been shown to ameliorate the physiological and cognitive functions of the brain. Suggesting that the chemicals able to induce heat shock protein synthesis and therefore rescue neural cells from cytotoxicity associated with amyloid, we have synthesized a group of pyrrolyl- and indolylazines that cause the accumulation of heat shock proteins, using a novel method of photocatalysis that is employed in green chemistry. The selected compounds were tested in a cell model of Alzheimer's disease and demonstrated a pronounced neuroprotective effect. These substances increased the survival of neurons, blocked the activation of β-galactosidase, and prevented apoptosis in neurons cultured in the presence of β-amyloid. |
Synthesis and properties of azines functionalized graphene with extremely high adsorptive ability to Eu3+ ions / O. N. Chupakhin, A. A Musikhina, I. A. Utepova [et al.] // Flatchem. - 2022. - Vol. 33. - P100348 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In this work, a versatile synthetic protocol for obtaining of new promising carbon materials based on the C–C coupling of graphenide lithium species with azaaromatic compounds (1,10-phenanthroline, phenyl-1,2,5-oxadiazolo[3,4-b]pyrazine) has been suggested. It was shown that more electrophilic oxadiazolopyrazine gave the product with high degree of graphene functionalization and demonstrated non-isomorphic properties. At the same time, phenanthrolinyl graphene has less functionalization degree due to a lower electrophilicity of azine. However, the large size of pores between organic residues in phenanthrolinyl graphene allows adsorbing almost 10% of Eu3+. The mesurment of adsorption isotherm showed an extremely high affinity of phenanthrolinylgraphene to Eu (III) ions in netural or alkaline conditions, and the obtained hybrid material could work at least 5 sorption/desorption cycles. The structures of azine-graphene dyads were verified by complex of modern physicochemical analyses methods (the Raman spectroscopy, FTIR, XPS, SEM, EDS and TGA analyses). |