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1.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and Antitubercular Evaluation on Novel 1-Ethyl-5-(hetero)aryl- 1,6-dihydropyrazine-2,3-dicarbonitriles and 3-Cyano-1-ethyl-5-(hetero) aryl-2(1H)-pyrazinones / M. A. Kravchenko, E. V. Verbitskiy, S. N. Skornyakov, P. A. Slepukhin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Anti-Infective Agents. - 2016. - Vol. 14, № 2. - С. 139-144
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRAZINES -- ANTITUBERCULOSIS ACTIVITY -- 2(1H)-PYRAZINONE
Аннотация: A simple method based on hydrolysis of 2,3-dicyanopyrazinium salts has been used for the synthesis of the corresponding 5-(hetero)aryl-3-cyano-1-ethyl-2(1H)-pyrazinones. Also, the series of novel 1-ethyl-5-(hetero)aryl-1,6-dihydropyrazine-2,3-dicarbonitriles have been obtained through reduction of the same pyrazinium salts with triethylsilane. The obtained compounds proved to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, Mycobacterium avium, Mycobacterium terrae, as well as against rifampicin and isoniazid-resistance strains of Mycobacterium tuberculosis. The data for acute in vivo toxicity in mice have been obtained for these compounds which appear to be promising antitubercular agents

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2.
Инвентарный номер: нет.
   
   N 52

   
    New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, M. Z. Shafikov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and Pigments. - 2016. - Vol. 137. - С. 360-371. - Bibliogr. : p. 370-371 (50 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
4,5-DI(HETERO)ARYLPYRIMIDINES -- NITROAROMATIC EXPLOSIVES -- VAPOR PHASE
Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs.

\\\\expert2\\nbo\\Dyes and Pigments\\2016, v. 137, p.360-371.pdf
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3.
Инвентарный номер: нет.
   
   C 51

   
    Chemoenzymatic Synthesis of Modified 2′-Deoxy-2′-fluoro-β-d-arabinofuranosyl Benzimidazoles and Evaluation of Their Activity Against Herpes Simplex Virus Type 1 / M. I. Kharitonova, K. V. Antonov, I. V. Fateev, M. Ya. Berzina, S. K. Kotovskaya, V. N. Charushin // Synthesis (Germany). - 2017. - Vol. 49, № 5. - С. 1043-1052
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHEMOENZYMATIC SYNTHESIS -- BENZIMIDAZOLES -- HERPES SIMPLEX VIRUS TYPE 1
Аннотация: 1-(2′-Deoxy-2′-fluoro-β-d-arabinofuranosyl)benzimidazoles containing 4,6-difluoro-, 4,5,6-trifluoro-, 5-fluoro-6-methoxy-, and 5-methoxy-4,6-difluorobenzimidazole fragments were synthesized by using purine nucleoside phosphorylase-catalyzed chemoenzymatic approach. As expected, enzymatic synthesis of nucleosides proceeds in lower yields of target compounds in comparison with the synthesis of ribo- and 2′-deoxyribobenzimidazoles (40–55% vs 60–90%). The compounds obtained were tested against the herpes simplex virus type 1, by using the Vero E6 cells. 5-Methoxy-4,6-difluoro-1-β-d-(2′-deoxy-2′-fluoroarabinofuranosyl)benzimidazole did not show any antiviral activity, when used in nontoxic concentration. All other nucleosides proved to exhibit a selective antiherpes activity. In contrast, it was shown that benzimidazole-β-d-arabinofuranosides of both di- and trisubstituted derivatives, having substituents in positions 4–6 of the benzene ring, as well as unsubstituted compounds, cannot be synthesized by enzymatic transglycosylation. 1-(β-d-Arabinofuranosyl)benzimidazole was obtained through glycosylation of N-trimethylsilylbenzimidazole with 1-chloro-2,3,5-O-methoxymethyl-d-arabinose. The behavior of this compound, as inhibitor of purine nucleoside phosphorylase (PNP) E. сoli, was investigated. 1-(β-d-Arabinofuranosyl)benzimidazole was found to belong to a mixed type of inhibitors of PNP. This fact explains why all attempts to perform enzymatic arabinosylation of 4,6-di-, 5,6-di-, and 4,5,6-trisubstituted benzimidazoles failed

\\\\expert2\\NBO\\Synthesis\\2017, v. 49(5), p. 1043-1052.pdf
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4.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis and Evaluation of Novel [1,2,4]Triazolo[5,1-c][1,2,4]-triazines and Pyrazolo[5,1-c][1,2,4]triazines as Potential Antidiabetic Agents / V. L. Rusinov, I. M. Sapozhnikova, A. M. Bliznik, O. N. Chupakhin, V. N. Charushin, A. A. Spasov, P. M. Vassiliev, V. A. Kuznetsova, A. I. Rashchenko, D. A. Babkov // Archiv der Pharmazie. - 2017. - Vol. 350, № 5. - Pe1600361-[1]-e1600361-[15]
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ANTIDIABETIC AGENTS -- ANTIGLYCATION -- AZOLOTRIAZINES -- CROSS-LINK BREAKERS -- DIABETES MELLITUS -- DIPEPTIDYL PEPTIDASE-4 INHIBITORS
Аннотация: Inhibition of the dipeptidyl peptidase-4 (DPP4) enzyme activity and prevention of advanced glycation end (AGE) products formation represents a reliable approach to achieve control over hyperglycemia and the associated pathogenesis of diabetic vascular complications. In the frames of this research study, several triazolo- and pyrazolotriazines were synthesized and evaluated as inhibitors of AGE products formation, DPP4, glycogen phosphorylase and α-glucosidase activities, as well as AGE cross-link breakers. From the two considered classes of heterocyclic compounds, the pyrazolotriazines showed the highest potency as antiglycating agents and DPP4 inhibitors. Structure–activity relationships (SAR) for these compounds, which can be considered as potential drugs for the treatment of type 2 diabetes, were evaluated.

\\\\Expert2\\NBO\\Archiv der Pharmazie\\2017 V 350 P.pdf
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5.
Инвентарный номер: нет.
   
   N 52

   
    New modified 2-aminobenzimidazole nucleosides: Synthesis and evaluation of their activity against herpes simplex virus type 1 / M. I. Kharitonova, A. O. Denisova, A. L. Kayushin, I. D. Konstantinova, A. I. Miroshnikov, S. K. Kotovskaya, V. N. Charushin, V. L. Andronova, G. A. Galegov // Bioorganic and Medicinal Chemistry Letters. - 2017. - Vol. 27, № 11. - P2484-2487
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ANTIVIRAL ACTIVITY -- BENZIMIDAZOLES -- FLUORINATED COMPOUNDS -- NUCLEOSIDE PHOSPHORYLASES -- NUCLEOSIDES -- TRANSGLYCOSYLATION REACTION
Аннотация: Using the enzymatic transglycosylation reaction β-d-ribo- and 2′-deoxyribofuranosides of 2-amino-5,6-difluorobenzimidazole nucleosides have been synthesized. 2-Amino-5,6-difluoro-benzimidazole riboside proved to exhibit a selective antiviral activity (selectivity index >32) against a wild strain of the herpes simplex virus type 1, as well as towards virus strains that are resistant to acyclovir, cidofovir, and foscarnet. We believe that this compound might be used for treatment of herpes infections in those cases, when acyclovir is not efficient.

\\\\Expert2\\NBO\\Bioorganic and Medicinal Chemistry Letters\\2017 v.27 p.2484-2487.pdf
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6.
Инвентарный номер: нет.
   
   N 52

   
    New 4,5-di(hetero)arylpyrimidines as sensing elements for detection of nitroaromatic explosives in vapor phase / E. V. Verbitskiy, A. A. Baranova, K. I. Lugovik, K. O. Khokhlov, E. M. Cheprakova, M. Z. Shafikov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Dyes and Pigments. - 2017. - Vol. 137. - P360-371
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
FLUORESCENCE QUENCHING -- NITROAROMATIC EXPLOSIVES -- TRIPHENYLAMINES -- CARBAZOLES -- PYRIMIDINES
Аннотация: A series of D–π–A–π–D type dyes based on pyrimidines, bearing thiophene linkers, have been studied as sensing fluorophores. Fluorescence studies have demonstrated that the emission of all derivatives is sensitive to the presence of 2,4,6-trinitrotoluene (TNT) and other nitroaromatic compounds (NACs), in their acetonitrile solutions. The detection limits of fluorophores to NACs proved to be in the range from 10−4 to 10−6 mol/L. The time-resolved fluorescence measurements and theoretical investigation into the quenching mechanism in the presence of fluorophore has been performed. The two types of sensor prototypes for handheld sniffer «Nitroscan» (Plant «Promautomatika», Ekaterinburg, Russia) on the basis of non-woven dry wipe and spunlace non-woven fabric with various quantities of the most sensitive fluorophore have been fabricated. The reusable, reversible and sensitive response of the designed prototypes to NACs enables one to qualify these compounds as promising fluorescent sensory materials for detection of NACs.

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7.
Инвентарный номер: нет.
   
   D 62

   
    Direct CC coupling of phthalazine-N-oxide with the carboranyl anion - An original approach to C-modification of carboranes / M. V. Varaksin, L. A. Galliamova, O. A. Stepanova, O. S. Eltsov, O. N. Chupakhin, V. N. Charushin // Journal of Organometallic Chemistry. - 2017. - Vol. 830. - P93-99
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CARBORANES -- C-C COUPLING -- PHTHALAZINE-N-OXIDE
Аннотация: An original transition metal-free approach based on the direct CC coupling of phtalazine-N-oxide with the carboranyl anion has been developed. A series of the novel C-modified closo-carboranes such as 1-(2-oxido-3-acyl-3,4-dihydrophtalazinyl-4-yl)-1,2-dicarba-closo-dodecaboranes and 1-(2-formylbenzyl)-1,2-dicarba-closo-dodecaborane have been obtained. The synthesized boron clusters could be of interest as promising building blocks in design of BNCT delivery agents.

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8.
Инвентарный номер: нет.
   
   C 10

   
    C-H functionalization of azines. Anodic dehydroaromatization of 9-(hetero)aryl-9,10-dihydroacridines [Electronic resource] / A. V. Shchepochkin, O. N. Chupakhin, V. N. Charushin, D. V. Steglenko, V. I. Minkin, G. L. Rusinov, A. I. Matern // RSC Advances. - 2016. - Vol. 6, № 81. - С. 77834-77840
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
HYDRIDE TRANSFER-REACTIONS -- AROMATIC-SUBSTITUTION -- NUCLEOPHILIC-SUBSTITUTION
Аннотация: Data on anodic dehydroaromatization of 9,10-dihydroacridines, bearing aryl and heteroaryl fragments, are presented. Effects of both electron-donating and electron-withdrawing substituents on the current-voltage characteristics of these compounds have been established. The experimental data proved to be in a good agreement with quantum chemical calculations. A simple and convenient method for the electrochemical conversion of dihydroacridines into the corresponding 9-(hetero)aryl-N-methylacridinium salts has been advanced

\\\\expert2\\NBO\\RSC Advances\\2016. Vol. 6, N 81. P. 77834.pdf
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9.
Инвентарный номер: нет.
   
   C 51

   
    Chemoenzymatic Synthesis and Antiherpes Activity of 5-Substituted 4,6-Difluorobenzimidazoles Ribo- and 2′-Deoxyribonucleosides [Электронный ресурс] / M. I. Kharitonova, I. V. Fateev, A. L. Kayushin, I. D. Konstantinova, S. K. Kotovskaya, V. L. Andropova, G. A. Galegov, V. N. Charushin, A. I. Miroshnikov // Synthesis (Germany). - 2016. - Vol. 48, № 3. - С. 394-406. - Bibliogr. : p. 405-406 (37 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
DRUG DISCOVERY- -- NUCLEOSIDES -- HERPES SIMPLEX VIRUS
Аннотация: A series of 5,6-disubstituted benzimidazole nucleosides, obtained earlier, did not show any significant antiviral activity at relatively low cytotoxicity in vitro. In the course of our research we have succeeded in introducing an additional fluorine atom into the benzimidazole ring system. A new series of 4,6-difluorobenzimidazoles, bearing various groups (fluoro-, methoxy-, ethoxy-, morpholino-, and pyrrolidino-) in the 5-position of the benzene ring, have been synthesized. All these compounds proved to be substrates for recombinant E. coli purine nucleoside phosphorylase (PNP) in the transglycosylation reaction. Effective methods for the synthesis of ribo- and 2′-deoxyribonucleosides with high yields (60–90%) have been described, and the formation of regioisomeric N3-nucleosides of benzimidazoles have been detected. The biological activity of the nucleosides obtained against herpes simplex virus type 1 (HSV-1) has been elucidated. All compounds show a low cytotoxicity in the cell culture Vero E6. 4,5,6-Trifluoro-1-(β-d-ribofuranosyl)benzimidazole and 5-methoxy-4,6-difluoro-1-(β-d-2′-deoxyribofuranosyl)benzimidazole proved to inhibit completely the progression of the virus cytopathic effect (CPE) at a multiplicity of infection (MOI) of 0.01 PFU/cell.

\\\\expert2\\nbo\\Synthesis\\2016, v. 48. p.394-406.pdf
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10.
Инвентарный номер: нет.
   
   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.)
ББК 54
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
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