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1.
Инвентарный номер: нет.
   

   
    Synthesis of pyrimidine conjugates with 4-(6-amino-hexanoyl)-7,8-difluoro-3,4-dihydro-3-methyl-2h-[1,4] benzoxazine and evaluation of their antiviral activity / V. P. Krasnov, V. V. Musiyak, G. L. Levit [et al.] // Molecules. - 2022. - Vol. 27, № 13. - Ст. 4236
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
PYRIMIDINE
Аннотация: A series of pyrimidine conjugates containing a fragment of racemic 7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its (S)-enantiomer attached via a 6-aminohexanoyl fragment were synthesized by the reaction of nucleophilic substitution of chlorine in various chloropyrimidines. The structures of the synthesized compounds were confirmed by 1H, 19F, and 13C NMR spectral data. Enantiomeric purity of optically active derivatives was confirmed by chiral HPLC. Antiviral evaluation of the synthesized compounds has shown that the replacement of purine with a pyrimidine fragment leads to a decrease in the anti-herpesvirus activity compared to the lead compound, purine conjugate. The studied compounds did not exhibit significant activity against influenza A (H1N1) virus.

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2.
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    Oximes of fluoroalkyl-containing 1,3-diketones: specific features of synthesis, analysis, and thermal stability / N. S. Boltacheva, P. A. Slepukhin, M. G. Pervova [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 4. - P1464-1473
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Nitrosation of lithium 1,3-diketonates bearing fluoroalkyl and aryl (or hetaryl) substituents in positions 1 and 3 results in 3-polyfluoroalkyl-1,2,3-propanetrione 2-oximes (from this point on, oximes). Under similar conditions, lithium (Z)-1,1,1-trifluoro-4-oxo-4-(thien-2-yl)-2-buten-2-olate forms a hydration product of the corresponding oxime. Nitrosation of fluoroalkyl-containing lithium 1,3-diketonates is accompanied by retro-decomposition of the initial lithium 1,3-diketonates and the target oximes (or their hydration products) followed by oxidation and hydrolysis of the reaction products. Under the GC-MS conditions, the oximes undergo partial thermal decomposition to 2-aryl(hetaryl)-2-oxoethanenitriles. An analysis of solutions of the oximes in DMSO-d6 by 1H and 19F NMR spectroscopies revealed isomerization and hydration of these compounds. The temperature ranges of stability of the oximes were determined by thermogravimetric analysis and differential thermal analysis. The molecular and crystal structures of 4,4-difluoro-1-(4-methoxyphenyl)-1,2,3-butanetrione 2-oxime and 4,4,4-trifluoro-1-(thien-2-yl)-1,2,3-butanetrione 2-oxime were determined by X-ray diffraction.

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3.
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    Oximes of fluoroalkyl-containing 1,3-diketones: specific features of synthesis, analysis, and thermal stability / N. S. Boltacheva, P. A. Slepukhin, M. G. Pervova [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 7. - P1464-1473
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Nitrosation of lithium 1,3-diketonates bearing fluoroalkyl and aryl (or hetaryl) substituents in positions 1 and 3 results in 3-polyfluoroalkyl-1,2,3-propanetrione 2-oximes (from this point on, oximes). Under similar conditions, lithium (Z)-1,1,1-trifluoro-4-oxo-4-(thien-2-yl)-2-buten-2-olate forms a hydration product of the corresponding oxime. Nitrosation of fluoroalkyl-containing lithium 1,3-diketonates is accompanied by retro-decomposition of the initial lithium 1,3-diketonates and the target oximes (or their hydration products) followed by oxidation and hydrolysis of the reaction products. Under the GC-MS conditions, the oximes undergo partial thermal decomposition to 2-aryl(hetaryl)-2-oxoethanenitriles. An analysis of solutions of the oximes in DMSO-d6 by 1H and 19F NMR spectroscopies revealed isomerization and hydration of these compounds. The temperature ranges of stability of the oximes were determined by thermogravimetric analysis and differential thermal analysis. The molecular and crystal structures of 4,4-difluoro-1-(4-methoxyphenyl)-1,2,3-butanetrione 2-oxime and 4,4,4-trifluoro-1-(thien-2-yl)-1,2,3-butanetrione 2-oxime were determined by X-ray diffraction.

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4.
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    15N chemical shifts and Jnn-couplings as diagnostic tools for determination of the azide-tetrazole equilibrium in tetrazoloazines / S. L. Deev, T. S. Shestakova, Z. O. Shenkarev [et al.] // Journal of Organic Chemistry. - 2022. - Vol. 87, № 1. - P211–222
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Selectively 15N-labeled tetrazolo[1,5-b][1,2,4]triazines and tetrazolo[1,5-a]pyrimidines bearing one, two, or three 15N labels were synthesized. The synthesized compounds were studied by 1H, 13C, and 15N NMR spectroscopy in DMSO and TFA solutions, where the azide–tetrazole equilibrium can lead to the formation of two tetrazole (T, T′) isomers and one azide (A) isomer for each compound. Incorporation of the 15N-label(s) leads to the appearance of 15N–15N coupling constants (JNN), which can be easily measured via simple 1D 15N NMR spectra, even at natural abundance between labeled and unlabeled 15N atoms. The chemical shifts for the 15N nuclei in the azole moiety are very sensitive to the ring opening and azide formation, thus providing information about the azido–tetrazole equilibrium. At the same time, the 1–2JNN couplings between 15N-labeled atoms in the azole and azine fragments unambiguously determine the fusion type between tetrazole and azine rings in the cyclic isomers T and T′. Thus, combined analysis of 15N chemical shifts and JNN values in selectively isotope-enriched compounds provides an effective diagnostic tool for direct structural determination of tetrazole isomers and azide form in solution. This method was found to be the most simple and efficient way to study the azido–tetrazole equilibrium.

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5.
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    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 / T. D. Moseev, I. A. Lavrinchenko, M. V. Varaksin [et al.] // RSC Advances. - 2021. - Vol. 11, № 11. - P6407-6414
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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6.
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    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.

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7.
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    Betaine–N-heterocyclic carbene interconversions of quinazolin-4-one imidazolium mesomeric betaines. sulfur, selenium, and borane adduct formation / S. L. Deev, E. Sheina, T. S. Shestakova [и др.] // European journal of organic chemistry. - 2020. - № 4. - С. 450-465
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
ANIONIC NHCS -- BETAINES -- BORON COMPOUNDS -- CARBENES -- CYCLIC BORATES -- IMIDAZOL-2-YLIDENE
Аннотация: Reaction of N-alkylated imidazoles with 2-chloro-4-quinazolinone gave mesomeric betaines, 2-(1-alkyl-1H-imidazolium-3-yl)quinazolin-4-olates, for which three tautomeric forms of N-heterocyclic carbenes (NHCs) can be formulated, in addition to an anionic NHC after deprotonation. The NHC tautomers were trapped with sulfur, selenium, triethylborane, and triphenylborane as thiones, selenones and borane adducts, respectively. We obtained two isomers of the cyclic borane adducts, diazaboroloquinazolinones with [1,5-a] and [5,1-b]-type fusion between the quinazolinone and the diazaborole rings. They correspond to two different NHC tautomers and to the anionic NHC derived thereof. The third NHC tautomer was trapped as a non-cyclic adduct with tris(pentafluorophenyl)borane by coordination to the quinazoline oxygen atom. 2D 1H-15N HMBC experiments of 15N-labeled quinazolinone fragments, quantitative measurements of long-range 1H-15N coupling constants (JHN), and five X-ray single crystal analyses have been carried out for the structure elucidations and to gain insight into the NMR spectroscopic properties of these compounds.

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8.
Инвентарный номер: нет.
   
   E 43

   
    Electrophilic heterocyclization reactions of allylamino- and propargylamino-substituted sym-tetrazines in the presence of HgI2 / R. I. Ishmetova, I. A. Belyaninova, N. K. Ignatenko, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2017. - Vol. 53, № 2. - P213-218
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
1,2,4,5-TETRAZINES -- ELECTROPHILIC HETEROCYCLIZATION -- IMIDAZO[1,2-B][1, 2, 4, 5]TETRAZINES -- MERCURY(ii) IODIDE -- NUCLEOPHILIC SUBSTITUTION
Аннотация: A range of 3-azolyl-6-methylimidazo[1,2-b][1,2,4,5]tetrazines was obtained for the first time by electrophilic heterocyclization of 6-allylamino-3-azolyl- and 3-azolyl-6-propargylamino-1,2,4,5-tetrazines in the presence of HgI2. The structures of the starting materials and final products were confirmed by 1Н and 13С NMR spectroscopy, elemental analysis, and X-ray structural analysis.

\\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2017 v.53 p.213-218.pdf
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9.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis, structure and photoluminescent properties of BF2 and BPh2 complexes with N,O-benzazine ligands [Electronic resource] / E. V. Nosova, T. N. Moshkina, G. N. Lipunova, I. V. Baklanova , P. A. Slepukhin, V. N. Charushin // Journal of Fluorine Chemistry. - 2015. - Vol. 175. - С. 145-151. - Bibliogr. : p. 150-151 (29 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
N,O-BIDENTATE LIGANDS -- BPh2 COMPLEXES -- BF2 COMPLEXES
Аннотация: Novel N,O-bidentate BF2 and BPh2 complexes have been prepared in good to excellent yields through coordination of 8-hydroxy-2-methylquinolines and 2-(2-hydroxyphenyl)-3H-quinazolin-4-ones with boron trifluoride etherate or triphenylborane under mild conditions. All complexes have been characterized by H-1, B-11 and F-19 NMR, mass-spectrometry and X-ray crystallography data. Some complexes have been found to exhibit a significant fluore.scence in acetonitrile solutions. Electronic and site effects of substituents in both heterocyclic and phenol fragments proved to have a profound impact on quantum yields.

\\\\expert2\\nbo\\Journal of Fluorine Chemistry\\2015,V.175, p.145-151.pdf
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10.
Инвентарный номер: нет.
   
   S 98

   
    Synthesis, photochemical and luminescent properties of (E)-2-(2-hydroxyarylethylene)-3-phenylquinazolin-4(3H)-ones [Electronic resource] / I. G. Ovchinnikova, G. A. Kim, E. G. Matochkina, M. I. Kodess, N. V. Barykin, O. S. Eltsov, E. V. Nosova, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2015. - Vol. 63, № 11. - С. 2467-2477. - Bibliogr. : p. 2477 (22 ref.)
ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
(E)-2-STYRYLQUINAZOLIN-4(3H)-ONES -- LUMINESCENCE -- ORTHO-HYDROXYSTYRYLQUINAZOLINONES
Аннотация: Photoinduced transformations of 2-styrylquinazolinones in solutions were studied using absorption and NMR spectroscopy methods. A possibility of control of the photochemical isomerization rate of quinazolinone 2-(hydroxyaryl)ethenyl derivatives by changing the pH of the medium was demonstrated. The bases and the solvent nature also affect the luminescence intensity of solutions of these compounds in the wavelength range of 550-650 nm. The differences in the steric organization of the ortho-hydroxystyryldiazinone system in crystals and in solutions related to the turn of the aryl group were found. Their influence on the competing processes of luminescence and photochemical transformation of the ethylene fragment were shown. The fact of reversible photo/thermal E-Z-isomerization was established for (E)-2-(2-hydroxystyryl)-3-phenylquinazolin-4(3H)-one.

\\\\expert2\\nbo\\Russian Chemical Bulletin\\2015, 63 (11), 2467-2477.pdf
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