Russian Chemical Bulletin
type: channel
description: ISSN (print): 1066-5285, ISSN (online): 1573-9171 Editor-in-Chief: MIKHAIL P. EGOROV Publisher: Springer Indexed in: RUS White List (level 2), Scopus, Web of Science (SCIE)
language: en-US
publication name: Russian Chemical Bulletin
issn: 1066-5285
items: Computer-aided prediction of biological activity spectra for organic compounds: the possibilities and limitations
items: Crystal engineering as a scientific basis for modification of physicochemical properties of bioflavonoids
items: Nanostructured titanium dioxide for medicinal chemistry
items: Development of new antituberculosis drugs among of 1,3- and 1,4-diazines. Highlights and perspectives
items: TDDFT-modeling of theoretical UV spectra of binuclear sulfur-containing iron nitrosyl clusters and products of their decomposition
items: Nanohydroxyapatite and its textures as potential carriers of promising short-lived lead isotopes
items: Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine
items: Polymer particles containing Fe-based metalloporphyrin as a highly efficient stimulator of reactive oxygen species formation in vitro and in vivo
items: Synthesis, properties, and antibacterial activity of a new nitric oxide donor — a nitrosyl iron complex with 5-phenyl-1H-1,2,4-triazole-3-thiol
items: Enantioselective adsorption of dipeptides on chiral stationary phases with grafted macrocyclic antibiotics using glycylaspartic acid as an example
items: Modification of biologically active amides and amines with fluorine-containing heterocycles
items: Synthesis and antimicrobial activity of arabinogalactan-stabilized selenium nanoparticles from sodium bis(2-phenylethyl)diselenophosphinate
items: Transformations of A-seco-18αH-oleanane hydroxynitriles
items: Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes
items: Three-component green synthesis of 6-ethoxycarbonyl-5-methyl-7-(thien-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine, a promising antituberculosis drug
items: Iridoids from Phlomis ostrowskiana Regel plant
items: Novel 5-N,N-disubstituted-5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles: synthesis and study of neuroprotective and antiproliferative properties
items: Synthesis and antioxidant properties of (dodecylsulfanyl)methyl quercetin derivatives
items: Novel derivatives of 3,5-di-tert-butylpyrocatechol with pharmacophore substituents
items: Chemical constituents of the extracts of the knotwood of Pinus roxburghii Sarg. and their antioxidant activity
items: Xymedone conjugate with para-aminobenzoic acid. Estimation of hepatoprotective properties
items: Synthesis of glutaryl-containing derivatives of GRGD and KRGD peptides
items: Amperometric method for the determination of relative antioxidant activity of isobornylphenol
items: New ASGPR-targeted ligands based on glycoconjugated natural triterpenoids
items: Synthesis of daunorubicin conjugates with fragments of H type 5, Lea, Lex antigens and N-fucoglycan
items: Transport and toxicity of 5-fluorouracil, doxorubicin, and cyclophosphamide in in vitro placental barrier model based on BeWo b30 cells
items: Key structures for the synthesis of steroid antitumor agents. Synthesis of 16-dehydro-17-carbaldehydes of 13β- and 13α-estratriene series
items: Synthesis of 3β-methyl ether of dehydroepiandrosterone by biotransformation of 3β-methyl ether of cholesterol with cells of mycobacteria Mycobacterium sp.
items: Apoptotic effect of the anphen sodium antioxidant in combination with H2O2 on Lewis carcinoma cells
items: Potential of fluorescence polarization immunoassay for the detection of Aspergillus fumigatus galactomannan
items: New ditopic organic ligands with 2-pyridylbenzothiazole and 5-pyridylmethylidene-2-(methylthio)imidazolone fragments
items: Synthesis of new selenium-containing analogs of phenozan acid
items: Comparison of 2D and 3D cell cultures of colorectal adenocarcinoma as models for drug screening
items: Erratum to: Glycosylation in flow: effect of the flow rate and type of the mixer

Computer-aided prediction of biological activity spectra for organic compounds: the possibilities and limitations
type: item
description: We describe the current version of the PASS program for prediction of biological activity spectra of organic compounds based on analysis of structure—activity relationships (SAR) for a training set containing information on more than 1000 000 biologically active organic compounds. The average accuracy of prediction for more than 5 000 types of biological activity exceeds a value of 0.96. To analyze quantitative SAR, the GUSAR program was developed. The advantages of GUSAR were demonstrated in a number of computational experiments. The local versions of the PASS and GUSAR programs, as well as 19 freely available web services were developed. The latter are freely accessible via the Internet at http://way2drug.com/dr. The web services at the Way2Drug portal are used by more than 24 000 researchers working in about 100 countries. Currently, more than 830 000 predictions were made, the most promising compounds were selected for chemical synthesis, and priorities for testing their biological activity were established. The PharmaExpert software was developed to analyze the results of the PASS- and GUSAR-based predictions and to search for chemical compounds with necessary biological activity spectra. Combined use of the PASS, GUSAR, and PharmaExpert programs enables an assessment of the pharmacotherapeutic, adverse, and toxic effects of new compounds based on the systems pharmacology.
creator: V. V. Poroikov
creator: D. A. Filimonov
creator: T. A. Gloriozova
creator: A. A. Lagunin
creator: D. S. Druzhilovskiy
creator: A. V. Rudik
creator: L. A. Stolbov
creator: A. V. Dmitriev
creator: O. A. Tarasova
creator: S. M. Ivanov
creator: P. V. Pogodin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2143
ending page: 2154
doi: 10.1007/s11172-019-2683-0

Crystal engineering as a scientific basis for modification of physicochemical properties of bioflavonoids
type: item
description: Flavonoids are of interest for pharmacy and medicinal chemistry due to a wide range of biological activities. The major goal for the design of new drugs based on flavonoids is to increase bioavailability of pharmaceutical substances. Crystal engineering is a useful tool for this purpose. This review presents a systematic analysis of the publications on crystal engineering of flavonoids published between 2000 and 2019. The data on objects, methods of supramolecular synthesis, analysis, and preclinical studies of its products are summarized. The trends in crystal engineering of flavonoids are considered and promising areas for further research are identified. The review may be of interest for researchers engaged in the design of drugs with low bioavailability, including bioflavonoids.
creator: I. A. Selivanova
creator: R. P. Terekhov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2155
ending page: 2162
doi: 10.1007/s11172-019-2684-z

Nanostructured titanium dioxide for medicinal chemistry
type: item
description: The review considers methods for the synthesis of stoichiometric and nonstoichiometric nanostructured titanium dioxide for medicinal chemistry. The influence of the synthesis method on the amorphous atomic and crystal structures, specific surface area, morphology, and photooptical properties of the material is analyzed. The review compares the results of using stoichiometric and nonstoichiometric titanium dioxide in the synthesis of new organic molecules by cross-coupling of heteroarenes, which can be utilized in drugs.
creator: A. A. Rempel
creator: A. A. Valeeva
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2163
ending page: 2171
doi: 10.1007/s11172-019-2685-y

Development of new antituberculosis drugs among of 1,3- and 1,4-diazines. Highlights and perspectives
type: item
description: The properties of pyrimidine and pyrazine derivatives responsible for the existence of antituberculosis activity are considered. Examples of synthesis and biological activity of the most promising compounds containing the pyrimidine or pyrazine rings in the molecular structure are presented.
creator: E. V. Verbitskiy
creator: G. L. Rusinov
creator: V. N. Charushin
creator: O. N. Chupakhin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2172
ending page: 2189
doi: 10.1007/s11172-019-2686-x

TDDFT-modeling of theoretical UV spectra of binuclear sulfur-containing iron nitrosyl clusters and products of their decomposition
type: item
description: The UV spectra of four binuclear sulfur-containing iron nitrosyl clusters, namely, cationic Fe2{[S(CH2)2NH3]2(NO)4}SO4·2.5H20 and Fe2[(SC5H11NO2)2(NO)4]SO4·5H2O, anionic Na2[Fe2(S2O3)2(NO)4]·4H2O, and neutral [Fe2(SC5H6)2(NO)4], were modeled using time-dependent density functional theory (TDDFT) and compared with experimental results. It was determined that the strong bands at 310 and 360 nm in the experimental spectra correspond to electronic transitions (Fe—NO) → π*(Fe—NO), but the unshared electron pairs of sulfur atoms also contribute. The presence of an aromatic ring in the sulfur-containing ligand changes the form of the UV spectrum, as was observed in the experiment. Strong characteristic bands are absent from the theoretical spectra of possible products.
creator: N. S. Emel’yanova
creator: O. V. Pokidova
creator: N. A. Sanina
creator: S. M. Aldoshin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2190
ending page: 2196
doi: 10.1007/s11172-019-2687-9

Nanohydroxyapatite and its textures as potential carriers of promising short-lived lead isotopes
type: item
description: The possibility of sorption and cocrystallization binding of lead(n) with nanohydroxyapatite (HAP) acting as a potential carrier of short-lived lead radionuclides 211,212Pb was studied. The peculiarities of the kinetics were revealed, and the isotherms of sorption of lead ions on hydroxyapatite with different textures were constructed. A multistage sorption mechanism accompanied by a change in the structure and morphology of the sorbent was studied. The possibility of the formation of a new phase (hydroxypyromorphite) of lead during the sorption and cocrystallization interaction was shown. The introduction of lead into the synthesis of HAP at the early stages of crystallization exerts the highest effect on its morphology and structure. The optimization of the formation of the HAP-Pb composite over the course of the process will make it possible to use the short-lived 211Pb radionuclide in subsequent experiments.
creator: A. V. Severin
creator: M. A. Orlova
creator: E. S. Shalamova
creator: A. V. Egorov
creator: M. A. Sirotin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2197
ending page: 2204
doi: 10.1007/s11172-019-2688-8

Gold-catalyzed cyclization in the synthesis of antimitotic 2,3-dihydrobenzo[b]oxepine derivatives of colchicine
type: item
description: New allocolchicine derivatives bearing 2,3-dihydrobenzo[b]oxepine moiety were synthesized via gold-catalyzed cyclization as a key synthetic step. The obtained 2,3-dihydrobenzo[b]oxepine-containing allocolchicinoids possess cytotoxic activity against HEK293, PANC-1, COL0357, HeLa, and Colon26 cancer cell lines at low micromolar range of concentrations.
creator: S. Yu. Bukhvalova
creator: A. A. Maleev
creator: Yu. A. Gracheva
creator: Yu. V. Voitovich
creator: S. K. Ignatov
creator: E. V. Svirshchevskaya
creator: A. Yu. Fedorov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2205
ending page: 2215
doi: 10.1007/s11172-019-2689-7

Polymer particles containing Fe-based metalloporphyrin as a highly efficient stimulator of reactive oxygen species formation in vitro and in vivo
type: item
description: Reactive oxygen species are generated by the redox reaction involving metalloporphyrin and ascorbic acid (AA) and lead to oxidative stress followed by cancer cell death. Polymer particles based on the copolymer of lactic and glycolic acid (PLGA) containing FeIIICl-tetraphenylporphyrin (FeClTPP) were prepared and characterized. These particles in combination with AA exhibit cytotoxic activity against the K562 (human chronic myelogenous leukemia) and MCF7 (human breast adenocarcinoma) cell lines. Results in vitro indicated significant antitumor efficiency on mice inoculated with P388 leukemic cells and treated with FeClTPP/AA. The cytotoxic activity of the combined system is achieved due to the formation of reactive oxygen species. The application of this system to the study of anticancer efficiency in vivo on the model of mice that were hypodermically inoculated with P388 lymphocytic leukemia revealed a significant inhibition of tumor growth. The use of FeClTPP in combination with AA seems to be promising in cancer treatment.
creator: M. R. Faustova
creator: E. D. Nikolskaya
creator: M. D. Mollaev
creator: M. B. Sokol
creator: A. I. Zabolotsky
creator: O. A. Zhunina
creator: M. V. Fomicheva
creator: V. I. Schvets
creator: A. V. Lobanov
creator: N. G. Yabbarov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2216
ending page: 2224
doi: 10.1007/s11172-019-2690-1

Synthesis, properties, and antibacterial activity of a new nitric oxide donor — a nitrosyl iron complex with 5-phenyl-1H-1,2,4-triazole-3-thiol
type: item
description: A new binuclear μ-NSC-type nitrosyl iron complex [Fe2(SR)2(NO)4] (R is 5-phenyl-1H-1,2,4-triazole-3-thiolyl) was synthesized. The composition and structure of the newly synthesized complex were determined by atomic absorption, IR, EPR, and Mössbauer spectroscopy and SQUID magnetometry. Amperometric analysis showed that the new complex is an effective nitric oxide (NO) donor in a 1% aqueous DMSO solution. The amounts of NO generated by the complex [Fe2(SR)2(NO)4] in aqueous solutions at physiological pH values were determined. The new complex was shown to have higher antibacterial activity against the gram-positive bacteria Micrococcus luteus compared to kanamycin and streptomycin. According to assays, sulfur-containing ligands of the 1,2,4-triazole-3-thiol series are promising for the design of new antibacterial agents containing the {Fe(NO)2} structural moiety.
creator: N. A. Sanina
creator: V. A. Mumyatova
creator: A. A. Terent´ev
creator: R. B. Morgunov
creator: N. S. Ovanesyan
creator: A. V. Kulikov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2225
ending page: 2231
doi: 10.1007/s11172-019-2691-0

Enantioselective adsorption of dipeptides on chiral stationary phases with grafted macrocyclic antibiotics using glycylaspartic acid as an example
type: item
description: The chromatographic behavior and adsorption of enantiomers of glycylaspartic acid on the Nautilus-E chiral stationary phase with grafted eremomycin antibiotic were studied. Acetate buf er mixtures with variable pH prepared in a water—methanol mixed solvent (volume ratio 60 : 40) were used as acetate buf ers. The retention of Gly—Asp was found to be enantioselective and depending on the ratio of various ionic forms of dipeptide in the mobile phase. The ratio is determined by the pH. A model of adsorption equilibrium assuming independent binding of diverse ionic forms with the stationary phase, which is characteristic of energy uniformity, was proposed. This model is well consistent with the experimental data. Features of application of the equilibrium dispersion and transport dispersion dynamic elution models for the determination of the adsorption isotherms by the inverse method are discussed.
creator: L. D. Asnin
creator: A. N. Vasyanin
creator: M. V. Stepanova
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2232
ending page: 2240
doi: 10.1007/s11172-019-2692-z

Modification of biologically active amides and amines with fluorine-containing heterocycles
type: item
description: A synthetic approach to the modification of the drug “riluzole” with pharmacologically active fragments such as carbazole, tetrahydrocarbazole, phenothiazine, and aminothiophene, based on the copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition of azide-containing pharmacophores with “riluzole” decorated with 5-trifluoromethylhydantoin, has been suggested.
creator: V. B. Sokolov
creator: A. Yu. Aksinenko
creator: T. V. Goreva
creator: T. A. Epishina
creator: S. O. Bachurin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2241
ending page: 2244
doi: 10.1007/s11172-019-2693-y

Synthesis and antimicrobial activity of arabinogalactan-stabilized selenium nanoparticles from sodium bis(2-phenylethyl)diselenophosphinate
type: item
description: Water-soluble elemental selenium nanocomposites containing 0.8-3.9% Se were synthesized by oxidation of sodium bis(2-phenylethyl)diselenophosphinate in aqueous medium in the presence of the natural polysaccharide arabinogalactan as a stabilizer for nanoparticles. Using a complex of physicochemical research methods (TEM, XRD, IR spectroscopy), it was found that the nanocomposites were formed as spherical particles of amorphous selenium of 31–78 nm in size, which are dispersed in the polysaccharide matrix. For the nanocomposite containing 3.9% Se, a pronounced antimicrobial activity against the bacterial phytopathogen Clavibacter michiganensis subsp. sepedonicus was demonstrated.
creator: M. V. Lesnichaya
creator: S. F. Malysheva
creator: N. A. Belogorlova
creator: I. A. Graskova
creator: A. V. Gazizova
creator: A. I. Perfilyeva
creator: O. A. Nozhkina
creator: B. G. Sukhov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2245
ending page: 2251
doi: 10.1007/s11172-019-2694-x

Transformations of A-seco-18αH-oleanane hydroxynitriles
type: item
description: 2,3-Secooleanane hydroxynitriles undergo dehydration and anionotropic 1,2-migration of the methyl group C(24)H3 under the action of the SOCl2-CH2Cl2 system to form a mixture of isomeric Δ4-alkenes. A similar E1-elimination process in the presence of the H2SO4—AcOH system is accompanied by hydrolysis of the CN group giving A-ring unsaturated C(2)-ketones and diastereomeric ε-lactones. Epimeric 4,23-epoxides and isopropyl ketone were synthesized by oxidative transformations of 4,23-alkene, which was selectively formed from 2,3-secooleanane hydroxynitrile under the action of the POCl3-Py system. The in vitro cytotoxic evaluation by the MTT assay showed that the synthesized compounds are not toxic (IC50 > 100 μmol L−1) against the human cancer cell lines HEp-2, HCT116, MS, RD TE32, MCF-7, A549, and PC-3.
creator: A. V. Konysheva
creator: G. F. Krainova
creator: D. V. Eroshenko
creator: M. V. Dmitriev
creator: V. V. Grishko
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2252
ending page: 2261
doi: 10.1007/s11172-019-2695-9

Synthesis of 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed cyclization of indole-3-carbaldehyde oximes
type: item
description: A new method for synthesizing 11H-indolo[3,2-c]quinolines by SnCl4-catalyzed intramolecular electrophilic amination of 2-arylindole-3-carbaldehyde O-acetyl oximes was developed.
creator: N. A. Aksenov
creator: A. Z. Gasanova
creator: F. Yu. Prokonov
creator: D. A. Aksenov
creator: G. M. Abakarov
creator: A. V. Aksenov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2262
ending page: 2270
doi: 10.1007/s11172-019-2697-7

Three-component green synthesis of 6-ethoxycarbonyl-5-methyl-7-(thien-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine, a promising antituberculosis drug
type: item
description: A new simple, technological, and environmentally friendly method for the catalyst-free synthesis in water of a promising antituberculosis drug, 6-ethoxycarbonyl-5-methyl-7-(thien-2-yl)-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine, was developed. The amount of the solvent in the reaction mixture has a decisive effect on the yield and purity of the target product.
creator: Yu. A. Titova
creator: O. V. Fedorova
creator: G. L. Rusinov
creator: V. N. Charushin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2271
ending page: 2274
doi: 10.1007/s11172-019-2698-6

Iridoids from Phlomis ostrowskiana Regel plant
type: item
description: The structures of glycosylated iridoids extracted from Phlomis ostrowskiana R. plant species of Lamiaceae family were determined by mass spectrometry and NMR spectroscopy.
creator: D. A. Usmanov
creator: N. Sh. Ramazanov
creator: U. Yu. Yusupova
creator: D. V. Kurilov
creator: V. V. Kachala
creator: N. V. Krukovskaya
creator: N. G. Kolotyrkina
creator: I. V. Zavarzin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2275
ending page: 2278
doi: 10.1007/s11172-019-2699-5

Novel 5-N,N-disubstituted-5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles: synthesis and study of neuroprotective and antiproliferative properties
type: item
description: A series of eight novel 5-N,N-disubstituted-5-amino-3-(2-oxopropyl)-1,2,4-thiadiazoles with diverse lipophilic groups was obtained by reaction of 3-isothiocyanato-5-methylisoxazole with secondary amines. All the compounds of the series (independently on the type of the substituents) were found to be ineffective as inhibitors of calcium ions uptake in synaptosomes of rat cerebral cortex. Screening of the cytotoxicity to four cell lines (breast adenocarcinoma MCF-7, conditionnally normal breast epithelial cells MCF-10A, lung carcinoma A549, non-cancer lung fibroblasts VA13) revealed three compounds with good selectivity to cancer cells MCF-7 in comparison with non-cancer cell line MCF- 10A. These 1,2,4-thiadiazoles can serve as new leads for further study of their antitumor properties.
creator: A. N. Proshin
creator: T. P. Trofimova
creator: O. N. Zefirova
creator: L. N. Petrova
creator: D. A. Skvortsov
creator: S. O. Bachurin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2279
ending page: 2282
doi: 10.1007/s11172-019-2700-3

Synthesis and antioxidant properties of (dodecylsulfanyl)methyl quercetin derivatives
type: item
description: Mono-, bis-, and tris[(dodecylsulfanyl)methyl]-substituted quercetin derivatives were obtained by the reaction of quercetin with (N,N-diethylaminomethyl) dodecyl sulfide. These compounds under the conditions of AIBN-initiated oxidation of styrene (37 °C) terminated oxidation chains with a stoichiometric inhibition coefficients of 2.0±0.1 and rate constants of 5.1 · 105, 4.8 · 105, and 2.9 · 105 L mol-1 s-1, respectively. Based on the rate constants, the O-H bond energy values in the molecules of quercetin and its mono-, bis-, and tris- [(dodecylsulfanyl) methyl]-substituted derivatives were calculated and found to be equal to 334.4, 341.4, 341.7, and 344.7 kJ mol-1, respectively. It was established that the ability of the synthesized thio derivatives of quercetin to inhibit thermal autooxidation of lard (133 °C) is 1.3-2.7 times higher than that of the reference antioxidants (a-tocopherol, BHT, and BHA). According to the in silico assessment of acute toxicity for rats, the synthesized derivatives are low-toxic and non-toxic compounds.
creator: T. K. Bagavieva
creator: S. E. Yagunov
creator: S. V. Kholshin
creator: I. A. Emelyanova
creator: O. I. Prosenko
creator: A. E. Prosenko
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2283
ending page: 2289
doi: 10.1007/s11172-019-2701-2

Novel derivatives of 3,5-di-tert-butylpyrocatechol with pharmacophore substituents
type: item
description: New potentially bioactive derivatives comprising spatially hindered pyrocatechol linked to hydrazine, acid hydrazides (including isoniazid), and acetylcysteine by a covalent bridge, have been obtained. The structure of the obtained compounds was studied by X-ray diffraction analysis.
creator: L. Yu. Ukhin
creator: L. G. Kuz´mina
creator: D. V. Alexeenko
creator: L. V. Belousova
creator: A. S. Morkovnik
creator: E. N. Shepelenko
creator: V. A. Podshibyakin
creator: G. S. Borodkin
creator: O. I. Dmitrieva
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2290
ending page: 2297
doi: 10.1007/s11172-019-2702-1

Chemical constituents of the extracts of the knotwood of Pinus roxburghii Sarg. and their antioxidant activity
type: item
description: Chemical composition of the extract from the Pinus roxburghii Sarg. knotwood was studied for the first time. The extracts were obtained by ultrasound assisted sequential extraction of knotwood with hexane, acetone—water (95 : 5, v/v), and water. According to GC-MS analysis, hexane extract was dominated by monoterpenoids amounting to 53.57% and sesquiterpenoids (41.05%). Components of the acetone—water (95 : 5, v/v) extract were isolated, purified by HPLC, and identified by NMR spectroscopy and mass spectrometry as 2,3-bis(4-hydroxy-3-methoxybenzyl)butan-1,4-diol, 3-hydroxy-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one and 3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one. These compounds demonstrated notable antioxidant capacity determined using the amperometric method.
creator: D. E. Tsvetkov
creator: R. Kumar
creator: R. Devrani
creator: A. S. Dmitrenok
creator: Yu. E. Tsvetkov
creator: A. O. Chizhov
creator: A. Ya. Yashin
creator: Ya. I. Yashin
creator: V. K. Varshney
creator: N. E. Nifantiev
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2298
ending page: 2306
doi: 10.1007/s11172-019-2703-0

Xymedone conjugate with para-aminobenzoic acid. Estimation of hepatoprotective properties
type: item
description: A salt-like conjugate of xymedone with para-aminobenzoic acid in a series of pyrimidine derivatives was synthesized, and its hepatoprotective properties were studied. The compound studied exhibits a cytoprotective effect at a concentration of 25 μmol L-1 enhancing the viability of normal human hepatocyte cells of the Chang Liver line by 2.1 times against the background of the impact of the d-galactosamine toxicant, which was shown by experiments in vitro. The cytotoxicity of the compound (IC50) is 20.7 mmol L-1. The data indicating the hepatoprotective effect most pronounced at the early stages of therapy were obtained in experiments in vivo performed according to the therapeutic scheme on the model of CCl4-induced toxic hepatitis. The ability of the conjugate to exert reparative and protective effects was found, since the surface area of destructive-degenerative and necrotic injuries revealed in hematoxylin- and eosin-stained sections on the third day of intraperitoneal administration of the studied compound in a dose of 0.7 mg kg-1 decreased by 1.5 times. The areas of detection of lipid inclusions in frozen sections stained with Sudan black decreased by four times on the third day at a dose of 1.7 mg kg-1, whereas the decrease was 3.2 times on the seventh day at a dose of 0.7 mg kg-1 compared to the control group of animals administrated with saline. According to the biochemical parameters, positive effects on the secretory and synthetic functions of the liver, bilirubin metabolism, and metabolism of iron and magnesium were observed during the treatment of animals with the conjugate.
creator: A. A. Parfenov
creator: A. B. Vyshtakalyuk
creator: L. F. Gumarova
creator: L. R. Khasanshina
creator: G. P. Belyaev
creator: N. G. Nazarov
creator: D. A. Kondrashina
creator: I. V. Galyametdinova
creator: V. V. Zobov
creator: V. E. Semenov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2307
ending page: 2315
doi: 10.1007/s11172-019-2704-z

Synthesis of glutaryl-containing derivatives of GRGD and KRGD peptides
type: item
description: New derivatives of tetrapeptides GRGD (Gly-Arg(Pbf)-Gly-Asp(OMe)-OMe) and KRGD (Boc-Lys-Arg(Pbf)-Gly-Asp(OMe)-OMe) containing a glutaric acid fragment as a linker were synthesized. The linker provides the possibility for binding these derivatives to other biologically active molecules or nanoparticles.
creator: A. M. Demin
creator: A. V. Vakhrushev
creator: A. A. Tumashov
creator: V. P. Krasnov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2316
ending page: 2324
doi: 10.1007/s11172-019-2705-y

Amperometric method for the determination of relative antioxidant activity of isobornylphenol
type: item
description: The results on amperometric determination of antioxidant activity of a large group of iso-bornylphenols are present. The antioxidant activity is dependent on a degree of sterical hindering of hydroxy groups. The obtained data can be used for employing these antioxidants to decrease the oxidation of plastics, rubbers, and fuels.
creator: V. N. Belyaev
creator: O. V. Shchukina
creator: A. Ya. Yashin
creator: Ya. I. Yashin
creator: I. V. Fedorova
creator: I. Yu. Chukicheva
creator: A. V. Kutchin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2325
ending page: 2330
doi: 10.1007/s11172-019-2706-x

New ASGPR-targeted ligands based on glycoconjugated natural triterpenoids
type: item
description: New ligands for targeted delivery to the liver based on glycoconjugated natural triterpenoids are proposed. Simple chemical transformations of starting lupane triterpenes led to betulin or betulinic acid conjugates with N-acetyl-d-galactosamine linked through an isopropenyl fragment of the terpene skeleton. The obtained compounds were non-toxic in vitro to a series of cancer cell lines and normal cells. Molecular docking in silico and surface plasmon resonance spectroscopy revealed a high specificity of the synthesized glycotriterpenoids to the asialogly-coprotein receptor of hepatocytes.
creator: E. Yu. Yamansarov
creator: D. A. Skvortsov
creator: A. V. Lopukhov
creator: S. V. Kovalev
creator: S. A. Evteev
creator: R. A. Petrov
creator: N. L. Klyachko
creator: N. V. Zyk
creator: E. K. Beloglazkina
creator: Ya. A. Ivanenkov
creator: A. G. Majouga
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2331
ending page: 2338
doi: 10.1007/s11172-019-2707-9

Synthesis of daunorubicin conjugates with fragments of H type 5, Lea, Lex antigens and N-fucoglycan
type: item
description: Daunorubicin was conjugated with spacered N-glycosides of di- and trisaccharides containing terminal α-l-fucopyranose residues. The synthesis was carried out by N-monoalkylation of daunorubicin hydrochloride (1) in aqueous DMF in the presence of NaHCO3 using N-β-glycoside N-bromoacetylglycyl derivatives, namely, α-l-Fucp-(1→2)-β-d-Galp-(1→4)-β-d-Glcp-NHCOCH2NHCOCH2Br (2a), α-l-Fucp-(1→4)-[β-d-Galp-(1→3)]-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (3a), α-l-Fucp-(1→3)-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (4a), and α-l-Fucp-(1→6)-β-d-GlcpNAc-NHCOCH2NHCOCH2Br (5a). The conjugates of daunorubicin were obtained as hydrochlorides (2b-5b) in 40% yield. Their oligosaccharide components are fragments of H type 5, Lea, Lex antigens and N-fucolglycan, respectively. 0(I) Erythrocytes hemagglutination inhibition assay was performed with conjugates 2b–5b and Ulex europaeus (UEA 1), Lotus tetragonolobus (LTA), and Laburnum anagyroides (LAA) plant fucolectins.
creator: L. M. Likhosherstov
creator: O. S. Novikova
creator: N. G. Kolotyrkina
creator: V. E. Piskarev
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2339
ending page: 2343
doi: 10.1007/s11172-019-2708-8

Transport and toxicity of 5-fluorouracil, doxorubicin, and cyclophosphamide in in vitro placental barrier model based on BeWo b30 cells
type: item
description: An in vitro placental barrier model based on human choriocarcinoma BeWo b30 cell line was considered as a method of preclinical study of the transport and toxicity of antitumor agents and other organic compounds. Low permeabilities were found for 5-fluorouracil as an example of hydrophilic compound and for doxorubicin as an example of a lipophilic compound with a high degree of binding to proteins and DNA and a high permeability was found for cyclophosphamide as an example of lipophilic compound with a low degree of binding to proteins. Using impedance spectrometry and cell viability assessment via reduction of resazurin to resorufin, a pronounced cytotoxic effect of doxorubicin and good tolerance of 5-fluorouracil and cyclophosphamide by the cells were shown for drug concentrations equal to the maximum concentrations in the patients’ blood during the treatment of breast cancer.
creator: E. N. Knyazev
creator: S. V. Nikulin
creator: A. Yu. Khristichenko
creator: T. N. Gerasimenko
creator: O. V. Kindeeva
creator: V. A. Petrov
creator: G. A. Belyakova
creator: D. V. Maltseva
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2344
ending page: 2349
doi: 10.1007/s11172-019-2709-7

Key structures for the synthesis of steroid antitumor agents. Synthesis of 16-dehydro-17-carbaldehydes of 13β- and 13α-estratriene series
type: item
description: A convenient preparative synthesis of 3-methoxyestra-1,3,5(10),16-tetraene-17-carb-aldehyde and its epimeric 13α-analog, the key structures in the synthesis of steroid estrogen receptor modulators and potential antitumor agents, was developed starting from estrone and including the generation of intermediate 16-dehydro-17-carbonitriles and their reaction with diisobutylaluminum hydride. The influence of conformational dif erences in the steroid molecules with the natural 13β- and epimeric 13α-configurations on the reactivity of intermediate compounds and the stereoselectivity of the trimethylsilyl cyanide addition to the carbonyl group of methyl ethers of epimeric estrones was considered.
creator: M. O. Tserfas
creator: Yu. V. Kuznetsov
creator: I. S. Levina
creator: I. V. Zavarzin
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2350
ending page: 2354
doi: 10.1007/s11172-019-2710-1

Synthesis of 3β-methyl ether of dehydroepiandrosterone by biotransformation of 3β-methyl ether of cholesterol with cells of mycobacteria Mycobacterium sp.
type: item
description: 3p-Methyl ether of dehydroepiandrosterone was obtained by microbiological transformation of 3ß-methyl ether of cholesterol with Mycobacterium sp. Androstane-3,17-dione, androst-4-ene-3,17-dione, and androsta-1,4-diene-3,17-dione were minor transformation products.
creator: V. A. Andryushina
creator: T. S. Stytsenko
creator: N. V. Karpova
creator: V. V. Yaderets
creator: I. V. Zavarzin
creator: D. V. Kurilov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2355
ending page: 2358
doi: 10.1007/s11172-019-2711-0

Apoptotic effect of the anphen sodium antioxidant in combination with H2O2 on Lewis carcinoma cells
type: item
description: It was shown by immunoblotting that the introduction of an antitumor antioxidant, sodium 2-carboxy-2-(N-acetylamino)-3-(3,5-di-tert-butyl-4-hydrophenyl)propanoate (anphen sodium), into a suspension of Lewis carcinoma cells induces a sharp decrease in the contents of the monomer and homodimer of the anti-apoptotic Bcl-2 protein. According to fluorescence analysis, the number of apoptotic cells sharply increased 1 h after exposure to anphen sodium; preliminary addition of 5 μmol L-1 of hydrogen peroxide increased the cell membrane permeability of anphen sodium and the number of apoptotic cells. The onset of apoptosis detected using fluorophores is comparable in time with the start of the decline of the Bcl-2 level. It was assumed that the mechanism of action of anphen sodium may include the interaction of the agent with the hydrophobic (BH3) domain of Bcl-2 family proteins.
creator: E. M. Mil’
creator: V. N. Erokhin
creator: V. I. Binyukov
creator: A. A. Albantova
creator: A. A. Volod’kin
creator: A. N. Goloshchapov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2359
ending page: 2364
doi: 10.1007/s11172-019-2712-z

Potential of fluorescence polarization immunoassay for the detection of Aspergillus fumigatus galactomannan
type: item
description: Galactomannan (GM) is a specific polysaccharide antigen of opportunistic mold fungi of the genus Aspergillus. The detection of GM in patients’ biological fluids is a reliable criterion for the diagnosis of invasive pulmonary aspergillosis, a severe disease. In this report, we evaluated the analytical capabilities of the fluorescence polarization immunoassay (FPIA) for detection of GM. Using FPIA, the high affinity of the monoclonal antibody 7B8 to the synthetic oligosaccharide β-d-Galf-[(1→5)-β-d-Galf]3-(1→6)-α-d-Manp related to the galactomannan fragment was shown. The binding constant in this interaction was found to be equal to (1.02±0.01) • 108 L mol-1. The detection limit determined for this oligosaccharide with the competitive FPIA method is 3 ng mL-1. The data obtained indicate the possibility of using FPIA for the diagnosis of invasive aspergillosis.
creator: V. B. Krylov
creator: M. I. Petruk
creator: M. P. Karimova
creator: L. I. Mukhametova
creator: A. L. Matveev
creator: N. V. Tikunova
creator: S. A. Eremin
creator: N. E. Nifantiev
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2365
ending page: 2369
doi: 10.1007/s11172-019-2713-y

New ditopic organic ligands with 2-pyridylbenzothiazole and 5-pyridylmethylidene-2-(methylthio)imidazolone fragments
type: item
description: New ditopic organic ligands with (pyridylmethylidene)imidazolone and pyridylbenzothi-azole moieties were synthesized by Cu-catalyzed azide-alkyne cycloaddition of 6-(prop-2-yn-1yloxy)-2-(pyridin-2-yl)benzothiazoleto3-azidoalkyl-5-[(Z-(pyridin-2-yl)methylidene]-2-(methylthio)dihydro-4H-imidazol-4-ones. The synthesized ligands (L) react with copper(ii) chloride to give coordination compounds of general formula LCuCl2 with coordination of the copper ion on the pyridylbenzothiazole fragment.
creator: E. S. Barskaya
creator: N. M. Madatli
creator: M. S. Abramovich
creator: N. V. Zyk
creator: A. G. Majouga
creator: A. V. Berezina
creator: E. K. Beloglazkina
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2370
ending page: 2373
doi: 10.1007/s11172-019-2714-x

Synthesis of new selenium-containing analogs of phenozan acid
type: item
description: Selenium-containing analogs of phenozan acid, [3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propylseleno]ethanoic and 3-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propylseleno]propanoic acids, were synthesized from bis-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]diselenide. The possibility of functionalization of the obtained compounds via the esterification and preparation of potassium salts was demonstrated. According to the in silico evaluation of acute toxicity towards rats, the synthesized compounds are low toxic and non-toxic substances.
creator: S. V. Kholshin
creator: S. E. Yagunov
creator: N. V. Kandalintseva
creator: A. E. Prosenko
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2374
ending page: 2376
doi: 10.1007/s11172-019-2715-9

Comparison of 2D and 3D cell cultures of colorectal adenocarcinoma as models for drug screening
type: item
description: The cytostatic effects of 5-fluorouracil, oxaliplatin, and 4-(5-methyl-5H-[1,3]dioxolo[4,5-f]-indol-7-yl)-3-(5-fluoro-1-benzofuran-3-yl)-1 H-pyrrole-2,5-dione (9-ING-41), a new glycogen synthase kinase-3 inhibitor, were evaluated in 2D and 3D models of HT-29 colorectal adenocarcinoma cells. The HT-29 cells cultured in 3D were resistant to the test drugs, while in the case of the 2D model, not only cytostatic but also cytotoxic effect was observed. The highest cytotoxic effect was detected upon the addition of 9-ING-41, at high concentrations of which the cell viability decreased to 50% after 3 h of incubation. The results indicate that 3D cultures reproduce the tumor structure and drug resistance more accurately.
creator: A. A. Poloznikov
creator: S. V. Nikulin
creator: L. V. Bolotina
creator: I. N. Gaisina
creator: B. Ya. Alexeev
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2377
ending page: 2380
doi: 10.1007/s11172-019-2716-8

Erratum to: Glycosylation in flow: effect of the flow rate and type of the mixer
type: item
description: To the article “Glycosylation in flow: effect of the flow rate and type of the mixer,” by I. V. Myachin, A. V. Orlova, and L. O. Kononov, Vol. 68, No. 11, pp. 2126–2129, November, 2019. In the original international version of the article, one phrase was omitted. To be added: This work was financially supported by the Russian Science Foundation (Project No. 16-13-10244-P).
creator: I. V. Myachin
creator: A. V. Orlova
creator: L. O. Kononov
rights: Copyright (c) 2019 Springer Science+Business Media, LLC, part of Springer Nature
date: 2019-12-01
publication date: 2019-12-01
volume: 68
number: 12
starting page: 2416
ending page: 2416
doi: 10.1007/s11172-019-2717-7