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Volume 94, Nº 6 (2024)

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Articles

Synthesis, Reactions and Application of 2,2-Dimethyl-4-oxymethyl-1,3-dioxolane (A Review)

Nurieva E., Borisova Y., Raskildina G., Sultanova R., Zlotsky S.

Resumo

This review analyzes publications that present the results of studies of modern and traditional approaches to the synthesis of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane, as well as data on methods for its use in organic synthesis. The ways of obtaining enantiomerically pure 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolanes, necessary in the production of drugs, are shown. Publications devoted to the use of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane in pharmaceutical, medicinal chemistry and petrochemistry are presented.

Žurnal obŝej himii. 2024;94(6):664-690
pages 664-690 views

Diels–Alder Adducts of N-Substituted 2-Pyridones with Maleinimides. Synthesis and Antiviral Activity

Sorokina V., Kovalskaya A., Lobov A., Ilyina P., Zarubaev V., Tsypysheva I.

Resumo

Adducts of N-substituted 2-pyridones [pyridine-2(1H)-ones] and N-substituted maleic acid imides were synthesized under thermal conditions of the Diels–Alder reaction with yields from 68 to 97%. Cytotoxicity and antiviral activity of the obtained compounds were studied using a model of adenovirus infection [human adenovirus type 5 (AdV5)] in MA-104 cell culture. It was shown that the synthesized adducts have low toxicity and medium antiviral activity. Only 9-hexyl-2-phenyl-3a,4,7,7a-tetrahydro-1H-4,7-(epiminomethano)isoindole-1,3,8-trione has the most pronounced viral inhibitory properties with a selectivity index of 7.

Žurnal obŝej himii. 2024;94(6):691-698
pages 691-698 views

Synthesis and Structure of Ethyl 4-Aryl-2-oxo-2,3,4,10-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates

Podchezertseva K., Zamaraeva T., Slepova N., Dmitriev M.

Resumo

Ethyl 4-aryl-2-oxo-2,3,4,10-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates were prepared by three-component one-pot condensation of diethylmalonate, aromatic aldehyde, 2-aminobenzimidazole in ethanol in the presence of piperidine. The structure of the obtained compounds was determined by 1H, 13С NMR spectroscopy and single crystal X-ray diffraction analysis.

Žurnal obŝej himii. 2024;94(6):699-704
pages 699-704 views

Features of the Reaction of Ortho-Carboranyl Lithium with 3,6-Bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine

Moseev T., Smyshlyaeva L., Kopchuk D., Ishmetova R., Slepukhin P., Rybakova A., Rusinov G., Zyryanov G., Varaksin M., Charushin V., Chupakhin O.

Resumo

The action of in situ generated ortho-carboranyl lithium on 3,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetrazine leads to the formation of bis(ortho-carboranyl)diformylhydrazide as a product of the opening of the 1,2,4,5-tetrazine ring with the release of a nitrogen molecule, while the expected products of ipso-substitution of the pyrazole fragment were not detected. The structure of the obtained symmetrical bis(ortho-carboranyl)diformylhydrazide was established based on NMR spectroscopy, mass spectrometry and single crystal X-ray structural analysis.

Žurnal obŝej himii. 2024;94(6):705-711
pages 705-711 views

Derivatives of (–)-Cytisine with Thiourea Fragment. Synthesis and Antiviral Activity

Kovalskaya A., Lobov A., Zarubaev V., Tsypysheva I.

Resumo

New derivatives of the quinolizidine alkaloid, (–)-cytisine, with a substituted 2-pyridone ring and a thiourea moiety in the bispidin fragment of the molecule were synthesized. The ability of the synthesized cytisine-containing thioureas to inhibit the reproduction of human parainfluenza virus type 3 was assessed. It was found that the derivatives obtained by the reaction of benzoyl or phenyl isothiocyanate with (–)-cytisine, as well as its 9-bromo or 9,11-derivative, effectively suppress the reproduction of human parainfluenza virus type 3 (their selectivity indices are 56, 58 and 95, respectively), which confirms the promise of the chosen approach to synthetic modifications of the alkaloid (–)-cytisine in order to obtain effective antiviral agents on its basis.

Žurnal obŝej himii. 2024;94(6):712-721
pages 712-721 views

Synthesis of Betulonic and Betulinic Acids Derivatives with Sulfonamide Fragment Linked to the Triterpene Core by Amidoalkane Spaser

Komissarova N., Orlov A., Spirikhin L.

Resumo

A series of potentially biologically active sulfonamides of betulonic and betulinic acids with a sulfonamide fragment containing residues of dibutylamine or N-heterocycles, which is linked to a triterpene core by an amidoethane or amidopropane spacer, was synthesized. Betulonic acid sulfonamides were obtained by chlorohydride conjugation of acid with 2-aminoethane and 3-aminopropanesulfonamides and used as precursor compounds for the transition to similar betulinic acid derivatives by selective reduction of the 3-keto group with the action of NaBH4 in EtOH. The structure of all synthesized triterpene sulfonamides was confirmed by 1D and 2D NMR spectroscopy and mass spectrometry.

Žurnal obŝej himii. 2024;94(6):722-733
pages 722-733 views

Effect of Aminophenol and Amino Acids Derivatives on the Level of Nitrosyl Radical and Its Active Forms In Vitro

Ovsyannikova E., Burko A., Ksendzova G., Sorokin V., Karankevich E., Yurkova I.

Resumo

The effect of aminophenol, amino acids and their derivatives on the level of NO and its intermediates (NO2, N2O3) in an aqueous aerobic media (pH = 7.4) was studied using nitroprusside as a NO donor. It was found that the highest NOx scavenging activity is exhibited by 3-aminophenol (IC50 = 0.11 mM), 2-aminophenol (IC50 = 0.195 mM) and 4,6-di-tert-butyl-2-aminophenol (IC50 = 0.12 mM), standards: trolox (IC50 = 0.19 mM) and ascorbate (IC50 = 4.88 mM). Methylation of the OH group reduced the effectiveness of aminophenol. In the studied concentration range (0–70 mM), Tyr-Ala (IC50 = 5.0 mM) and β-Ala-His (IC50 = 35.0 mM) were more active than Phe-Ala (IC50 > 50 mM) and Gly-Gly (IC50 > 50 mM). Complexes Cu(Gly)2 and Cu(Gly-Gly)2 at low concentrations (0.05–0.5 mM) are 1.4–1.8 times more effective than Gly and Gly-Gly.

Žurnal obŝej himii. 2024;94(6):734-745
pages 734-745 views

Spectrophotometric Analysis of Copolyarylene Phthalides and Their Copolymers with Methyl Methacrylate and Styrene

Yumagulova R., Yangirov T., Ayupova A., Kraikin V.

Resumo

Sulfuric acid solutions of copolyarylene phthalides of the diphenyloxide series and their copolymers with methyl methacrylate and styrene were studied by the photometric method. According to spectral data, regardless of the ratio of single (α) and double (β + γ) phthalide groups in the macrochains of copolyarylene phthalides in their copolymers with methyl methacrylate, there are ~20–26 mol of MMA per 1 mol of phthalide units. The structure of copolyarylene phthalides is a determining factor in the formation of copolymers with styrene, in which either styrene units or phthalide fragments predominate (~15–40 and ~2–5 mol of styrene per mole of phthalide unit).

Žurnal obŝej himii. 2024;94(6):746-756
pages 746-756 views

Heteronuclear Glycinate Complexes of Fe(II), Fe(III) and Co(II), Their Model Parameters

Bobonazarzoda G.

Resumo

The system Fe(II)–Fe(III)–Co(II)–Gly–H2O was studied by the Clark–Nikolsky oxidation potential method at a temperature of 298.15 K, ionic strength of the solution [Na(H)CIO4] I = 1.0 mol/l. The formation of mononuclear and heteronuclear compounds of various compositions in the system was found: [FeHL(H2O)5]3+, [Fe(HL)2(H2O)4]3+, [Fe(HL)(OH)(H2O)4]2+, [СoL(H2O)5]+, [FeIIIСoIIL(H2O)11]4+, [FeIIIСoII(L)2(H2O)10]3+, [FeL(H2O)5]+, [Fe(HL)2(H2O)4]2+, [Fe(HL)(OH)(H2O)4]+ and [Fe(HL)(OH)2(H2O)3]0. The stability and model parameters of coordination compounds were calculated by the Yusupov oxidation function iteration method, and their coordination compound distribution diagrams were constructed. It was found that the heteronuclear complex [FeIIIСoIIL(H2O)11]4+ is the most stable, with an accumulation degree of 99.50%, and exists up to pH = 9.5.

Žurnal obŝej himii. 2024;94(6):757-765
pages 757-765 views

Influence of the Structure of Carbamoylmethylphosphine Oxides on the Extraction of Lanthanides(III) from Nitric Acid Solutions in the Presence of Dinonylnaphtalenesulfonic Acid

Turanov A., Karandashev V., Artyushin O., Sharova E.

Resumo

It was found that the extraction of lanthanides(III) from nitric acid solutions with solutions of carbamoylmethylphosphine oxides increases significantly in the presence of dinonylnaphthalene sulfonic acid. The stoichiometry of the extracted complexes was determined, and the influence of the composition of the aqueous phase, the nature of the organic solvent, and the structure of carbamoylmethylphosphine oxides on the efficiency of extraction of metal ions into the organic phase was considered.

Žurnal obŝej himii. 2024;94(6):766-774
pages 766-774 views

Thermal and Luminescent Properties of Multi-Ligand Complexes of Europium(III) with Pyrazine-2-carboxylic Acid

Kalinovskaya I., Zadorozhnaya A., Kuryavy V., Popov L.

Resumo

Eu(III) compounds with pyrazine-2-carboxylic acid and nitrogen- and phosphorus-containing neutral ligands were synthesized. Using the methods of chemical elemental and thermal analysis and IR spectroscopy, the composition of the complexes and the method of coordination of carboxylate ions were established. The most thermally stable compounds have been identified. The luminescent characteristics of complex compounds have been studied. It was found that the maximum luminescence intensity is characteristic of europium(III) pyrazinate with triphenylphosphine oxide. The morphological structure and dispersion of the complexes were determined.

Žurnal obŝej himii. 2024;94(6):775-784
pages 775-784 views