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Vol 93, No 4 (2023)
Articles
Synthesis, anticholinesterase and anti-radical activity of 2,3,5-trisubstituted 4H-imidazol-4-ones, green fluorescent protein chromophore analogues
Abstract
The one-pot synthesis of N -substituted α,β-dehydrotyrosyl dipeptides was carried out by the azlactone method. The target dipeptides were obtained in good yields (53-79%). From the latter, 2,3,5-trisubstituted 4-imidazolones were obtained using 1,1,1,3,3,3-hexamethyldisilazane as a dehydrating agent. It was found that in the case of β-alanine-containing peptides, abstraction of the methyl ester of acrylic acid and the formation of 2,5-disubstituted 4-imidazoline were observed. Antiradical and anticholinesterase properties of the synthesized compounds were studied. Docking analysis was carried out for both some dipeptides and imidazole-4-ones.
Žurnal obŝej himii. 2023;93(4):495-506
495-506
Synthesis of tetrazinyl biradicals containing a p-phenylene fragment
Abstract
3,3′-(1,4-Phenylene)bis[1-(4-R-phenyl)-5-phenyl-5,6-dihydro-1,2,4,5-tetrazinium] perchlorates were transformed into stable tetrazinyl biradicals by the action of D-glucose in slightly alkaline medium (NH4OH) in the presence of air oxygen. The tetrazinyl biradicals were isolated in individual state and characterized by cyclic voltammetry, elemental analysis, IR, UV, EPR spectroscopy methods.
Žurnal obŝej himii. 2023;93(4):507-515
507-515
Synthesis of diethyl 6-amino-1,4-diaryl-2-oxo1,2,3,4-tetrahydropyridin-3,5-dicarboxylates based on the reaction of arylmethylidenecyanoacetic esters with N-arylamido esters of malonic acid
Abstract
The reaction of arylmethylidenecyanoacetic esters with N -arylamides of malonic acid led to the formation of previously unknown diethyl 6-amino-1,4-diaryl-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxylates in 15-83% yields. Antibacterial activity of some obtained compounds was studied.
Žurnal obŝej himii. 2023;93(4):516-524
516-524
Synthesis and effect of substituted pyrido[2,3-d]pyrimidine-2,4-diones on In Vitro tumor dna methylation
Abstract
Reaction of 3-diethylamino-1-aryl-, 3-diethylamino-1-aryl-2-phenyl(4-halophenyl)propane-1-ones hydrochlorides with 6-amino-1,3-dimethyluracil results in heterocyclization products, namely 1,3-dimethyl-7-aryl-5,6dihydro-1 H -pyrido[2,3- d ]pyrimidine-2,4-diones, 1,3-dimethyl-7-aryl-6-phenyl(4-halophenyl)-5,6-dihydro1 H -pyrido[2,3- d ]pyrimidine-2,4-diones and 1,3-dimethyl-7-aryl-6-phenyl-(4-halophenyl)-1 H -pyrido[2,3- d ] pyrimidine-2,4-diones. The effect of the synthesized compounds in vitro tumor DNA methylation was studied.
Žurnal obŝej himii. 2023;93(4):525-530
525-530
Selective oxidation of the 4-ethyl-3-methylcinnoline methylene group by al2o3-supported chromium oxide
Abstract
The optimal conditions for the oxidation of the methylene group in 4-ethyl-3-methylcinnoline to the corresponding ketone, 3-methyl-4-acetylcinnoline, were selected. It was shown that preliminary deposition of 4-ethyl-3-methylcinnoline on some inorganic substrates has a significant effect both on the selectivity of the oxidation of only the methylene group and on a high degree of conversion to the target product.
Žurnal obŝej himii. 2023;93(4):531-538
531-538
Mass-spectrometric study of substituted (β-hydroxy-, β-acetoxy)sulfides and -sulfones of 1,3-dioxepane series using electron ionization
Abstract
The electron ionization mass spectra of substituted (β-hydroxy)sulfides, -sulfones, and their corresponding acetates of the 1,3-dioxepane series were studied. The main regularities in the pathways of fragmentation of their molecular ions were revealed. It was shown that during electron ionization, the main directions of decomposition of the studied compounds are due to the elimination of substituents in the 1,3-dioxepane ring. For 6-phenylthio-1,3-dioxepanes and 6-phenylsulfonyl-1,3-dioxepanes, the formation of ions associated with the breaking of C-S bonds with charge localization on the sulfur-containing fragment is observed.
Žurnal obŝej himii. 2023;93(4):539-547
539-547
Hydrogermylation of allylsilanes and -germanes
Abstract
The reactions of hydrogermylation of allylsilanes and -germanes R3MAll (M = Si, Ge; R = Cl, EtO, Me) by hydridgermanes R3GeH (R = Cl, Me) and trichlorogermane ether 2Et2O·HGeCl3 were studied. It has been established that small amounts of mono- (β- and γ-adducts) and double germylation products and, mainly, polymers are formed in reactions with ether. During hydrogermylation of Me3SiAll with trichlorogermane, insignificant amounts of β-adduct were recorded, but mainly in the entire series of experiments with Cl3GeH, γ-adducts are formed. In the catalytic reactions of allylsilanes and -germanes with trimethylgermane, exclusively γ-adducts are formed regardless of the framing of silicon and germanium atoms. A scheme of the possible course of the studied reactions is proposed. The identification of synthesized compounds was carried out using the methods of gas-liquid chromatography, 1Н, 13С NMR spectroscopy and chromatography-mass spectrometry
Žurnal obŝej himii. 2023;93(4):548-560
548-560
Synthesis of ethyl 2-methyl-4-(diethoxyphosphoryl)4,7-dihydro-5H-thiopyrano[3,4-b]furan-5-carboxylate and its functionalization at the position 3
Abstract
Ethyl 2-methyl-4-(diethoxyphosphoryl)-4,7-dihydro-5 Н -thiopyrano[3,4- b ]furan-5-carboxylate was synthesized. It was shown that at elevated temperatures it is acetylated in presence of tin tetrachloride and chloromethylated with paraformaldehyde-hydrogen chloride system in the presence of zinc dichloride at the positon 3 of heterocyclic system. Reaction of chloromethyl derivative with N -, S - and О -nucleophiles were studied.
Žurnal obŝej himii. 2023;93(4):561-576
561-576
Synthesis and extraction properties of 4,5-diphosphorylated triazoles
Abstract
A method for the synthesis of 4,5-diphosphorylated 1,2,3-triazoles has been developed, and the extraction of U(VI), Th(IV), and lanthanides(III) from nitric acid solutions by them was studied. A synergistic effect was found in the extraction of metal ions with mixtures of 4,5-diphosphorylated 1,2,3-triazoles and dinonylnaphthalenesulfonic acid. The stoichiometry of the extracted complexes was determined, and the influence of the structure of the extractant and the concentration of HNO3 in the aqueous phase on the efficiency of the extraction of metal ions into the organic phase was considered. It was established that 4,5-diphosphorylated 1,2,3-triazole with the octyl substituent at nitrogen atom has the highest extraction ability with respect to actinides and lanthanides in nitric acid media.
Žurnal obŝej himii. 2023;93(4):577-585
577-585
Spectrophotometric study of basic properties of glycosylated tetraphenylporphin derivatives
Abstract
The paper presents the results of spectrophotometric study of the basic properties of glycosylated substituted derivatives of 5,10,15,20-tetraphenylporphyrin, namely 5-(4′- O -galactosylphenyl)-10,15,20-tris( N -methylpyridin-3-yl)porphine, 5,15-bis(4′- O -galactosylphenyl)-10,20-bis( N -methylpyridin-3-yl)porphine, 5,10,15,20-tetra( N -methylpyridin-3-yl)porphin, 5,10,15,20-tetra(4- O -galactosylphenyl)porphin. The basic properties of the studied ligands in acetonitrile at 298 K were studied by spectrophotometric method. The effect of glycosylated fragments, as constituents of a macromolecule, on protolytic equilibria during acid-base interactions of the ligand in basic media and the change in the reactivity of porphyrin ligands depending on the nature of the peripheral substituent was analyzed.
Žurnal obŝej himii. 2023;93(4):586-592
586-592
Preparation, thermal properties and electrical conductivity of solutions of pyridinium ionic liquids with tetrachloroferrate anion
Abstract
Thermal stability of N -alkylpyridinium tetrachloroferrates(III) [C5H5NR]FeCl4 [R = C4H9, (CH2)3CN, CH2C6H5, C8H17, C10H21] in air in the range of 25-600°C was studied, as well as the thermal stability of N -alkylpyridinium chlorides. The equivalent electrical conductivity of N -alkylpyridinium tetrachloroferrates(III) in acetonitrile solution at 25°C was investigated. The ionic association constants K a , the limiting molar electrical conductivity (λ0) and the standard Gibbs energy of the association (Δ G °) in acetonitrile solutions were calculated based on conductometric data by the Lee-Wheaton method.
Žurnal obŝej himii. 2023;93(4):593-601
593-601
Synthesis, structure, and biological activity of new metal carboxylate complexes containing a glycoluril fragment
Abstract
Cu(II), Ni(II), Zn(II), Co(II), Fe(II), Mn(II) carboxylates containing a pharmacophoric glycoluril fragment were obtained for the first time. The proposed structure of the complexes was established using elemental analysis, spectral methods, and magnetochemistry. Structure of one of the copper(II) complexes was proved by X-ray diffraction analysis. Antibacterial and fungicidal activity of all the compounds was studied. It was shown that the starting acids are inactive, while some complexes exhibit antibacterial activity.
Žurnal obŝej himii. 2023;93(4):602-609
602-609
Quantum-chemical study of the structure of amidinyltetramethoxycarbonylcyclopentadiene and its Hg(II) and Tl(I) complexes
Abstract
DFT CAM-B3LYP/6-311++G(d,p) and CAM-B3LYP/6-311++G(d,p)/SDD calculations showed that the polydentate amidinyltetramethoxycarbonylcyclopentadienyl ligand and its Hg(II) and Tl(I) complexes are the most stable in the form of ylide isomers, in which the hydrogen or metal atom is bonded to the terminal nitrogen atom of the amidinium fragment and in the case of metal complexes, it is additionally coordinated by the π -system of the cyclopentadiene ring. Alternative isomers in which hydrogen or metal atoms are bonded to carbon atoms of the cyclopentadiene ring or to carbonyl oxygen atoms of methoxycarbonyl substituents are energetically less stable at Δ E ZPE = 4.1-15.1 kcal/mol.
Žurnal obŝej himii. 2023;93(4):610-621
610-621
Synthesis and study of dense materials in the Zr–Al–C system
Abstract
The initial powders Zr, Al, C and Zr, Al, Sc were used for the synthesis of MAX phases of the composition Zr2AlC and Zr3AlC2. The highest content (50.4 vol%) of the MAX phase Zr3AlC2 was obtained using the initial powders Zr/Al/Zr in the ratio of components 1:1.5:2 with the addition of 5 vol% Al. The optimal temperature for the synthesis of a material based on the MAX phase Zr2AlC is 1525° C, a material based on Zr3AlC2 is 1575°C. The structure of the synthesized MAX materials obtained includes elongated grains of the composition Zr2AlC and Zr3AlC2, which determines their high strength. Zirconium carbide, as an intermediate phase, is always present in the final products. Due to the large evaporation of aluminum, the ZrO2 phase is also present in the synthesis products. Excess aluminum contributes to the greatest formation of Zr2AlC and Zr3AlC2 phases during synthesis.
Žurnal obŝej himii. 2023;93(4):622-627
622-627
Peculiarities of oxidation of nanoporous iron produced by ferromanganese dealloying in molten salt
Abstract
A wuestite phase metastable at room temperature in the form of a whisker conglomerate was found on the surface of nanoporous iron obtained by electrochemical dealloying (selective anodic dissolution of a less noble metal) of ferromanganese. The features of the further oxidation of iron by TG-DSC and Х-ray phase analysis with a temperature sweep were studied. A wide range of coexistence of three forms of iron oxides and relative stability of the magnetite phase up to 900°C were described.
Žurnal obŝej himii. 2023;93(4):628-634
628-634
Composite films based on polyacrylonitrile and detonation nanodiamonds
Abstract
The properties of composite films based on polyacrylonitrile and detonation nanodiamonds were studied. It was established that the surface properties of the films (roughness and free surface energy) do not change when nanodiamonds are added. It was shown by autoradiography technique with tritium-labeled nanodiamonds that the distribution of particles in a film depends on the modification of their surface. Additives of particles and heat treatment affect the mechanical behaviour of the films, the samples become more brittle. Modification of the nanodiamonds with perfluorononanoic acid leads to a decrease in the strength of the films.
Žurnal obŝej himii. 2023;93(4):635-643
635-643
Structure and stability of group 13/15 hydrides stabilized by Lewis acids and Lewis bases
Abstract
Structural and thermodynamic characteristics of donor-acceptor complexes LA·E′H2EH2·LB(E = B, Al, Ga; E′ = P, As, Sb; LB = SMe2, NMe3);LA- Lewis acids of group 13 elements ER3 (E = B, Al, Ga; R = H, Me, F, Cl, Br, I, C6F5) and transition metal carbonyls Fe(CO)4, M(CO)5, (M = Cr, Mo, W), CpMn(CO)2 were computed by quantum chemical B3LYP-D3/def2-TZVP method. It is shown that removal of the Lewis base is less endothermic than removal of Lewis acid. Stability trends of the complexes depending on group 13/15 elements and Lewis acids were established. Tungsten pentacarbonyl has the highest stabilization effect.
Žurnal obŝej himii. 2023;93(4):644-653
644-653
A practical synthesis of 1-[3-(trimethoxysilyl)propyl]-1H-imidazole
Abstract
A simple and effective method for the synthesis of 1-[3-(trimethoxysilyl)propyl]-1 H -imidazole was proposed by alkylation of sodium imidazolyl obtained from imidazole and sodium hydroxide with (3-chloropropyl)trimethoxysilane at reflux in toluene for 15 h. The target imidazole was obtained with a yield of 82%.
Žurnal obŝej himii. 2023;93(4):654-656
654-656