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Том 89, № 1 (2019)
- Жылы: 2019
- Мақалалар: 32
- URL: https://journals.rcsi.science/1070-3632/issue/view/13706
Article
Synthesis, Structure, and Biological Activity of (2Z)-2-[(2,4-Dinitrophenyl)hydrazinylidene]butanedioic Acid Esters
Аннотация
Dialkyl (2Z)-2-[(2,4-dinitrophenyl)hydrazinylidene]butanedioates have been synthesized by reaction of dialkyl (2Z)-2-hydroxybut-2-enedioates with 2,4-dinitrophenylhydrazine, and their structure has been studied by IR and 1H NMR spectroscopy, mass spectrometry, and X-ray analysis.
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Synthesis and Structure of Biologically Active 1,2-Bis(2-oxocycloalkyl)ethane-1,2-diones and 3,4-Dioxo-4-(2-oxocycloalkyl)butanoic Acid Esters
Аннотация
A two-step procedure has been proposed for the synthesis of 1,2-bis(2-oxocycloalkyl)ethane-1,2-diones and 3,4-dioxo-4-(2-oxocycloalkyl)butanoic acid esters by condensation of cycloalkyl ketones with dimethyl oxalate or of alkyl acetates with dialkyl oxalates and cycloalkyl ketones, respectively. The structure of the synthesized compounds has been discussed on the basis of their IR, 1H NMR, and mass spectra, and their antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Salmonella typhimurium strains has been estimated.
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Quantum Chemistry, NMR Spectroscopy, and Single-Crystal Diffractometry Methods in the Analysis of Protonation Pathways of 2-Amino-4-benzylsulfanyl-6-methylpyrimidines
Аннотация
Protonation pathways of 2-amino-4-benzylsulfanyl-6-methylpyrimidines have been investigated by means of semiempirical PM3 quantum-chemical simulation, 13C NMR spectroscopy, and single-crystal diffractometry methods. In the gas phase and in the bipolar aprotic solvent, the protonation involves the N1 atom. The protonation in the crystalline state is characterized by the formation of a branched system of H-bonds, involving the protons of the amino group besides the mentioned nitrogen atom.
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Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Hydroxycyclohexanones
Аннотация
The reaction of 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with 3-aryl-5-hydroxy-5- methyl-2,4-di(ethoxycarbonyl)cyclohexanones in acetic acid furnished previously unknown 4,5,6,7,8,9-hexahydropyrazolo[1,5-a]quinazoline derivatives.
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Synthesis of N-Substituted Thiazacycloalkanes by Cyclothiomethylation of Primary Aliphatic Amines and Amino Derivatives of Maleopimaric Acid
Аннотация
Three-component cyclocondensation of primary aliphatic amines and amino derivatives of maleopimaric acid methyl ester with formaldehyde and carbochain (1,2-ethane-, 1,3-propane-, 1,4-butane-, 1,5-pentane-, 1,6-hexanedithiols) α,ω-dithiols or 3,6-dioxa-1,8-octanedithiol produced N-substituted thiazacycloalkanes.
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Synthesis of New Thiazolo[3,2-b][1,2,4]triazole Derivatives and Preliminary Evaluation of Their Biological Activity
Аннотация
Heterocyclization of 3-[(1H-1,2,4-triazol-3-yl)thio]pentane-2,4-dione afforded 1-(6-methylthiazolo[3,2-b][1,2,4]-triazol-5-yl)ethan-1-one, the reactions of which with hydroxylamine, hydrazincarboxamide, hydrazincarbothioamide, hydrazine hydrate and para-toluenesulfonyl hydrazide resulted in the formation of the corresponding derivatives. 1-(6-Methylthiazolo[3,2-b][1,2,4]triazol-5-yl)ethan-1-one oxime reacted with alkyl halides and phenyl isocyanate to produce the corresponding O-alkyl- and O-phenylcarbamoyl derivatives. The growth regulating activity of the compounds obtained was studied.
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2-(Fur-2-yl)thiazolo[4,5-f]quinoline: Synthesis and Electrophilic Substitution Reactions
Аннотация
Condensation of quinoline-5-amine with furan-2-carbonyl chloride in propan-2-ol afforded N-(5- quinolyl)furan-2-carboxamide, treatment of which with an excess of P2S5 in anhydrous pyridine led to the formation of the corresponding thioamide. Oxidation of the latter with potassium ferricyanide in an alkaline medium furnished 2-(fur-2-yl)thiazolo[4,5-f]quinoline. A plausible mechanism for its formation was proposed. The reactions of electrophilic substitution (nitration, bromination, formylation, acylation) of the obtained N-(5-quinolyl)furan-2-carboxamide were studied.
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Synthesis and Transformations of 5-Substituted 2-Furoyl Phosphonates
Аннотация
5-Chloromethyl-2-furoyl chloride when treated with triethyl phosphite has given 5-chloromethyl-2-furoyl phosphonate. This compound has reacted with sodium azide in the presence of potassium iodide to give 5-azidomethyl-2-furoyl phosphonate. Treatment of 5-chloromethyl-2-furoyl phosphonate with secondary amines even under mild conditions has caused cleavage of P–C bond with liberation of diethyl hydrogen phosphite and formation of 5-chloromethyl-2-furancarboxamide. Butanthiol in the presence of potassium carbonate in acetonitrile has converted the chloromethyl group into the butylthiomethyl one and simultaneously split the P–C bond with the formation of the corresponding thioester. Under the action of S-methylthiuronium iodide and triethylamine, 5-chloromethyl-2-furoyl phosphonate has been unexpectedly reduced into the 5-methyl derivative. 5-Butylthiomethyl- and 4-(N-morpholinomethyl)-2-furoul chlorides have been phosphorylated with triethyl phosphite into the corresponding 5-functionalized 2-furoyl phosphonates. The prepared furoyl phosphonates have reacted with resonance-stabilized phosphoranes to give phosphorylated derivatives of 3-(furyl)acrylates and 4-(furyl)but-3-en-2-one with trans-location of phosphoryl and carbonyl groups with respect to the double bond.
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Reaction of 3a,6a-Diaza-1,4-diphosphapentalene with Substituted Acetylenes
Аннотация
The reaction of 3a,6a-diaza-1,4-diphosphapentalene with 1-bromo-2-phenylacetylene has led to the formation of 1,1-bis(phenylethynyl)- and 1,4-dibromo-3a,6a-diaza-1,4-diphosphapentalene. The first has been also prepared via a different route by the reaction of 1,4-dichloro-3a,6a-diaza-1,4-diphosphapentalene with lithium phenylacetylenide in 96% yield. No isomeric 1,4-bis(phenylethynyl)-DDP has been formed in this reaction. The reaction in the 3a,6a-diaza-1,4-diphosphapentalene–[Ph3PC≡CPh]Br–carbazole three-component system proceeds as addition of carbazole to the initially formed complex of 3a,6a-diaza-1,4-diphosphapentalene with [Ph3PC≡CPh]Br with the rupture of the P–N bond. The products and intermediates of the reaction have been simulated by B3LYP/6-31+G(d) method.
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Phosphorylation of Acetylaminophenols with Secondary Phosphine Chalcogenides: Synthesis of O-(Acetylamino)phenyl Chalcogenophosphinates
Аннотация
Oxidative cross-coupling of 4-acetylaminophenol (paracetamol) and its structural isomers (2- and 3-acetylaminophenols) with secondary phosphine chalcogenides at room temperature in the CCl4–Et3N system produced O-(acetylamino)phenyl chalcogeneophosphinates in a 80% yield.
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Synthesis and Properties of [4-(Diethylamino)phenyl]dichlorophosphine
Аннотация
[4-(Diethylamino)phenyl]dichlorophosphine synthesized for the first time has reacted with trialkyl orthoformate and ethylene oxide in the presence of ethyl chloroacetate with the formation of phosphorylated formals and ethyl [4-(diethylamino)phenyl](2-chloroethoxy)phosphonyl acetate, a precursor of a new analog of nootropic drug KAPAKh.
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Synthesis, Structure, and Biological Activity of Magnesium(II), Zinc(II), Cobalt(II), and Copper(II) Bis(4-aryl-1-ethoxy-1-oxobutane-2,4-dionates)
Аннотация
The condensation of aryl methyl ketones with diethyl oxalate in the presence of metallic sodium or sodium hydride gave sodium 4-aryl-1-ethoxy-1,4-dioxobut-2-en-2-olates, and metal exchange of the latter with magnesium(II), zinc(II), cobalt(II), and copper(II) salts afforded the corresponding metal bis(4-aryl-1-ethoxy-1-oxobutane-2,4-dionates). The obtained complexes were tested for antibacterial activity against gram-positive and gram-negative bacteria by the agar diffusion method.
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Synthesis and Properties of Calcium, Strontium, and Barium Uranates
Аннотация
Pure crystalline compounds MIIU3O10 · n H2O (MII = Ca, Sr) and BaU2O7 · 3 H2O were obtained by reactions of synthetic schoepite (UO3 · 2.25 H2O) with aqueous solutions of calcium, strontium, and barium nitrates under hydrothermal conditions at 200°C and pH 7‒8. Their structure, dehydration, and thermal decomposition were studied by chemical analysis, X-ray fluorescence spectrometry, X-ray powder diffraction, IR spectroscopy, and thermogravimetric analysis.
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Synthesis and Structure of μ2-Oxobis(carboxylatotriarylantimony)
Аннотация
Binuclear antimony compounds with a bridging oxygen atom [Ph3SbOC(O)R]2O (R = CF2CF3, CF2CF2CF3), [(4-МеC6H4)3SbOC(O)CF2CF3]2O, [(3-FC6H4)3SbOC(O)R]2O (R = C6F5, CF2CF3) have been synthesized by reacting equimolar amounts of triarylantimony, carboxylic acid and tert-butyl hydroperoxide in diethyl ether. According to X-ray diffraction data, in the molecules of compounds obtained, the Sb atoms have a trigonal bipyramid coordination with carboxylate ligands and a bridging oxygen atom in axial positions. The intramolecular distances Sb···O with a carbonyl oxygen atom are less than the sum of the van der Waals radii of Sb and O by ~0.2–0.4 Å.
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Luminescent Complexes of Zn(II) and Cd(II) with Chiral Ligands Containing 1,10-Phenanthroline and Natural Monoterpenoids (+)-3-Carene or (+)-Limonene Fragments
Аннотация
New chiral 1,10-phenanthroline-derived ligands containing fragments of (+)-3-carene (L1) and (+)-limonene (L2) natural monoterpenoids and their complexes Zn(L1,2)Cl2·1.5H2O, Cd(L1,2)Cl2·nH2O, Zn(L1)Br2·2H2O, and Cd(L1)Br2·2H2O were synthesized. According to NMR and IR spectroscopy data, a conclusion was made about the polynuclear structure of the compounds obtained. Luminescent properties of the compounds obtained were investigated. Lifetimes of the excited states and luminescence quantum yields (φf) were determined. For free ligands, blue fluorescence was observed. In the case of Zn(II) and Cd(II) complexes, luminescence appeared in the green region of the spectrum.
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Synthesis of Symmetrical Polyamide–Sulfonimides Based on Bis-saccharin Dicarboxylic Acid Dichlorides
Аннотация
Polycondensation of ethylene-bridged bis(saccharincarbonyl chlorides) with aliphatic diamines afforded soluble polyamide–sulfonimides. The effects of the concentration of the initial reactants and reaction temperature on the yield and intrinsic viscosity of the obtained polymers were studied, and optimal conditions for their synthesis were found. According to the DTA and TGA data, the synthesized polymers are characterized by a high heat resistance and can operate at elevated temperature.
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Synthesis of Cu@Ag Nanoparticles with a Core–Shell Structure Stabilized with Oxyethylated Carboxylic Acid
Аннотация
Bimetallic Cu@Ag nanoparticles with a core–shell structure were synthesized by reduction of copper 2-[2-(2-methoxyethoxy)ethoxy]acetate with hydrazine hydrate in benzyl alcohol, followed by reducing the silver ions on the copper surface by transmetallation reaction. The sinthesized nanoparticles were characterized by X-ray diffraction, transmission electron microscopy, and optical spectroscopy methods. The effect of the synthesis conditions such as temperature, time, Ag: Cu molar ratio, the rate of silver nitrate addition, on the uniformity of silver coating on the surface of copper nuclei was studied.
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Photochemical Synthesis of Cu2O and Cu2O/Ag Nanoparticles in Polyols
Аннотация
Cu2O nanoparticles were synthesized by photoreduction of copper(II) complex compounds with ethylene glycol and glycerin in the photolite volume. Their optical properties, morphology, phase composition, and photocatalytic activity in methyl orange decomposition were studied. The electrochemical substitution reaction afforded Cu2O/Ag composite nanoparticles. Their increased activity in photodegradation reactions of methyl orange in comparison with unmodified Cu2O particles was found.
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Radiation-Chemical Reduction of Copper Ions in Nanoporous Matrices Based on High-Density Polyethylene
Аннотация
The effect of preliminary annealing of semicrsytalline high-density polyethylene films on the parameters of nanoporous structure formed during deformation of polymers in physically active liquid environments via the intercrystallite crazing has been studied. Optimal conditions providing the development of a stable open-cell polymeric materials with a high level of porosity (50%) and pore size below 10 nm have been elavorated. For the first time, the in situ reduction of copper ions into copper(0) in the pores of the highdensity polyethylene nanoporous polymer matrix has been carried out using the radiation-chemical reduction method. The reaction has led to the formation of nanoscale copper particles within the polymer, which makes it possible to produce metal-polymer nanocomposites with valuable functional properties.
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Cadmium Naphthalenedisulfonate Complex as Heterogeneous Catalyst in the Knoevenagel Condensation
Аннотация
The reaction of naphthalene-1,5-disulfonate (1,5-nds), 2,4,5-tris(pyridin-4-yl)imidazole (tpim), and cadmium(II) acetate dihydrate Cd(OAc)2·2H2O afforded a 2D coordination polymer, [Cd(tpim)(1,5-nds)]n (1). Crystal structure analysis of the obtained complex showed the presence of its molecule of uncoordinated pyridyl groups as active organic sites. The complex was found to act as efficient and reusable heterogeneous catalyst in the Knoevenagel condensation. Its stability under the reaction conditions was confirmed by comparison of the powder X-ray diffraction patterns of the fresh and reused catalysts.
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Synthesis and Molecular Docking Studies of Novel 5-Arylideneaminouracils
Аннотация
A series of novel 5-arylideneaminouracils is synthesized from 5-aminouracil and substituted salicylaldehydes, and characterized by spectroscopic methods. DNA interactions of model molecules are explored using molecular docking simulations that reveal that these types of molecules can act as DNA groove binders.
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Synthesis and Antitumor Activity of Some New Fused Heterocyclic Compounds
Аннотация
Reaction of thiopyrimidine derivative 3 with hydrozonoyl chlorides 4a–4e gives new fused heterocyclic compounds 7a–7e containing triazole ring. The latter demonstrates a wide range of biological activities. Thiazolone pyridopyrimidines 8, 9a, 9b are prepared by the reaction of thiopyrimidines with chloroacetic acid and different aromatic aldehydes in the presence of acetic anhydride. Bis-arylidene 2 reacts with malononitrile or ethyl cyanoacetate with formation of carbonitrile derivatives 10, 11. Reaction of bisarylidene 2 with phenyl hydrazine and hydrazine hydrate leads to diazole derivatives 12, 13. Structures of the new compounds are elucidated from IR, 1H and 13C NMR, and mass spectra. All newly synthesized products are tested for antitumor activity on three human tumor cell lines, including prostatic adenocarcinoma (PC3), human colorectal carcinoma (HCT116), human liver hepatocellular carcinoma (HepG2) and breast carcinoma (MCF7). Compounds 2, 7a–7d demonstrate the considerable potency.
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Synthesis and Physical Characterization of β-Alkyl Oligoselenophenes
Аннотация
α-Conjugated oligoselenophenes are characterized by very low solubility in organic solvents. Their higher solubility may be achieved by introducing alkyl side chains into the β-positions of selenophene moieties. For the first time, β,β′-dihexyl sexiselenophene is synthesized according to the conventional approach. Physical and electrochemical studies of β,β′-dialkyl oligomers are analyzed and compared with corresponding thienyl oligomers.
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Selective Complexation of Hydrazone Based Ketimine with 3d, 4d, and 5d Metals: Synthesis, Characterization, and Biological Activity
Аннотация
The hydrazone derived ketimine of dehydroacetic acid and its metal {Cu(II), Ni(II), Zn(II), Fe(III), Cd(II), Pd(II), La(III), Nd(III), Ce(III)} complexes are synthesized and characterized by IR, 1H and 13C NMR, and UV-Vis spectroscopy. DNA studies have been carried out for metal complexes by electronic absorption spectroscopy. It is determined that metal complexes bind to DNA through intercalation. The complexes of Cu(II), Zn(II) and Pd(II) demonstrate significant activity against HeLa cells (cervical cancer).
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Letters to the Editor
Reactions of Lithium Acylates α-Carbanions with 1,2-Diiodoethane
Аннотация
The interaction of lithium acylates α-carbanions (obtained via metallation of acetic, butyric, and isobutyric acids with lithium diisopropylamide) with 1,2-diiodoethane under argon in tetrahydrofuran at 20–25°C has proceeded as oxidative cross-coupling of enolate anions to form succinic, 2,3-diethylsuccinic, and 2,2,3,3-tetramethylsuccinic acids with yields 50, 53, and 16%, respectively. The products of sequential nucleophilic substitution of iodine atoms with alkyloxycarbonyl species have not been detected.
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Synthesis of 5-Methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one in Supercritical Carbon Dioxide
Аннотация
5-Methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one, an intermediate product in the synthesis of the antiviral drug Triazid®, was obtained for the first time by condensation of 3H-1,2,4-triazol-5-amine with ethyl acetoacetate in the presence of a catalytic amount of ZnCl2 in supercritical carbon dioxide (200 bar) under solvent-free conditions. Depending on the temperature and reaction time, the conversion was 90%.
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Methyl Trifluoropyruvate in Cyclocondensation Reactions with N-Substituted Ureas
Аннотация
The transformations of methyl trifluoropyruvate in cyclocondensation reactions with N-substituted ureas, leading to 3-substituted 5-hydroxy- or 5-methoxy-5-trifluoromethylimidazolidine-2,4-diones, were studied. The possibility of using 5-hydroxy-3-(prop-2-in-1-yl)-5-trifluoromethylimidazolidine-2,4-dione for modifying phenothiazine with a copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition was shown.
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Synthesis and Antibacterial Activity of New N9-Substituted Acridine-9-amines
Аннотация
A method for the synthesis of N9-substituted acridine-9-amines by reacting 9-chloroacridines with 2-(2-methyl-5- nitro-1H-imidazol-1-yl)ethanamine was developed. The synthesized compounds showed high antibacterial ability against B. subtilis bacteria compared with rivanol and metronidazole.
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α-Azidoalkylphosphonate in 1,3-Dipolar Cycloaddition with Propargyl-Containing Pharmacophores
Аннотация
Copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition reactions of α-azidoalkylphosphonates with propargyl-containing pharmacophores such as phenothiazine, tetrahydro-γ-carboline, tetrahydrocarbazole, carbazole and 3,5-dimethyl-1-aminoadamantanes led to the formation of the corresponding 1, 4-substituted 1,2,3-triazoles and make it possible to introduce a diethoxyphosphorylalkyl fragment into the molecules of potential neuroprotectors using a triazole-containing spacer.
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Quantum-Chemical Modeling of the First Coordination Sphere of the Metal Cation in Monazite
Аннотация
A model of minimum size clusters in orthophosphates has been suggested. In the case of monazite, the cluster includes a cerium(III) cation with nine oxygen atoms of the first coordination sphere, from seven neighboring phosphate anions. Its charge consists of the cation charge QM and the charges of the oxygen atoms QO =–1 a. u. The results of quantum-chemical simulation assume the possibility of the Ce(III) cation substitution with the Th(III), Th(IV) and U(IV) actinide cations. Substitution with thorium is favorable over that with uranium.
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