Том 89, № 9 (2019)
- Год: 2019
- Статей: 35
- URL: https://journals.rcsi.science/1070-3632/issue/view/13714
Article
Alkaline Hydrolysis of 3-(2-Arylhydrazinylidene)-2,4-dioxoalkanoates
Аннотация
Alkaline hydrolysis of 3-(2-arylhydrazinylidene)-2,4-dioxoalkanoic acids (obtained by azo coupling of the condensation products of the corresponding ketones and dialkyl oxalates in the presence of sodium) afforded 3-(2-arylhydrazinylidene)-2,4-dioxoalkanoic acids. Antimicrobial activity of some of the synthesized acids against gram-positive and gram-negative bacteria was evaluated.
Synthesis and Reactions of 2,2-Dichlorocyclopropylmethyl-4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoate with Secondary Amines
Аннотация
The reaction of potassium 4-aminobenzoate with 2-bromomethyl-1,1-dichlorocyclopropane proceeds regioselectively with the retention of a three-membered ring and leads to the formation of 2,2-dichlorocyclo-propylmethyl 4-aminobenzoate. The reaction of 2,2-dichlorocyclopropylmethyl 4-aminobenzoate with maleic anhydride and intramolecular cyclization of the resulting amide in the presence of p-toluenesulfonic acid yields 2,2-dichlorocyclopropylmethyl-4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)benzoate. Secondary amines are attached at the double bond of the synthesized maleimide with the formation of 2,2-dichlorocyclopropylmethyl-4-[(3-R2N-2,5-dioxo-2,3,4,5-tetrahydro-1H-pyrrolyl)]benzoates.
Synthesis and Properties of New Fluorine-Containing Thieno[2,3-b]pyridine Derivatives
Аннотация
Cyanothioacetamide reacted with 1,1,5,5-tetrafluoroacetylacetone to give 4,6-bis(difluoromethyl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile, and alkylation of the latter with α-chloroacetamides afforded 3-amino-4,6-bis(difluoromethyl)thieno[2,3-b]pyridine-2-carboxamides. The structure of the key compounds was proved using two-dimensional NMR techniques. In silico analysis of potential biological activity and bioavailability of the synthesized compounds was performed.
Unexpected Result of Thiophosphorylation of 6-Aminopyrano[2,3-c]pyrazole-5-carbonitrile Derivative
Аннотация
The reaction of 6-amino-3-methyl-4-(2,4-dichlorophenyl)-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with phosphorus sulfide in boiling pyridine unexpectedly leads to the formation of a not previously described heterocyclic system—[1,2]oxaphosphinino[6,5-c]pyrazole derivative. Structure of the obtained compound was proved using 2D NMR spectroscopy and X-ray diffraction analysis.
Skeletal Diversity in Catalytic Synthesis of (1,3-Oxazacycloalk-3-ylmethyl)-Substituted Pyrroles
Аннотация
A series of bi- and trinuclear pyrrole derivatives was prepared by the 5 mol % ZrOCl2 ·8H2O-catalyzed CH-sp2-aminomethylation reaction of pyrrole with bis(1,3-oxazacycloalk-3-yl)methanes. The reaction proceeds at the positions 2, 5 or 2 of pyrrole depending on the amount of aminomethylating reagents obtained from formaldehyde and α,ω-amino alcohols (2-aminoethan-1-ol, 3-aminopropan-1-ol, 4-aminobutan-1-ol). The aminomethylation reaction of indole with bis(1,3-oxazolidin-3-yl)methane proceeds at the position 3. In the case of carbazole, N-aminomethylation proceeds under these conditions.
Reactions of 2-Phosphonylethynylated 2-(Arylamino)malonates with Some Bases
Аннотация
The reaction of dialkyl 2-[(dialkoxyphosphoryl)ethynyl]-2-(arylamino)malonates with bases (CH3COOK, t-BuOK) can serve as a method for preparing original diphosphonylated 2,3-dihydro-1H-pyrroles and 4-phosphonylated 1-azabuta-1,3-dienes. A probable scheme for the formation of the obtained new compounds is proposed.
Transesterification of Exocyclic Ester Group of Methyl Pheophorbide a
Аннотация
The reaction of methyl pheophorbide a with various alcohols in toluene in the presence of dimethylaminopyridine as a base was investigated. Under these conditions, a chemoselective transesterification of the exocyclic ring proceeds without the use of an activating agent (N-methyl-2-chloropyridinium iodide) or a catalyst (molecular iodine).
Elucidation of the Structure of Products of Triphenylphosphine Electrooxidation in the Presence of Camphene
Аннотация
The structure of the products of anodic oxidation of triphenylphosphine in the presence of camphene carried out in acetonitrile with sodium perchlorate as supporting electrolyte has been studied. The major product, triphenylphosphine oxide, has been isolated from the solution in the form of cocrystals of free triphenylphosphine oxide and its complex with sodium perchlorate. The molecular structure of the cocrystals has been studied by X-ray diffraction analysis. Triphenylcamphenylphosphonium perchlorate, bornylacetamide, and a terpene compound with triphenylphosphonium and acetamide substituents in the cycle have been detected by NMR 13C as the electrolysis side products.
Negative Photochromism of Solutions of Functionalized Spiropyrans in a Water—Acetonitrile Mixture
Аннотация
A spectral-kinetic study of photochromic functionalized nitro-substituted indoline spiropyrans in water-acetonitrile mixtures has allowed to observe for the first time the effect of negative photochromism due to the self-assembly of photochromic molecules in a mixed solvent with the formation of hydrogen bonds and proton complexes.
Effect of the Nature of Organic Solvent on the Association of N-[3-(Dimethylamino)propyl](meth)acrylamides
Аннотация
The association of N-[3-(dimethylamino)propyl](meth)acrylamides in tetrachloromethane, tetrahydrofuran, and N, N-dimethylformamide has been studied by means of IR spectroscopy and quantum-chemical simulation at the B3LYP/6-31+G(d,p)/PCM level. The effect of the hydrogen bonding capacity of the solvent on the degree of participation of N-[3-(dimethylamino)propyl](meth)acrylamides in hydrogen bonding with the formation of the amide-solvent type self-associates and heteroassociates has been elucidated.
Influence of Nanotubes on the Relative Stability of Orthogonal Form of Dialane
Аннотация
Conformational transformations of the orthogonal and planar forms of dialane Al2H4 molecule in model single-walled carbon nanotubes have been studied by the PBE/3ζ DFT method. In most cases, the effect of the nanosystem force field on the encapsulated molecule has been reflected in shortening of the Al–Al and Al–H bonds, decrease in the bond angles, and change in partial charges and bond orders which have resulted in the inversion of the relative stability of the orthogonal and planar forms as well as generation of high negative charge on the molecule of Al2H4 in the nanotube cavity. The decisive effect of the molecular orbital energy of the dialane@nanotube cluster on the stabilization of the planar conformation has been concluded.
Synthesis and Selected Properties of Novel Metal Complexes with Bis-Azomethine Based on 7-Hydroxy-4-methyl-8-formylcoumarin and 1,3-Diaminopropan-2-ol
Аннотация
Condensation of 7-hydroxy-4-methyl-8-formylcoumarin with 1,3-diaminopropan-2-ol has afforded a novel bis-azomethine, and its metal chelates with copper(II), nickel(II), and zinc(II) have been obtained. Structure and properties of the prepared compound have been studied by spectral and quantum-chemical methods.
Synthesis and Structure of Chloro Complex of Palladium(II) with {[6-Amino-2-(butylsulfanyl)pyrimidin-4-yl]oxy}acetic Acid
Аннотация
Palladium(II) chloro complex with {[6-amino-2-(butylsulfanyl)pyrimidin-4-yl]oxy}acetic acid has been synthesized via the ligand substitution method. Composition and structure of the coordination compound have been elucidated from the combined data of elemental analysis and spectroscopy. The coordination of {[6-amino-2-(butylsulfanyl)pyrimidin-4-yl]oxy}acetic acid occurs via the formation of a donor-acceptor bond between the palladium(II) ion and the nitrogen atoms in position 1 of the pyrimidine rings, chloride ions entering the inner coordination sphere of the PdCl2L2 complex, to give trans-bis({[6-amino-2-(butylsulfanyl)pyrimidin-4-yl]oxy}-hydroxyacetyl)dichloropalladium(II).
Synthesis and Structure of Hexachloroplatinate Complexes
Аннотация
The reactions of tetraorganylphosphonium and trimethylammonium chlorides with hexachloroplatinic acid hydrate in an acetonitrile–diethyl sulfoxide solution produced [Ph3PCH=CHCH3]2[PtCl6], [Ph3PCH2OCH3]2[PtCl6], and [Me3NH]2[PtCl6] complexes. The structure of the resultant platinum complexes was examined by X-ray diffraction analysis.
Temperature Dependences of the Saturated Vapor Pressure of Lantanum Complexes Based on 2-(2-Benzoxazol-2-yl)phenolate Ligand
Аннотация
Temperature dependences of the saturated vapor pressure of lanthanum complexes based on 2-(2-benzoxazol-2-yl)phenolate ligand have been obtained using the Knudsen effusion method. The thermodynamic parameters of vaporization have been calculated from the p−T data. Mass spectra and differential scanning calorimetry data have been obtained.
Special Features of Sorption and Luminescence of Tb3+ Cations and Azomethine Bases in Perfluorosulfonic Membrane
Аннотация
The limiting value of ion-exchange sorption capacity of the perfluorosulfonic membrane with respect to Tb3+ is reproducible when the cation is in excess in the solution. Modification of the membrane with azomethine bases is facilitated by the high diffusion mobility of the molecules and proceeds with the formation of strong surface compounds. The manifestation of coexisting emission centers in the Tb3+-modified membrane treated with azomethine is determined by the energy of the exciting light.
Extraction of Rare-Earth Elements(III) with Mixtures of 1-Phenyl-3-methyl-4-benzoyl-5-pyrazolone and Phosphoryl-Containing Podands
Аннотация
Extraction of rare-earth elements(III) ions from chloride solutions with mixtures of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and phosphoryl-containing podands in organic solvents has been studied. The observed significant synergistic effect is associated with the formation of hydrophobic mixed-ligand complexes of rare-earth elements(III). The stoichiometry of the extracted complexes has been determined, and the extraction constants have been calculated. The influence of the phosphoryl-containing podand structure, the organic solvent nature, and the aqueous phase composition on the efficiency of the extraction of rare-earth element(III) ions into the organic phase has been considered.
Thermodynamic Modeling of the Stage of Polychlorinated Biphenyls Preparation to Thermal Decomposition
Аннотация
The reaction of Sovol (technical mixture of polychlorinated biphenyls) with sodium methoxide in dimethyl sulfoxide and methanol has been studied using the thermodynamic modeling method. The optimal process conditions have been elaborated: 1 atm, 115°C, 0.25 mol of dimethyl sulfoxide, 0.085 mol of methanol, the polychlorinated biphenyls: sodium methoxide molar ratio = 1: 4. Experimental data on the interaction of the polychlorinated biphenyls with sodium methoxide under the theoretically determined conditions have revealed a range of positive effects: savings of the reactants, complete conversion, and the formation of potentially less toxic compounds. The studied interaction can serve as a stage for the pretreatment of toxic polychlorinated biphenyls for the pyrolytic destruction.
Formation of Bi1−xCaxFeO3−δ Nanocrystals via Glycine-Nitrate Combustion
Аннотация
The features of the formation of nanocrystals in the BiFeO3–CaFeO3 system via glycine-nitrate combustion were studied. The crystallite size of the bismuth orthoferrite-based solid solutions (20–45 nm), as well as their particle size, were found to depend on the calcium content. The formation processes were activated in the temperature range corresponding to the melting of the surface (nonautonomous) phase.
Synthesis, Biological Activity, and Molecular Docking Assessment of Some New Sulfonylated Tetrazole Derivatives
Аннотация
The designed molecular structures have been subjected to computational analysis for calculating their physicochemical properties and drug likeness. The calculated data indicate that most of the compound possess the bioactivity score in the active zone. Synthetic approach to the target compounds is straightforward and easy to handle. Structures of the new compounds are supported by FT-IR, 1H, and 13C NMR, and mass spectra. Antimicrobial tests of the products against pathogens (S. aureus, S. epidermidis, E. coli, and P. mirabilis) indicate the products as active or highly active. Their cyto-toxicity is determined to be 92–98% at concentration of 3.125 µmol/L. The molecular docking analysis carried out for the target compounds against the receptor Glc-N-6P exhibits low binding energy and various binding sites of those.
Design, Synthesis, and Biological Activity of New Bis-1,2,3-triazole Derivatives Bearing Thiophene-Chalcone Moiety
Аннотация
A series of novel 1,4-substituted bis-aralkyl and aryl 1,2,3-triazoles bearing thiophene chalcones are synthesized via the Claisen condensation of bis propargyl acetophenone intermediate with thiophene-2-carboxaldehyde followed by the Huisgen cycloaddition of the accumulated bis propargyl chalcone intermediate with various aryl and aralkyl azides. Structures of the synthesized compounds are characterized by IR, NMR and mass spectroscopy. The products are tested for antimicrobial and antioxidant activities, and some of those exhibit antibacterial and antifungal activity. The moderate to poor DPPH free radical scavenging activity is determined for some products.
Synthesis, Type II Diabetes Inhibitory Activity, and Antimicrobial Tests of Benzothiazole Derivatives Bridged with Indenedione by Methylenehydrazone
Аннотация
Benzothiazolyl hydrazones are synthesized and tested as hypoglycemic and antimicrobial agents. Condensation of 2-acyl-(1H)-indene-1,3(2H)-diones with 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles gives the corresponding hydrazones in high yields. Preliminary biological assay of the products reveals significant antidiabetic and antimicrobial activities. The α-amylase and α-glucosidase inhibition assay is used for determination of Type II diabetes inhibitory activity.
Synthesis, Spectroscopic Studies, and Biological Activity of Some New N2O2 Tetradentate Schiff Base Metal Complexes
Аннотация
The new tetradentate Schiff base N,N′-ethylene bis[1-ethyl-6-fluoro-4-imine-7-(piperazine-1-yl)-quinoline-3-carboxylic acid] (Nor-en) has been synthesized. Its chelated complexes with Co(II), Ni(II), Cu(II), Zn(II), Y(III), Zr(IV), La(III), and U(VI) are characterized using molar conductivity, magnetic moment, FT-IR, UV-Vis, 1H NMR, and mass spectra, and thermal analysis. It is determined that the complexes have monomeric structures and exist in the octahedral configuration. The molar conductance values indicate the electrolytic nature of the complexes. According to the spectroscopic data, the complexes share the same coordination environment around the metal ions, consisting of N2O2 and one or two water molecules. The thermodynamic parameters (activation energy, E*, entropy, ΔS*, enthalpy, ΔH*, and Gibbs free energy, ΔG*) are calculated using Coats-Redfern and Horowitz-Metzger methods. The carried out tests indicate the compounds’ high antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Salmonella typhi. Anticancer activity of the ligand and its metal complexes is evaluated against HepG-2 cells (human Hepatocellular carcinoma) and determined to be very low.
Synthesis and Antimicrobial Activity of (E)-2-[(1-Substituted Phenyl-1H-1,2,3-triazol-4-yl)methylene]-2,3-dihydro-1H-inden-1-ones
Аннотация
A series of novel (E)-2-[(1-phenyl-1H-1,2,3-triazol-4-yl)methylene]-2,3-dihydro-1H-inden-1-one derivatives has been synthesized by condensation of 1-phenyl-1H-1,2,3-triazole-4-carbaldehydes with 2,3-dihydro-1H-inden-1-one. The synthesized compounds are characterized by 1H and 13C NMR, and mass spectrometry, and tested in vitro against four bacterial organism and two fungal organisms. The tests data demonstrate moderate to good activity of the compounds.
Synthesis and Anti-Inflammatory Activity of Some New Pyrimidinothienocinnoline Derivatives
Аннотация
Synthesis of a new series of pyrimidinothienocinnoline derivatives involves the reaction of 9-aminodibenzo[f, h]pyrimido[4′,5′:4,5]thieno[2,3-c]cinnoline-8-carbonitrile with formamide that gives 8-amino-dibenzo[f, h]-pyrimido[4′,5′:4,5]thieno[2,3-c]cinnoline. Reactions of the latter with morpholine, piperidine, malononitrile, phenylbromide, aromatic aldehydes, and ethyl cyanoacetate have been studied. Some synthesized compounds have been subjected to further transformations. The synthesized pyrimidinothienocinnoline derivatives are tested for their anti-inflammatory activity.
Synthesis, Molecular Modeling, and Antiviral Activity of Novel Triazole Nucleosides and Their Analogs
Аннотация
Two new pharmacophoric models incorporating 1,2,3-triazole glycosides have been synthesized in good yields via 1,3-dipolar cycloaddition reaction based on the click strategy. Copper catalyzed click dipolar cycloaddition of the acetylenic centers with azido compounds leads to the targeted compounds. Docking of the designed structures into Influenza virus neuraminidase (NA) active site is studied. Three molecular structures exhibit good fitting inside the binding site of the protein molecule. Antiviral activity against H5N1 avian influenza virus strain A/Egypt/M7217B/2013 is tested, and a number of compounds demonstrate high inhibition activity.
Microwave Assisted Synthesis of 5-[4-(3-Phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl]-1H-tetrazole Derivatives and Their Antimicrobial Activity
Аннотация
In the present study, we report the synthesis of 5-[4-(3-phenyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl]-1H-tetrazole derivatives by the Michael addition of chalcones to hydrazine hydrate in presence of acetic acid under conventional heating and microwave irradiation. All the synthesized compounds are characterized by IR, NMR, and mass spectra. The products are screened for their in vitro antimicrobial activity against strains such as Staphylococcus aurous, Bacillus subtilis, Klebsiella pneumonia, Escherichia coli, Aspergillus Niger, Aspergillus flavus, and Fusarium oxysporum. Most of the compounds exhibit high activity.
Oligoselenophenes (n and p Type): Synthesis and Properties
Аннотация
An array of semiconducting oligoselenophenes (n and p types), up to hexamer units, has been synthesized by the double Stille coupling methods using tetrakis(triphenylphosphine)palladium(0) as a catalyst. A series of semiconducting oligomers (n and p types) containing mixed hetero-units (hexamers of thiophene and selenophene) have been also synthesized using the Stille coupling reaction. Their thermal properties are systematically studied and compared with those of π-conjugated thiophene based oligomers using DSC and TGA. The field-effect mobility of synthesized n and p type oligomers is analyzed.
Letters to the Editor
Synthesis and Intramolecular Heterocyclization of Selected Isonicotinic Acid Thiocarbazides
Аннотация
The reaction of isonicotinic acid hydrazide with ethyl-, allyl-, and cinnamoyl isothiocyanates has afforded the corresponding alkylthiosemicarbazides and the products of their intramolecular heterocyclization, 1,2,4-triazoles.
Electrophilic Tropylation of Aminopyridines and 4-Aminoquinoline
Аннотация
The reactions of 2-, 3-, 4-aminopyridines or 4-aminoquinoline with hydrolytically stable tropylium salts (perchlorate or tetrafluoroborate) have afforded N-(1′-cyclohepta-2′,4′,6′-trienyl)-2-aminopyridine, N-(1′-cyclohepta-2′,4′,6′-trienyl)-3-aminopyridine, N-(1′-cyclohepta-2′,4′, 6′-trienyl)-4-aminopyridine, and N-(1′-cyclohepta-2′,4′,6′-trienyl)-4-aminoquinoline. The effect of imidazole and the tropylium salt anion on the yield and stability of the final reaction products has been studied.
Regio- and Stereoselective Synthesis of (E)-2-Bromo-1-(phenoxymethyl)vinyltellanes
Аннотация
Regio- and stereoselective synthesis of tribromo[(E)-2-bromo-1-(phenoxymethyl)vinyl]tellane based on the reaction of tellurium tetrabromide with propargyl phenyl ether has been elaborated. This reaction is the first example of the addition of TeBr4 to propargyl ethers. Reduction of the product with sodium borohydride has afforded bis[(E)-2-bromo-1-(phenoxymethyl)vinyl]ditellane.
Synthesis of Alkylphosphoryl-Containing 4(5)-Arylimidazolin-2-ones
Аннотация
The acid-catalyzed reaction of {2-[1-(2,2-dimethoxyethyl)-3-(phenylcarboxamido)]ethyl}phosphonate or diethyl [2-(2-oxo-3-phenyl-2,3-dihydro-1H-imidazol-1-yl)ethyl]phosphonate with resorcinol and its derivatives afforded new 4(5)-arylimidazolin-2-ones. The ratio of the resulting regioisomers is significantly affected by the structure of the starting compounds, which allows one to obtain products with a predominance of one regioisomer.
Selected articles originally published in Russian in Rossiiskii Khimicheskii Zhurnal (Russian Chemistry Journal)
Synthesis and Investigation of Copolymers of Glycidyl Methacrylate and Methyl Pheophorbide a in a Solution
Аннотация
Copolymers of glycidyl methacrylate and methyl pheophorbide a of different compositions were synthesized by radical copolymerization in toluene and THF solutions. The influence of the nature of the solvent, initial weight ratio of the monomers, and amount of the copolymerization initiator on the yield of the copolymer and its structure, composition, and properties were established. Physicochemical and molecular weight characteristics of the copolymers were determined.
Mesomorphic and Dielectric Properties of Supramolecular 3,5-Diamino-1-dodecyl-1,2,4-triazole
Аннотация
The formation of a thermotropic smectic phase in 3,5-diamino-1-dodecyl-1,2,4-triazole was revealed by polarizing microscopy and DSC. Depending on heating and cooling conditions, transitions between different types of layered packings occur, which was evidenced by dielectric measurements. Quantum-chemical simulation established that the mesomorphism of 1,2,4-triazole derivatives is associated with the formation of supramolecules with a higher polarizability anisotropy. The calculation results confirmed the possibility of lateral hydrogen bonding which favors layered smectic packing.
Chemical Transformations of Chlorophyll a and Possible Areas for Application of Its Derivatives
Аннотация
Chemical transformations of chlorophyll a, aimed to develop photosensitizers for the antimicrobial and anticancer therapy, as well as for boron neutron capture therapy, have been considered. Research works on the development of purpurine 18 and its analogues have been presented; derivatives with intensive absorption in the near-infrared region of the spectrum, looking promising for photodynamic anticancer therapy, have been synthesized. A large series of works on the synthesis of N-hydroxy and N-amino cycloimides of chlorin p6 have been carried out. Carbohydrate derivatives of chlorin, containing the indicated fragments in various positions of the macrocycle, have been synthesized. The synthesis of chlorin conjugates with the closo-decaborate fragment and bis-dicarbollide of cobalt has been performed. The methods of 1,3-dipolar cycloaddition and the Sonogashira reaction have been used to obtain these conjugates. Chlorin-fullerene conjugates, including water-soluble derivatives, have been synthesized and their spectral and other physicochemical properties have been studied.