Russian Journal of General Chemistry最新文献

A library of fifteen triazolyl nucleosides was synthesized by regioselective [3+2] cycloaddition reaction between azido nucleoside and various chalcones under thermal condition in the presence of catalyst tetrabutyl ammonium hydrogen sulfate. All synthesized compounds were evaluated antifungal activity against two phytopathogenic fungi Sclerotium rolfsii and Rhizoctonia solani. Most of the compounds demonstrated good to moderate activity against fungi.

The reaction of ethyl 3-aryl-2-cyanoacrylates (arylmethylene cyanoacetates) with N¹,N³-disubstituted malonamides in the presence of Et₃N under mild conditions (absolute EtOH, 25°C) produces new stable Michael adducts, ethyl 3-aryl-2-cyano-5-oxo-5-(N-R-amino)-4-(N-R-carbamoyl)pentanoates, in 57–95% yields. The structure of the obtained compounds was confirmed by IR, ¹H, ¹³C NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography. The stereochemical features of the obtained Michael adducts have been studied. Calculations using the semi-empirical GFN2-xTB method showed that the cyclization of the obtained adducts is a thermodynamically favorable process but has a high energy barrier (~206 kJ/mol) and cannot occur under the reaction conditions. The antibacterial activity of a series of the obtained Michael adducts was studied.

Phthalimides, a significant group of biologically active nitrogen-containing heterocycles, are widely present in pharmaceuticals, natural compounds, agrochemicals, polymers, and dyes. Additionally, they play a vital role as key intermediates in various organic transformations. A novel, straightforward, and practical one-pot synthetic approach has been developed for the preparation of phthalimide derivatives via a condensation reaction between aryl iodides and anilines, employing zinc acetate as a catalyst and DBU as a base in 1,4-dioxane as the solvent. This one-pot protocol provides these valuable desired compounds under mild conditions with excellent efficiency by using simple available starting materials. All the synthesized compounds screened for in vitro antibacterial activity against gram-positive and gram-negative strains.

A chiral organic fragment was linked to tetraphenylethylene (TPE) to produce (4S)-5,5-dimethyl-2-[4-(1,2,2-trityl)phenyl]thiazolidine-4-carboxylic acid (TPCA). The absolute conformation of TPCA was confirmed by Flack parameter to definite the atomic positions. Based on the peripheral four benzene rings of the TPE, the in situ temperature-dependent crystal structure of TPCA was established to demonstrate the conformational change of TPCA in the temperature range from 165 to 298 K, further to investigate the physical mechanism of molecular motions for AIE phenomenon. The isotropic parameters of the individual benzene rings can further confirm the unequal vibrations of the molecule caused by the crystal anisotropy.

The synthesis of novel α-aminophosphonate derivatives via Kabachnik–Fields reaction in the presence of triethylammonium acetate (TEAA) as medium was described. The title compounds were obtained with good yields in short reaction time. All synthesized compounds were tested for their in vitro antibacterial and antifungal activities and the results revealed that they exhibited high activity against gram-positive bacteria. In addition, to rationalize the observed biological data, computer-aided-molecular design has been used to describe the structure–activity relationship study (SAR) based on DFT calculation, molecular docking, and ADME properties. A good correlation was found between the theoretical investigations and experimental data. Altogether, these results suggest that the reported α-aminophosphonates are potential antimicrobial agents.

A broad approach for the synthesis of fused [1,2,3]triazolo[1′,5′:2,3]isothiazolo[4,5-d]pyrimidines from 2-chloropyrimidine-5-sulfonyl chloride, NaN₃, and several iodoalkynes was established via microwave-assisted one-pot Cu-catalyzed cycloaddition followed by C–C bong coupling reaction under PEG-400 medium. In vitro antibacterial efficacy of newly synthesized compounds against three Gram-positive bacterial strains such as Bacillus subtilis, Staphylococcus aureus, and Staphylococcus epidermidis. Two compounds were more active against two bacterial strains: B. subtilis and S. aureus. Furthermore, these two compounds have demonstrated significant biofilm action against S. aureus. We performed in silico investigations to evaluate the molecular interactions of more powerful drugs with TLR₄ proteins (PDB: 3FXI, 3VQ1, 3RG1). Our findings showed that the studied potent chemicals had higher binding energies to human, mouse, and bovine TLR4 proteins than dicloxacillin.

As our continuous endeavor for the design and synthesis of new pharmaceutical and bioactive materials, the present research describes the design and synthesis of a series of novel 1,2,4-triazoles, mono-(1,2,4-triazolo)-[3,4-b:4′,3′-d][1,3,4]-thiadiazoles and bis-(1,2,4-triazolo)-[3,4-b:4′,3′-d][1,3,4]thiadiazoles linked to C-furyl glycoside. The synthetic plan involved base catalyzed ring closure of thiosemicarbazide derivative of 3-carbethoxy-5-C-(l,4-anhydro-β-D-erythro-tetrofuranosyl)-2-methylfuran afforded the corresponding 1,2,4-triazol derivative. The synthesized compounds were assessed for their antimicrobial activity against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans. The compounds show high antimicrobial activity. The results obtained in antitumor tests showed that all compounds possess the highly significant effect against MCF7 and this is might be due to the presence of fused heterocyclic ring systems in addition to C-furyl glycoside moiety.

A series of dyes containing a thiobarbiturate fragment were synthesized via a standard azo coupling reaction, and their reactions with dimethyl(chloroethynyl)phosphonate were investigated. It was found that the phosphorylation reaction proceeds chemo- and regioselectively, leading to the formation of a thiazole ring.

The structure and composition of the calcium complex with meconic acid (5-hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid), calcium meconate, were studied. Elemental analysis and X-ray diffraction analysis determined the composition of the complex compound [Ca(H₂Mec)₂(H₂O)₄]·4H₂O. The compound crystallizes in the monoclinic space group P2₁/n as an octahydrate, with four water molecules in the first coordination sphere of the calcium cation and four additional water molecules forming the outer coordination sphere through hydrogen bonds. The formation of coordination bonds between the meconic acid residue and the calcium cation in the complex was also confirmed by indirect methods (NMR and IR spectroscopy). Quantum chemical calculations were used to correlate the experimental and calculated vibrational frequencies in the IR spectrum of calcium meconate.

A method for the direct introduction of 2-(R-phenacyl)methyl-5-aryl(heteryl)tetrazole fragments into the molecule of 2-R-6-nitro-1,2,4-triazolo[1,5-a]pyrimidines via a nucleophilic addition reaction has been developed. The antimicrobial activity of some synthesized compounds was evaluated against the reference strain Neisseria gonorrhoeae ATCC 49226/NCTC 12700 and museum strains of dermatophyte and yeast-like fungi.