Russian Journal of Organic Chemistry最新文献

Oxidative cleavage of (+)-3-carene gave vicinal disubstituted dimethylcyclopropane α,ω-amido- and ketoesters, and intramolecular cyclization of the latter by the action of methanesulfonic acid afforded (4R)-4-ethenyl-5,5-dimethyltetrahydrofuran-2-one and 6,6-dimethyl-5-(2-oxopropyl)tetrahydro-2H-pyran-2-one.

This study aimed to synthesize and characterize a series of 2-amino-6-methyl-5-(morpholine-4-carbonyl)-4-(mono- and dihalophenyl)-4H-pyran-3-carbonitrile derivatives 4a–4e through a one-pot multicom­ponent reaction. The primary focus was to investigate their phase transition behavior and assess their potential for liquid crystalline applications, particularly in display and optoelectronic technologies. The synthesized derivatives were characterized using spectroscopic techniques to confirm their molecular structures. Their phase transition behaviors were analyzed using polarized optical microscopy (POM) to identify liquid crystalline properties, including nematic and isotropic phase transition temperatures. The results indicated that compounds 4d and 4e exhibited nematic behavior, transitioning at 171.8 and 185.6°C, respectively, while 4a, 4b, and 4c transitioned directly to the isotropic phase within the temperature range of 185.7–221.6°C, lacking liquid crystalline properties. The presence of mono- or dihalophenyl played a crucial role in promoting nematic behavior, enabling structured molecular arrangements in 4d and 4e. These findings highlight the significance of molecular design in developing liquid crystal materials for advanced applications such as displays and optoelec­tronics, while non-mesomorphic derivatives may be more suited for applications in organic semiconductors or pharmaceuticals. The study successfully identified two halogen-substituted 4H-pyran derivatives with nematic liquid crystalline behavior, emphasizing the importance of halogen substituents in tuning phase transition properties. These insights contribute to a broader understanding of functional material design and pave the way for further exploration of liquid crystal-based applications.

A molecular hybridization strategy was employed to synthesize 12 pyrazole hydrazide derivatives incorporating a thiazole fragment as potential antifungal agents. The newly synthesized compounds were systematically characterized using various techniques, including ¹H and ¹³C NMR, ESI-MS, and elemental analysis. Notably, compound 4f exhibited a high inhibition rate against Valsa mali, particularly in in vivo experiments, where it demonstrated significantly superior antifungal activity compared to the commercially available fungicide fluxapyroxad. Furthermore, molecular docking analysis provided a rational explanation for the differences in antifungal efficacy between compound 4f and fluxapyroxad.

A new efficient catalyst has been proposed for the Meinwald rearrangement of terminal epoxides with the formation of 1,3-dioxolane derivatives. Terminal epoxides have been converted in high yields into acetonyl derivatives in the presence of a catalytic amount of tetraethylammonium iodide. Anomalous condensation of 4-(3,6-dichloro-9H-carbazol-9-yl)-3-hydroxybutanenitrile with aldehydes and ketones in alkaline medium has been revealed. This condensation is accompanied by elimination of water and yields exclusively products with a Z-butadiene fragment.

Reactions of 1,1′-biadamantanes in nitric acid medium in the presence of nitrogen nucleophiles afforded a number of symmetrical difunctional derivatives. Reactions of 1,1′-biadamantane-3,3′-diols with carbon nucleophiles were carried out in sulfuric acid medium. A series of new tetra- and hexasubstituted functionalized 1,1′-biadamantane derivatives were synthesized in the system H₂SO₄–HNO₃.

N-(2,5-Dimethylphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine is the key intermediate product for the synthesis of imatinib and is the key structural feature which is likely to be responsible for its inhibitory effect against BCR-ABL kinase. In the present study, sixteen compounds were designed as possible alternatives to Imatinib to overcome the resistant cases. These compounds were synthesized by reactions of N-(2,5-dimethyl­phenyl)-4-(pyridin-3-yl)pyrimidin-2-amine with substituted benzoyl chlorides, chlorobenzenes, benzyl chlorides, and benzaldehydes under appropriate reaction condition. The new derivatives were characterized by spectral techniques such as FT-IR and NMR spectroscopy and mass spectrometry to confirm their structures. The novel imatinib analogues were then screened for their in vitro cytotoxicity against A549 and MCF7 cancer cell lines via MTT assay protocol. The compounds showed moderate antiproliferative activity at a concentration of 10 μM; among them, two derivatives exhibited antiproliferative activity at cell viability of 19.23±3.26 and 25.77±1.52 for A549 and 20.44±3.11 and 26.17±3.64 for MCF7.

New imidazole derivatives 2a–2c were synthesized and characterized by FT-IR and NMR spectroscopic methods. Density functional theory (DFT) method with 6-311++G(d,p) basis set was used for the theoretical study of compounds 2a–2c. To make it comparable with experimental data, the IR study was carried out in the gaseous state and NMR study was carried out in DMSO as a solvent. The obtained structural and spectral data confirmed the molecular structures of compounds 2a–2c. Gamma ray shielding parameters of compounds 2a–2c were examined with Monte Carlo-based Geant4/GATE, Phy-X/PSD, and XCOM simulations. The newly synthesized compounds were assessed for their antimicrobial properties against nine pathogenic microorganisms responsible for various diseases. The molecular docking simulations were conducted using the 3D structures of key bacterial proteins with compound 2a to examine the critical interactions responsible for its antibacterial activity, considering the results obtained for the bacterium E. faecalis.

A series of polyfluorinated triarylpyrazolines containing cationic piperazinium fragments in the fluorinated rings have been synthesized by substitution of para-fluorine atoms by 1-methylpiperazine and subsequent quaternization of the piperazine nitrogen atom. The relation between the structure of the obtained salts and their spectral characteristics has been studied, and photobleaching quantum yields in the presence of tetrabutylammonium butyl(triphenyl)borate have been measured.

Fe₃O₄@SiO₂Pr@4-hydroxy-3-methoxybenzaldehyde/bis(thioglycolic acid) nanoparticles were prepared and analyzed by FT-IR, VSM, TEM, EDX, and FE-SEM techniques. The synthesized nanoparticles were applied as an efficient and magnetically reusable nanocatalyst for the preparation of various thiazolidinone derivatives under solvent-free condition. The proposed protocol offers many benefits such as productivity, fast reaction, and convenience for work and recovery. The catalyst is reusable for 6 runs by decantation using an efficient magnet without notable loss in activity.