Russian Journal of Organic Chemistry最新文献

A novel electrochemical oxidation method utilizing potassium nitrate as a redox mediator is developed for the efficient oxidation of benzyl alcohols. In the two-phase electrolysis, the aqueous phase consisted of a 0.5% KNO₃ solution with a stoichiometric amount of sulfuric acid, while the organic phase comprised benzyl alcohols dissolved in chloroform. The electrolysis was carried out at ambient temperature employing an undivided cell with platinum electrodes to afford the corresponding aldehydes and ketones in high yields with >99% selectivity. The role of potassium nitrate in facilitating electron transfer and enhancing oxidation is elucidated. This approach offers a promising alternative for the oxidation of benzyl alcohols.

The reactions of tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile and 4,11-dimethyl-2,13-bis(4-methylphenyl)tribenzo[b,e,g][1,4]dioxocine-7,8-dicarbonitrile with sodium methoxide in methanol, followed by treatment with aqueous HCl, gave 11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindole-11,13(12H)-dione and 1,8-dimethyl-3,6-bis(4-methylphenyl)-11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindole-11,13(12H)-dione, respectively. Their condensation with 2-methylquinoline and subsequent treatment with boron trifluoride–diethyl ether complex in the presence of triethylamine afforded 12-(difluoroboranyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11H-dibenzo[5,6:7,8][1,4]dioxocino[2,3-f]isoindol-11-one and 12-(difluoro­boranyl)-1,8-dimethyl-3,6-bis(4-methylphenyl)-13-(quinolin-2-ylmethylidene)-12,13-dihydro-11H-diben­zo­[5,6:7,8][1,4]dioxocino[2,3-f]isoindol-11-one, respectively. The structure of the synthesized compounds was confirmed by elemental analyses and IR, NMR, and mass spectra. The complexes displayed high luminescence quantum yields (up to 0.65) while small Stokes shifts (up to 15 nm). Bands in the electronic absorption spectra of the complexes were assigned to particular electronic transitions on the basis of DFT and TDDFT calculations.

The synthesis of benzofuranyl coumarins from 4-(bromomethyl)coumarin and 2-hydroxy-4-methoxybenzophenone in dry acetone and in the presence of anhydrous K₂CO₃ in good yield is reported. Single-crystal X-ray structure determination confirmed the molecular structure of 4-(6-methoxy-3-phenyl­benzofuran-2-yl)-7-methyl-2H-chromen-2-one (4a). Protein denaturation inhibition and membrane stabilization assays were used to evaluate the in vitro anti-inflammatory activity of the synthesized compounds. 4-[(2-Ben­zoyl-5-methoxyphenoxy)methyl]-6-ethyl-2H-chromen-2-one (3b) showed the highest protein denaturation inhibition of 77.83±0.47% at a concentration of 100 μg/mL. 4-[(2-Benzoyl-5-methoxyphenoxy)methyl]-6-(propan-2-yl)-2H-chromen-2-one (3c) showed the strongest hemolysis inhibition by 90.43±0.42%. Molecular docking was performed with proteins involved in the inflammatory pathway. In addition, in silico studies were carried out to assess the ADMET profile of the synthesized benzofuranyl coumarins.

A series of fluorinated pyrazoles was synthesized in a straightforward manner without the use of hazardous catalysts, toxic solvents, or extreme reaction conditions, yielding high product efficiency. Fluorinated aldehyde and piperonal underwent a condensation reaction to form a chalcone intermediate, which was subsequently cyclized with hydrazine hydrate to yield the corresponding pyrazole derivatives. The structures of the synthesized compounds were confirmed using IR, ¹H NMR, and mass spectrometry. These compounds were then evaluated for their antibacterial and antitubercular activity. Molecular docking studies revealed high binding affinity scores across the entire series.

A two-step procedure has been proposed for the synthesis of Grieco lactone and its enantiomer from diastereomerically pure 2,2-dichloro-2-[(1R,5S)- and 2,2-dichloro-2-[(1S,5R)-5-hydroxycyclopent-2-en-1-yl]-N-[(1R)-1-phenylethyl]acetamides in an overall yield of 77%.

Tuberculosis (TB) caused by Mycobacterium tuberculosis (Mtb) continues to pose a major global health challenge, resulting in millions of infections and deaths annually. The treatment of TB is complicated by prolonged therapy, drug toxicity, reduced efficacy, and its frequent association with HIV co-infection. The emergence of drug-resistant Mtb strains has led to the failure of first- and second-line therapies, highlighting the urgent need for new antitubercular agents. In this context, hybrid drug design approaches have gained increasing attention. In the present study, a series of novel 3-(3-phenyl-1H-pyrazol-1-yl)-1H-indole derivatives were synthesized and structurally characterized. These compounds were evaluated in vitro against three Mtb strains, including H37Rv. Furthermore, molecular docking studies were conducted to assess the binding interactions and affinities of the synthesized ligands with the enoyl–acyl carrier protein reductase (InhA) enzyme (PDB ID: 4TZK), a validated target for antitubercular therapy.

This study focused on the design, synthesis, and evaluation of novel quinazoline Schiff bases as potent inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK), with an emphasis on their antiproliferative effect against A549 lung cancer cell line. The compounds were computationally designed and synthesized, and molecular docking studies were conducted to examine their interactions within the EGFR-TK binding pocket. Molecular dynamics simulations were performed to assess the stability and conformational behavior of the hybrids, while Density Functional Theory (DFT) calculations were employed to validate their optimized geometries. Among the synthesized compounds, three analogues demonstrated significant inhibitory activity. In particular, compound 6b featuring a p-hydroxyphenyl group showed an IC₅₀ of 1.44±1.07 µg/mL, while compound 6f with a 4-fluorophenyl moiety showed an IC₅₀ of 1.58±1.25 µg/mL. and compound 6h with a 3,4-dimethoxyphenyl moiety exhibited an IC₅₀ of 1.7±1.32 µg/mL. Erlotinib used as reference drug displayed an IC₅₀ of 7.32±0.52 µg/mL. Molecular modeling identified key structural features contributing to the observed activities. This comprehensive study highlights the potential of quinazoline Schiff bases as promising EGFR-TK inhibitors, offering insights into their structural optimization and interactions for cancer therapy.

7-(Ethoxymethyl)-4′,4′-dimethyl-2-(3-nitrophenyl)-2′,6′,8-trioxo-5,7-diazaspiro[bicyclo[3.3.1]nonane-3,1′-cyclohexane]-1-carbonitrile has been synthesized by the reaction of 2-amino-7,7-dimethyl-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile with aqueous formaldehyde in ethanol under reflux, and its molecular and crystal structures have been determined by spectral methods and X-ray analysis.

Herein we report a convenient and green synthesis of a new class of phosphonopyrans—2-amino-3-cyano-6-phosphonoethyl-4H-pyrans—through the K₂CO₃-catalyzed reaction of malononitrile with γ-keto-δ-alkenylphosphine oxides. The reaction proceeds under operationally simple and mild conditions, employs a low-cost and an environmentally benign catalyst and ethanol as a green solvent.

6-(2-Bromoethyl)-6H-indolo[2,3-b]quinoxaline was synthesized and reacted with arylamines to obtain N-(2-[6H-indolo[2,3-b]quinoxalin-6-yl)ethyl]arylamines and N,N-disubstituted 4-methylaniline. Previosly unknown 6-vinyl- and 6-(2-azidoethyl) derivatives of 6-(2-bromoethyl)-6H-indolo[2,3-b]quinoxaline and indolo[2,3-b]quinoxaline–pyrimidine and 1,2-bis(6H-indolo[2,3-b]quinoxalin-6-yl)ethane hybrids were also synthesized. Molecular docking studies of the synthesized indolo[2,3-b]quinoxaline derivatives against 4 different receptors indicated high predicted activity for the indoloquinoxaline–pyrimidine conjugate.