Russian Journal of Organic Chemistry最新文献

New azo pyrimidine and pyrazole derivatives containing a quinazolin-4(3H)-one moiety were synthesized, and their antioxidant and antimicrobial effects were studied. The target compounds were obtained starting from ethyl 2-[2-(4-methoxyphenyl)-4-oxo-3,4-dihydroquinazolin-3-yl]acetate which was reacted with p-phenylenediamine, followed by diazotization, coupling with acetylacetone, and condensation with urea, thiourea, and substituted hydrazines. The synthesized compounds were characterized by melting points, FT-IR and ¹H and ¹³C NMR spectra, and elemental analyses. Some of them showed high antioxidant activity compared to ascorbic acid as standard drug, while the others exhibited moderate to low activity. The title compounds were also evaluated for antimicrobial activity by the well diffusion method and were found to be effective against Gram-positive and Gram-negative bacteria such as Escherichia coli, Bacillus cereus, and Staphylo­coccus aureus, as well as against the fungi Candida albicans and Rhizopus microsporum, at a concentration of 80 µg/mL.

The three-component reaction of carbocyclic enamino ketones, CH acids, and electrophiles has been studied. Previously unknown 5,6,7,8-tetrahydroisoquinoline derivatives have been synthesized via nucleophilic vinylic substitution (S_NVin). The structures of some of the obtained compounds have been determined by X-ray analysis.

A new catalytic one-pot synthesis of N-substituted β-amido carbonyl compounds has been developed using bismuth nitrate as highly efficient, commercially available, recyclable, and reusable acid catalyst. The efficiency of the proposed protocol was demonstrated by 17 examples including various functionalized N-substituted β-amido carbonyl compounds. The reaction utilized easily available and cost-effective starting materials and proceeded at room temperature in a short period of time, followed by aqueous workup.

Chemoselective Baeyer–Villiger oxidation of R-(+)-camphor with Caroʼs acid afforded a mixture of 1,2- and 3,4-campholactones.

A series of novel thiazolinone derivatives have been synthesized and characterized, and their biological activities have been studied. The title compounds were synthesized by condensation of different aldehydes 11a–11e with thiosemicarbazide to give thiosemicarbazones 12a–12e, which were cyclized with ethyl bromoacetate in the presence of sodium acetate to afford new thiazolinone derivatives 13a–13e. The structure of all newly synthesized compounds was elucidated by elemental analysis and FT–IR and multinuclear NMR (¹H and ¹³C) spectroscopy. Newly synthesized compounds 13a–13e showed weak or no antimicrobial activity against bacterial strains Escherichia coli and Staphylococcus aureus and fungal strain Candida albicans. Furthermore, the ADME properties of compounds 13a–13e were examined, and derivatives 13a and 13b but not 13c–13e were found to conform to Lipinskiʼs and Veberʼs rules without violations. The promising compounds 13a and 13b were docked against EGFR and VEGFR-2 binding sites with reduced energy scores, higher fitting, and stability.

A facile synthesis of a new series of 8-fluoro-10-methyl-3,4-dihydrobenzo[b][1,6]naphthyridine-2(1H)-carboxamide hybrids in high yields has been developed via coupling reaction. The synthesized com­pounds were evaluated for their in vitro anticancer activity against a panel of four human tumor cell lines, viz., MCF-7 (breast cancer), A-549 (lung cancer), OVACR-3 (ovarian cancer) and HeLa (cervical cancer). Com­pounds 12a, 12c, 12e, 12h, and 12l demonstrated higher activity than that of cisplatin taken as positive control.

Various five-membered heterocyclic compounds and highly functionalized open intermediates were simply synthesized by reacting (Z)–N³-(2-amino-1,2-dicyanovinyl)formamidrazone with selected reagents containing electrophilic carbon. The synthesized compounds were tested for antimicrobial activity and were found to have moderate antimicrobial effects.

The structure and ¹H NMR chemical shifts of a new structural analogue of endogenous thyronamines, 4-[4-(2-aminoethoxy)benzyl]aniline, have been simulated in the framework of the density functional theory. The molecular geometry of the title compound has been optimized at the B3LYP level of theory using 6-31G(d,p), 6-31+G(d,p), and 6-311G(d,p) basis sets both for the isolated molecule and including solvent effect. The ¹H NMR chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline have been estimated on the basis of magnetic shielding constants calculated by the GIAO method. In the calculations of both optimal molecular geometry and magnetic shielding constants, nonspecific solvation with dimethyl sulfoxide and methanol was considered in terms of the polarizable continuum model (IEFPCM). Linear correlations have been found between the theoretical and experimental chemical shifts of 4-[4-(2-aminoethoxy)benzyl]aniline in methanol-d₄ and DMSO-d₆.

This paper presents a broad overview of our research, which aims to develop new and effective synthetic approaches to structurally diverse heterocyclic scaffolds. Using multicomponent reactions (MCR), a wide variety of analogues from various families of heterocyclic compounds with many medicinal uses have been synthesized. Due to their affordability, eco-friendliness, and systematic synthesis in terms of reaction time, number of steps, yield, workup procedure, atom economy, and mild conditions, multicomponent reactions (MCRs) play a crucial role in achieving a greener approach in synthetic chemistry. MCRs offer a productive synthetic approach for a range of extremely complex compounds when paired with the one-pot process. The synthesis of highly functionalized molecules in a single pot to quickly generate libraries of biologically interesting compounds and find fresh leads as possible therapeutic agents is one of the distinctive features of MCRs. The current study covers the latest advancements and innovations of MCRs in the entire synthesis of nitrogen-, sulfur-, and oxygen-containing heterocyclic compounds.

A series of 3-aryl-8-nitro[1,2,4]triazolo[3,4-b][1,3,4]benzothiadiazepines have been synthesized by refluxing 4-amino-5-aryl-1,2,4-triazole-3-thiols and 5-nitro-2-chlorobenzaldeyde in methanol in the presence of glacial acetic acid as catalyst. The structure of the synthesized compounds was confirmed by spectral data, and their fungicidal activity against four fungal strains (Aspergillus niger, Helminthosporium oryzae, Rhizoctonia solani, and Penicillium citrinum) was evaluated. The drug likeness analysis and molecular docking were performed using Swiss ADME, Chimera, and AutoDock Vina tools.