Russian Journal of General Chemistry最新文献

A series of novel 3,4,7- or 3,4,8-trisubstituted-3a,4-dihydro[1,2,3]triazolo[1,5-a] quinazolin-5(3H)-one analogues was synthesized and characterized by using HRMS, ¹H NMR and ¹³C NMR spectral data. All the compounds were tested for their in vitro antitubercular activity by using the Microplate Alamar Blue Assay technique, the minimum inhibitory concentration values of the most effective inhibitors were determined for Mycobacterium tuberculosis H37Rv and H37Ra strains by using rifampicin, isoniazid and ethambutol as reference standards. Among all synthesized compounds 7-chloro-3-(3-chloropyridin-4-yl)-4-methyl[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one, 7-bromo-8-chloro-4-(4-fluorophenyl)-3-(3-methylpyridin-4-yl)[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one and 7-bromo-4-(4-methoxyphenyl)-3-(3-methylpyridin-4-yl)-[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one exhibit excellent in vitro antitubercular activity when compared to the reference standards. Further 7-bromo-8-chloro-4-(4-fluorophenyl)-3-(3-methylpyridin-4-yl)[1,2,3]triazolo[1,5-a]quinazolin-5(4H)-one was evaluated for in vivo antitubercular activity after post treatment in female BALB/c mice by determination of log10 colony formation unit in lungs and spleen. Therefore, this compound could serve as the lead molecule for further development as antitubercular agent.

A series of 5-methyl-1,2,4-triazol-3-ones containing salicyl or isatin moieties were synthesized by using conventional and microwave heating techniques. In microwave heating, the compounds were synthesized by using both a monomod microwave reactor and domestic type microwave oven and their results were compared. The synthesized compounds were evaluated for their urease inhibitory activities. Among the synthesized compounds two isatin containing 1,2,4-triazol-3-one derivatives (IC₅₀ = 0.5230±0.0318 and 0.4860±0.0317 µM) showed higher activities than salicyl containing derivatives (IC₅₀ = 0.5451±0.0315 and 0.7181±0.0345 µM), while standard thiourea showed IC₅₀= 0.5027±0.0293 µM activity.

Rhodiola carbon dots (R-CDs) were prepared by simple and economical one-pot hydrothermal method using Rhodiola as raw materials. The morphology and surface functional groups were analyzed by TEM, FT-IR, and XPS. It was discovered that R-CDs had COC, C=O and OH functional groups linked to the surface and had a common particle dimension of 2.56 nm. The prepared difunctional R-CDs showed high water-solubility and favorable photostability. Additionally, it was unexpectedly discovered that R-CDs confirmed great antibacterial motion in opposition to both E. coli and S. aureus, with a MIC of 0.7 mg/mL. Consequently, this study provides a new, green, economical carbon dot with the potential application as potent antibacterial.

In this study, we report the synthesis and characterization using various spectroscopic techniques of a series of six new furan-based Schiff base derivatives as potential antitubercular agents. The strategic incorporation of the furan scaffold and nitro group, both known for their diverse biological activities, provided a strong rationale for their evaluation against tuberculosis. Molecular docking simulations were employed to assess the binding affinities of these compounds towards enoyl-acyl carrier protein reductase (InhA), a validated and essential target in M. tuberculosis. Remarkably, all synthesized compounds exhibited superior binding scores (–6.074 to –9.939 kcal/mol), compared to the clinically used antitubercular drug isoniazid (–4.585 kcal/mol), indicating their potential as potent InhA inhibitors. Furthermore, in silico absorption, distribution, metabolism, and excretion (ADME) predictions were performed to evaluate the drug-likeness of these compounds. The findings highlight the balanced combination of potent target binding and drug-like characteristics achieved by these furan-based Schiff base hybrids.

Herein, the constructing synthon pyrazolyl-pyrimidine derivatives were synthesized and utilized for building a wide variety of 1,2,3-triazole and tetrazole compounds that can be used as antimicrobial and antitubercular medications. The structures of all synthesized compounds were characterized using different spectroscopic techniques (¹H, ¹³C NMR, IR and MS). The novel o,p-dihydroxyphenyl and isopropyl substituted tetrazoles have a remarkable antimicrobial activity against K. pneumoniae (MICs = 4.93±0.02, 4.13±0.01 µg/mL) and S. aureus (MICs = 7.72±0.02, 17.34±0.01 µg/mL). Antifungal activity of pyrazolyl-pyrimidine containing with p-hydroxybenzyl, o-hydroxy, and m-nitrophenyltriazoles displayed potent antifungal activity against A. niger, and its MIC was found to be, 5.45±0.02, 4.12±0.03, and 6.31±0.01 µg/mL. All the prepared tetrazoles exposed excellent antitubercular activity comparison with the standard drug against H₃₇RV strain. From docking investigations, the p-hydroxybenzyl-linked triazole revealed the strongest H-bonds among the residues Ile¹⁴(A), Arg⁴⁵(A), Gln⁶⁸(A), Gln⁹⁸(A) × 2, Thr⁴⁶(A), and Gly⁹⁶(A) against 1DF7 protein. Finally, the in silico pharmacokinetic profile of all the derivatives was estimated using SwissADME and some of the compounds have Lipinski rule of five without deviation.

Radical copolymerization of coumarin with N-vinylamides (N-vinylpyrrolidone, N-vinylformamide, and N-methyl-N-vinylacetamide) initiated by 2,2′-azobisisobutyronitrile in bulk at 65°C has been studied. The comonomer reactivity ratios for the monomer pairs N-vinylformamide/coumarin (r₁ = 0.22±0.03, r₂ = 0) and N-methyl-N-vinylacetamide/coumarin (r₁ = 0.08±0.01, r₂ = 0) have been determined. Water-soluble copolymers of N-vinylamides with salts of oxycinnamic acid have been synthesized via alkaline hydrolysis of the obtained coumarin copolymers.

A new method was developed for the synthesis of ethyl 3,6-diamino-4-aryl-5-cyanothieno[2,3-b]pyridine-2-carboxylates by the reaction of 4-aryl-2-amino-6-chloropyridine-3,5-dicarbonitriles with ethyl 2-mercaptoacetate. The synthesized compounds exhibit fluorescence both in solution and in the solid state. The emission maxima in benzene solution depend on the substituent and are in the range of 503–531 nm or from 498 to 541 nm in the solid state. For photoluminescence of ethyl 3,6-diamino-4-aryl-5-cyanothieno[2,3-b]pyridine-2-carboxylates, large Stokes shifts were observed: from 214 nm (13106 cm^–1) in chloroform to 251 nm (14433 cm^–1) in methanol.

This study explores the potential of paracetamin, an amine derivative of paracetamol, pronounced for its versatility as an intermediate for dye synthesis and biological application in addressing bacterial resistance. Here, a new series of halogenated triazene derivatives obtained through N-coupling reactions of paracetamin with halogenated aniline derivatives at ortho, meta, and para positions with a moderate yield of 19–72% were discussed. Antibacterial activity of these compounds evaluated against Staphylococcus aureus and Escherichia coli via Kirby–Bauer disc diffusion method observed that four of the compounds bearing fluoro-, chloro-, and bromo-substituents at meta as well as para-bromo substituted triazene displayed a great inhibition zone of 9–12 mm against both strains with ampicillin as its positive control. The structure–activity relationship through molecular docking analyses on CrtM and DNA gyrase enzymes revealed the binding scores of –7.1 to –8.3 and –8.3 to –8.6 kcal/mol respectively, highlighting the significant contribution of hydrogen bonding, hydrophobic and van der Waals interactions towards the binding affinity. Furthermore, the drug-likeness potential of the compounds was assessed through in silico ADMET and Lipinski’s rule of five where all compounds adhere and screened to have great pharmacokinetics properties, and low toxicity of 0.360–0.682 for particularly bromo substituted triazene derivatives outlining their potential drug bioavailability.

An eco-efficient and economic method was proposed for the synthesis of different chromenoquinoline-10,12(6H)-dione derivatives via mortar-pestle grinding. This synthetic approach uses a mixture of substituted arylaldehyde, cyclohexane-1,3-dione and 2-amino-4H-chromen-4-one in the presence of environmentally friendly [Et₃NH][HSO₄]. This approach encompasses a one-pot, three-component synthesis process that employs mortar-pestle grinding. It has several benefits, such as being cost-effective, easy to handle, and short reaction time (30 min). The reaction can be carried out at ambient temperature, and the purification process is short and simple, resulting in excellent yield (70–93%). ¹H, ¹³C NMR, FT-IR, MS analytical data were used for identification of synthesized derivatives. Furthermore, the method is environmentally friendly since it eliminates toxic solvents, column chromatography, and metal catalysts. The constructed 3,5-dichloro and 4-fluoro substituted chromenoquinoline-10,12(6H)-diones showed a good result against the chosen protein.

A new approach to the synthesis of 2-amino-4-aroyl-6-halopyridine-3,5-dicarbonitriles using commercially available saturated solutions of hydrogen halides is proposed. The synthesized compounds demonstrated binding properties towards mercury(II) ions, which is manifested in fluorescence quenching. The limit of mercury(II) detection with a leading compound falls in the nanomolar range, which is comparable to the known reagents based on small molecule compounds.