The importance of the research lies in the fact that on the basis of extreme environmental conditions, the diversity of phytopathogenic fungal and bacterial strains increases in various aspects - morphology, virulence, resistance to various factors, including the action of chemical preparations, thus increasingly requiring the development of effective preparations against these phytopathogenic agents. The purpose of the research was to establish the antimicrobial effect of new vinyl-triazole derivatives (DVT) on some isolates of the Fusarium semitectum fungus and phytopathogenic bacteria under in vitro conditions. The objectives were to investigate the action of the new compounds on the mentioned phytopathogenic agents, which led to the identification of DVT: EPS-860, EPS-165, EPS-297, with complex antimicrobial activity, thus providing opportunities for their use in plant protection measures against the fungus F. semitectum and the bacteria Erwinia carotovora, Xanthomonas campestris.
This study explores the synthesis of lawsone-derived aminonaphthoquinones with potential anticancer activity via the one-pot Mannich reaction. A series of nine lawsone Mannich bases, five of them being novel, were obtained from 2-hydroxy-1,4-naphthoquinone, butylamine/benzylamine, and various benzaldehydes under mild conditions in ethanol at room temperature, with convenient isolation by precipitation. The synthesized compounds were characterized by melting point, elemental analysis, and FTIR spectroscopy. Their cytotoxicity toward the human malignant melanoma cell line A375 was evaluated using MTT and LDH endpoint assays. The compounds showed concentration-dependent biological effects, with increased mitochondrial activity at lower doses and loss of cell viability at higher concentrations. These results highlight the value of the Mannich reaction as a simple route to diverse lawsone-derived bioactive scaffolds, and support further investigation of lawsone Mannich bases.
This work is focused on the synthesis of 1,2,3-triazole derivatives based on the artemisinin scaffold, employed as a valuable structural motif in the design of biologically active compounds. The coppercatalyzed azide-alkyne cycloaddition reaction was investigated using carane and steroidal azides. It was demonstrated that the nature of the azide and the reaction conditions significantly influence the yield and course of the process, including secondary hydrolysis and rearrangement pathways. As a result, hybrid compounds incorporating both artemisinin and 1,2,3-triazole fragments were obtained. The structures of the products were confirmed by modern spectroscopic methods (IR, ¹H and ¹³C NMR, HSQC, HMBC, NOESY) and mass spectrometry.
"Click chemistry" has become a popular method for the rapid synthesis of pharmaceutical compounds, with azides and alkynes significantly affecting the reaction rate and regioselectivity in [3+2] cycloadditions. (+)-3-Carene derivatives with chiral centers were converted into azidoalcohols and subsequently into heterorganic compounds through [3+2] cycloaddition, with the effects of substituents and reaction conditions studied. Hybrid molecules containing 2-carene fragments and nitrogen-containing heterocycles were synthesized, achieving yields ranging from 45-74%. Cytotoxic activity was evaluated across multiple cell lines; compounds 8, 9, 14, and 15 were non-toxic, while compounds 3, 4, and heterocompounds 5-7, 10-14, and 16 showed moderate activity. Product 17 exhibited the highest cytotoxic activity, with IC₅₀ values below 10 μM across all cell lines.
The oxidative polycondensation method was used to synthesize an oligomer based on methaphenylenediamine and resorcinol, in an acidic medium, utilizing potassium persulfate as an oxidizing agent. The goal of this study was to obtain multifunctional materials with enhanced physicochemical features and electroactive qualities. FTIR, NMR, ESR spectroscopy, thermogravimetric analysis (TGA), and scanning electron microscopy (SEM) were used to characterize the synthesized materials. The formation of the polymer backbone and the addition of amine and phenolic groups were verified by FTIR and NMR data. Unpaired electrons were found by ESR analysis, suggesting electroactive behavior. While SEM images revealed a comparatively uniform morphology, TGA showed good thermal stability. The materials that were obtained show promise for use in electrochemical systems and sensors.
A p-phenylenediamine-catechol-based oligomer was synthesized via oxidative polycondensation in an acidic medium under ultrasonic irradiation, employing potassium persulfate as the oxidant to obtain an oligomeric material. The resulting material was characterized by Fourier-transform infrared (FT-IR) spectroscopy, ultraviolet-visible (UV-Vis) spectroscopy, thermogravimetric analysis (TGA), nuclear magnetic resonance (NMR) spectroscopy, scanning electron microscopy (SEM), X-ray diffraction, and electron spin resonance (ESR) spectroscopy. FT-IR and NMR analyses confirm that the reaction conditions (with and without surfactant, in presence of ethanol) significantly affect the composition of the resulting materials. It was established that, depending on the reaction conditions, the formation of a trimer composed of two para-phenylenediamine units and one catechol moiety, as well as the formation of poly-1,2-dihydroxybenzene, occurs in different ratios. No products of the individual polycondensation of p-phenylenediamine were detected. UV-Vis spectroscopy indicates wide-band-gap semiconducting behavior, with an optical band gap of approximately 4.7 eV estimated from the Tauc plot analysis. TGA shows the oligomer is stable up to similar to 270 degrees C. SEM revealed an irregular, predominantly flake-like fragmented surface morphology without well-defined individual particles. ESR confirmed unpaired electrons within the oligomer structure. Temperature-dependent conductivity measurements revealed an unusual conductivity trend, where conductivity slightly increased with decreasing temperature within the investigated range. At room temperature, the measured conductivity is 1.06 & times; 10(-7) S/cm.
The paper addresses the synthesis and evaluation of hydrophosphoranes derived from (+)-3-carene as chiral ligands in asymmetric catalysis. Through oxidative transformations and subsequent reactions, spiro-hydrophosphorane-type compounds were obtained and characterized by spectroscopic methods (IR, NMR). These compounds were employed in palladium-based catalytic systems for allylic sulfonylation and amination reactions. The results indicate a limited influence of complexation time on the yield of racemic products, while highlighting the occurrence of asymmetric induction (up to 37% ee) under optimal conditions. Furthermore, the nature of the amine and the solvent significantly affects conversion and selectivity. The study demonstrates the potential of hydrophosphoranes as efficient ligands in asymmetric catalysis, providing perspectives for the development of high-performance catalytic systems.
This paper describes a method for the synthesis of biologically active compounds based on 1(alkyl/aryl)-2-(1H-1,2,4-triazol-1-yl)ethanones with aromatic aldehydes under Knövenagel reaction conditions. The studies are based on the possibility of selectively using 1-(alkyl/aryl)-2- (1H-1,2,4-triazol1-yl)ethanone derivatives, a distinctive structural feature of which is the presence of an activated methylene group; when this group reacts with aldehydes, it yields N-vinyl-triazoles in which the nitrogen atom is bonded to an sp²-hybridized carbon atom of a substituted olefin. In reactions with salicylic aldehyde derivatives, these compounds form hemiketals in which the carbon atom of the carbonyl group becomes asymmetric. An evaluation of the "structure-bioactivity" relationship was conducted for a series of synthesized alkyl/aryl-substituted N-vinyl triazoles. The resulting compounds exhibit biological activity and show promise for application in medicine and agriculture as antimicrobial agents and plant growth regulators.
The importance of the research lies in the fact that against the background of extreme environmental conditions, the diversity of phytopathogenic fungal strains increases in various aspects - morphology, virulence, resistance to various factors, including the action of chemical preparations, thus increasingly demanding the development of effective preparations against phytopathogenic agents. The purpose of the research was to establish in vitro conditions the antifungal effect of new vinyl-triazole derivatives (DVT) against one of the most widespread fungi - Nigrospora maydis. The objectives were to establish the specifics of the effectiveness of the mentioned preparations depending on the structure and concentration. It was established that EPS-165, MF-EPS-297, MF-EPS-860 exhibit pronounced antifungal activity in the concentration range of 0.0025 ... 0.02%, thus there are opportunities for their use in plant protection measures against the fungus Nigrospora maydis.
Sixteen 3,4‐dihydropyrimidin‐2(1 H )‐ones and ‐thiones were synthesized and evaluated for antimicrobial activity against both resistant and nonresistant bacterial strains, as well as four fungal species. Antibacterial testing revealed MIC/MBC values ranging from 0.25 to 8.0 mg/mL, with compound 20 demonstrating the most potent activity (MIC: 0.42–2.0 mg/mL). Notably, compound 16 exhibited consistent efficacy against both resistant and nonresistant strains. Antifungal activity was assessed against Aspergillus fumigatus , Aspergillus niger , Penicillium funiculosum , and Candida albicans , with compound 20 again emerging as the most effective (MIC: 0.75–2.0 mg/mL). Compounds 16 and 25 also showed antibiofilm activity, with compound 16 inhibiting biofilm formation by 70.22%. Preliminary cytotoxicity screening against cancer cell lines indicated that several compounds exhibited moderate anticancer activity. ADMET (absorption, distribution, metabolism, excretion, and toxicity) analysis suggested favorable pharmacokinetic profiles, with no violations of Lipinski's Rule of Five. Molecular docking studies suggest that the antibacterial mechanism may involve inhibition of the MurB enzyme, while antifungal activity is likely mediated through inhibition of cytochrome P450 (CYP) enzymes.These findings underscore the potential of 3,4‐dihydropyrimidin‐2(1 H )‐(thi)ones as promising lead compounds for the development of novel antibacterial and antifungal agents.
This work was aimed at the synthesis of new eutectic mixtures based on 1-methyl-1H-imidazole. The structure of compounds was confirmed by physicochemical methods of analysis, IR-, 1 H and 13C NMR spectroscopy and elemental analysis data. The catalytic activity of the eutectic mixtures synthesized in the Biginelli reaction was studied. The possibility of the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones has been demonstrated, thereby initiating a new direction for the production of optically active organic substances, including the compound with significant practical applications Monastrol.
This work was aimed at the synthesis of new eutectic mixtures based on 1-methyl-1H-imidazole. The structure of compounds was confirmed by physicochemical methods of analysis, IR-, 1H and 13C NMR spectroscopy and elemental analysis data. The catalytic activity of the eutectic mixtures synthesized in the Biginelli reaction was studied. The possibility of the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones has been demonstrated, thereby initiating a new direction for the production of optically active organic substances, including the compound with significant practical applications Monastrol
In this work the peculiarities of the heterocyclization reaction of vinyltriazoles with the participation of hydrazine hydrate in ethanol and acetic acid are considered. Within the framework of this work it was found that the nature of the formed reaction products of the interaction of vinyltriazoles with hydrazine hydrate depends on the nature of the solvent. In boiling ethanol, 4,5-dihydro-1H-pyrazolinfunctionalized 1H-1,2,4-triazole is formed. Under acetic acid conditions, along with the formation of a pair of diastereomeric substances 4,5-dihydro-1H-pyrazoline series diastereomeric substances undergoing acylation, the formation of triazolium salt of acetic acid undergoes decomposition with cleavage of 1H-1,2,4-triazole fragment and formation of 3,5-disubstituted pyrazole. The structure of the obtained compounds was confirmed by spectral data and elemental analysis
A novel poly(1,4-diaminonaphthalene) was synthesized from the monomer 1,4-diaminonaphthalene at the nanoscale via an oxidative polymerization method. The reaction was conducted in an acidic (HCl) medium under an ultrasound homogenizer at 0 °C, while potassium persulfate was used as a radical initiator. This polymer has been characterized using various techniques, including FTIR, UV-Vis spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), NMR analysis, and electron paramagnetic resonance (EPR) methods. The nanopolymers were found to be thermally stable up to 200 °C. EPR data further substantiated the presence of unpaired electrons on the nitrogen atoms within the polymer backbone.
Royal jelly is a secretion of the hypopharyngeal and mandibular glands of young nurse bees, used to feed larvae in the first three days throughout the larval period. The research evaluated the impact of the biostimulator "Chloramicob" on royal jelly production. It was established that the optimal dose is 2.25 ml/L administered to nurse bees (1 L sugar syrup/day for three days). In the first stage, it increased the larval acceptance rate by 12.5-27.5%, the mass of the brood by 2.4-14.4% and the total royal jelly production by 25.45-40.04%. In the second stage, increases of 10.0-24.3% in the number of larvae raised, 1.49-1.79% in the diameter of the queen cells and 41.14-93.38% in total royal jelly production. In the third stage, there were increases of 1.12-1.32% in the diameter of the queen cells, 1.13-3.30% in their length and 4.82-27.82% in the total royal jelly production obtained compared to the control group. The conclusion highlights that the use of the biostimulator "Chloramicob" in the feeding of nurse bees leads to an increase in the number of larvae accepted by 7.27-16.36% and in the total royal jelly production by 21.11-48.06% compared to the control group.
Background: Fixed-dose combinations have advanced in many therapeutic areas, including otorhinolaryngology, where hearing disorders are increasingly prevalent. Objectives: The present study focuses on developing and evaluating a new capsule combining nicergoline (NIC), piracetam (PIR), and hawthorn extract (HE) for the management of sensorineural hearing loss. Methods: The first phase methodology comprised preformulation studies (DSC, FTIR, and PXRD) to assess compatibility among active substances and excipients. Subsequently, four formulations were prepared and tested for flowability, dissolution behavior in acidic and neutral media, and stability under oxidative, thermal, and photolytic stress. Quantification of the active substances and flavonoids was performed using validated spectrophotometric and HPLC-UV methods. Results: Among the tested variants, the F1 formulation (4.5 mg NIC, 200 mg PIR, 50 mg HE, 2.5 mg magnesium stearate, 2.5 mg sodium starch glycolate, and 240.5 mg monohydrate lactose per capsule) displayed optimal technological properties, superior dissolution in acidic media, and was further selected for evaluation. The antioxidant activity of the formulation was confirmed through the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, Trolox Equivalent Antioxidant Capacity (TEAC), and iron chelation tests, and was primarily attributed to the flavonoid content of the HE. Acute toxicity tests in mice and rats indicated a high safety margin (LD50 > 2500 mg/kg), while ototoxicity assessments showed no adverse effects on auditory function. Conclusions: The developed formulation displayed good stability, safety, and therapeutic potential, while the applied workflow could represent a model for the development of future fixed-dose combinations.
Due to the importance of dihydropyrimidines, several new methodologies have recently been developed for the synthesis of monastrol and its derivatives. The most useful and elegant method currently in use is the multicomponent Biginelli reaction. Catalysis plays a fundamental role in the Biginelli synthesis. Monastrol and oxymonastrol differ from each other by the replacement of the sulfur atom present in monastrol with an oxygen atom in oxymonastrol. The synthesis methods used in these studies are the Biginelli cyclization method. The methods for detecting the final substances are: melting point, thin-layer and column chromatography, spectral methods: NMR, IR. From the point of view of "green chemistry", the most waste-free and environmentally friendly, it is of interest to obtain ionic liquids containing various active groups, for example, cyanoethyl, carboxyl, and on their basis to obtain eutectic mixtures and study their catalytic properties in the synthesis of monastrol (Kappe 1860).
Objectives: identification of new compounds with antifungal activity for the phytopathogenic fungus Fusarium culmorum. Methods: the isolation of F. culmorum strains was carried out in aseptic conditions on PDA (Potatoes Dextrose Agar) medium, with the subsequent identification of the species based on macro- and microscopic characteristics. Vinyl-triazole derivatives (D.V.T): EPS-165, MZ-115, MZ-118, EPS-23 were supplemented to the nutrient medium PDA in concentrations of 0,02; 0,01; 0,005; 0,0025; 0,00125%, sterilized by autoclaving. To assess the inhibitory effect of the studied preparations, the method of recording the diameter of the growing colonies was used. Results: the inhibitory effect of the studied preparations was specific depending on the concentration and the strain of the fungus investigated. The preparation MZ-118 offers wider opportunities for use in plant protection measures against the fungus F. culmorum. The factorial analysis demonstrated that in the system F. culmorum x D.V.T. x concentration, the main source of variation in fungal growth is D.V.T concentration. (50.2 ... 64.4%), followed by the isolate factor (24.7 ... 38.9%), which denotes the differential resistance of F. culmorum isolates to the action of the compounds under study.
This work focuses on the preparation and characterization product of a double coupling of 2‐methylaniline (2‐MeAn) with 1,3‐benzenediol (1,3‐BD) under ultrasound, using potassium persulfate (K 2 S 2 O 8 ) as an oxidant. The structure, morphology, and properties of the nanocomposite were characterized by Fourier transform infrared spectroscopy (FTIR), UV–vis spectroscopy, thermogravimetric analysis (TGA), X‐ray diffraction (XRD), scanning electron microscopy (SEM), NMR ( 13 C‐NMR, 1 H‐NMR, DEPT, HSQC, HMBC) analysis, mass spectroscopy (MS), and electron spin resonance (ESR) spectroscopies. The FTIR and NMR analysis revealed the presence of amin (─NH) and hydroxyl (−OH) groups in the synthesized product. UV–vis spectroscopy analysis demonstrated various electronic transitions at π–π* and n–π* levels, indicating poly‐conjugated systems within the compound. TGA results indicated good thermal stability. The conductivity of nanocomposites was 4.6 × 10 −7 S/cm. SEM examination of the synthesized material revealed that its morphology mainly consisted of fibers and a diameter in the range of 100–400 nm. XRD analysis revealed that synthesized nanocomposites showed a semicrystalline pattern. Electron spin resonance data further validated the existence of unpaired electrons on the nitrogen atoms within the material. Thus, a compound was obtained that, despite its low‐molecular structure, forms nanosized aggregates, which exhibit properties such as electrical conductivity similar to known oligomers.
The aim of this study was to synthesize free of metals polymeric organic materials that possess electrical conductivity. The nanoscale poly-(1,4-diaminonaphthalene) was synthesized using the oxidative polymerization method. The reaction was carried out in a hydrochloric acid solution at 0C, with potassium persulfate used as the oxidizing agent. The polymers were characterized using various techniques, including FT-IR, UV-Vis, TGA, NMR, EPR and SEM. It was found that the polymerization of 1,4-diaminonaphthalene occurs through the formation of N-C and N=C. UV studies revealed differences in the polymer chain conformations and polaron states. The UV-Vis spectra showed strong absorption bands at 250 and 340 nm, associated with π→ π* and n→ π* transitions, respectively. Electron Paramagnetic Resonance detected the presence of radicals in the polymer chain and established their position on the nitrogen atom. The micro-morphology study of the polymer revealed an irregular porous structure with pore sizes less than 5 μm. Additionally, it was demonstrated that the nanopolymers are thermally stable up to 140C.