503 results on '"Azomethines"'
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2. Zinc Complexes of Fluorosubstituted N -[2-(Phenyliminomethyl)phenyl]-4-methylbenzenesulfamides: Synthesis, Structure, Luminescent Properties, and Biological Activity.
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Burlov, Anatolii S., Vlasenko, Valery G., Milutka, Maxim S., Koshchienko, Yurii V., Lazarenko, Vladimir A., Trigub, Alexander L., Kolodina, Alexandra A., Zubenko, Alexander A., Braga, Elena V., Gusev, Alexey N., and Linert, Wolfgang more...
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ZINC compounds , *CHLORINE , *ZINC compounds synthesis , *CRYSTAL structure , *METAL complexes , *LUMINESCENCE , *ANTIBACTERIAL agents - Abstract
Mono-, di-, and trifluorophenyl substituted in different positions of amine fragments bis [2-[[(E)-((fluorophenyl)iminomethyl]-N-(p-tolylsulfonyl)anilino]zinc(II) complexes were synthesized. Their crystal structure, photo- and electroluminescent properties, and protistocidal, fungistatic, and antibacterial activities were studied. It has been shown that the introduction of fluorine atoms and an increase in their number in the ligand structure of the resulting metal complexes promote the luminescence quantum yields and values of performance and brightness in EL cells compared to their previously studied chlorine-substituted analogs. [ABSTRACT FROM AUTHOR] more...
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- 2024
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Catalog
3. Azomethine‐Containing Pyrrolo[3,2‐b]pyrrole Copolymers for Simple and Degradable Conjugated Polymers.
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Bartlett, Kimberley A., Charland‐Martin, Ariane, Lawton, Jonathan, Tomlinson, Aimée L., and Collier, Graham S.
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CONJUGATED polymers , *COPOLYMERS , *POLYMER degradation , *POLYMER solutions , *PYRROLES , *ACID catalysts - Abstract
Conjugated polymers have received significant attention as potentially lightweight and highly tailorable alternatives to inorganic semiconductors, but their synthesis is often complex, produces toxic byproducts, and they are not typically designed to be degradable or recyclable. These drawbacks necessitate dedicated efforts to discover materials with design motifs that enable targeted and efficient degradation of conjugated polymers. In this vein, the synthetic simplicity of 1,4‐dihydropyrrolo[3,2‐b]pyrroles (DHPPs) is exploited to access azomethine‐containing copolymers via a benign acid‐catalyzed polycondensation protocol. Polymerizations involve reacting a dialdehyde‐functionalized dihydropyrrolopyrrole with p‐phenylenediamine as the comonomer using p‐toluenesulfonic acid as a catalyst. The inherent dynamic equilibrium of the azomethine bonds subsequently enabled the degradation of the polymers in solution in the presence of acid. Degradation of the polymers is monitored via NMR, UV‐vis absorbance, and fluorescence spectroscopies, and the polymers are shown to be fully degradable. Notably, while absorbance measurements reveal a continued shift to higher energies with extended exposure to acid, fluorescence measurements show a substantial increase in the fluorescence response upon degradation. Results from this study encourage the continued development of environmentally‐conscious polymerizations to attain polymeric materials with useful properties while simultaneously creating polymers with structural handles for end‐of‐life management or/and recyclability. [ABSTRACT FROM AUTHOR] more...
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- 2024
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4. In silico and In vitro Study of Antithyrosinase Activity of New Schiff Bases — Azomethine Derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
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A. S. Chiriapkin, I. P. Kodonidi, and D. I. Pozdnyakov
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tyrosinase ,azomethines ,molecular docking ,anti-tyrosinase activity ,2-amino-4 ,7-tetrahydro-1-benzothiophene-3-carboxamide ,Science ,Medicine ,History of scholarship and learning. The humanities ,AZ20-999 - Abstract
Introduction. Skin hyperpigmentation is an important problem of dermatocosmetology. The resulting pigment spots on the skin of a person, especially in open areas of the body, affect their psychoemotional state and social adaptation, and in some cases trigger dermatological diseases. The aim of the study is to search for new effective and safe compounds with anti-tyrosinase activity. Materials and methods. Seven new previously synthesized azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide are the objects of research. To study in silico the molecular mechanisms of tyrozinase inhibition by the compounds under study, the method of molecular annealing was used. The inhibitory activity of tyrosinase was determined according to the method by Mapunya et al. (2012). Results. During the computational experiment, we determined amino acid residues of the active tyrosinase site, with which azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide interact. In vitro evaluation of the anti-tyrosinase activity of the studied compounds indicated that almost all the analyzed substances were inferior to the referents in terms of the strength of biological action, except for compound 1, which was superior in activity to kojic and lactic acids. Based on the LD50 value of compound 1, it was assigned to the 5th class of toxicity according to the GHS classification. Conclusion. In the course of the conducted research, it was found that structure 1 surpasses kojic and lactic acids in the severity of its pharmacological activity. We consider it appropriate to further pharmacological studies of this substance. more...
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- 2023
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5. Fe spin states and redox processes in Schiff base type complexes.
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Várhelyi Jr., Cs., Szőke, Á., Sziráki, L., Tomoaia-Cotișel, M., Homonnay, Z., Szalay, R., Simon-Várhelyi, M., Mereu, R.-A., Pokol, Gy., Szilágyi, I.-M., Papp, J., Mihály, J., and Kuzmann, E.
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INFRARED spectroscopy , *ATOMIC force microscopy , *OXIDATION-reduction reaction , *THERMAL analysis , *CYCLIC voltammetry , *ETHANOL , *MOSSBAUER spectroscopy , *PHENYLENEDIAMINES , *SCHIFF bases - Abstract
Novel iron(II) Schiff base type complexes of [Fe(4-benzyl-2-hydroxy-propiophenone)2(o-phenylenediamine)], [Fe(ninhydrin)2(ethylenediamine)], [Fe(ninhydrin)2(1,2-propylenediamine)], [Fe(2,4,6-trihydroxy-benzyl-4-methoxyphenyl-ketone)2(ethylenediamine)] and [Fe(ninhydrin)2(1,3-propylenediamine)] have been prepared by reaction of the components dissolved in ethanol at refluxing temperature in inert atmosphere, and were characterized by mass spectrometry (MS), infrared spectrometry (IR), thermal analysis, atomic force microscopy (AFM), 57Fe Mössbauer spectroscopy, cyclic voltammetry and biological activity tests. Mössbauer spectroscopy revealed the dominant occurrence of high spin FeII besides minor or no low spin FeII in the complexes, and minor FeIII impurity phase. The cyclic voltammograms indicated peaks due to redox processes in certain complexes. In these cases the occurrence of low spin FeII was also observed. Low biological activity was experienced for some compounds. The thermal decomposition process of all complexes was performed by TG–DTG–DTA analysis in air atmosphere aiming to understand the mechanism of the mass change with increasing temperature. The importance of the current research is to find correlation between the Fe spin states, redox processes and biological activity. [ABSTRACT FROM AUTHOR] more...
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- 2023
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6. New Schiff Base Derivatives: Preparation, Antioxidant Activity, and DFT Investigation of Structural Properties.
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Adjeroud, Y., Bouzitouna, A., Bakchiche, B., Nacereddine, A. Khorief, Bendjeffal, H., and Liacha, M.
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SCHIFF base derivatives , *FRONTIER orbitals , *NUCLEOPHILIC reactions , *CHEMICAL synthesis , *CONDENSATION reactions , *ETHANOL , *AROMATIC aldehydes - Abstract
A series of novel Schiff bases was synthesized with good yields from 2(3H)-benzoxazolone using the condensation reaction between 6-amino-2(3H)-benzoxazolones and different substituted aromatic aldehydes under refluxing ethanol in the presence of acetic acid as a catalyst. The antioxidant activity of the obtained compounds was evaluated, the control using butylated hydroxytoluene (BHT) indicates that the four synthesized compounds showed excellent free radical scavenging activity. Complementary DFT study of some spectroscopic and electronic properties of a selected product's structures was also performed within the B3LYP/6-311++G(d,p) level of theory. The molecular electrostatic potential analysis indicates that the studied compounds may be used as good reagents for electrophilic or nucleophilic attacks. Frontier molecular orbitals (FMO) analysis shows also that these structures are characterized by a low gap energy accounting for high reactivity. The reactivity indices indicate that these compounds are suitable starting materials for performing several nucleophilic or electrophilic reactions. [ABSTRACT FROM AUTHOR] more...
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- 2023
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7. Visible light-promoted, catalyst-free synthesis of isoniazid azomethines: In vitro antioxidant activity, molecular docking, ADME and toxicity prediction.
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Iqbal, Safia, Hussain, Mohd Kamil, Ansari, Roohi, Singh, Bhoomika, Farhanaz, Akbar, Insha, Zaheer, Mohammad Rehan, Khan, Mohammad Faheem, and Gupta, Anamika
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SUSTAINABLE chemistry , *SUSTAINABILITY , *HYDROGEN peroxide , *HORSERADISH peroxidase , *CHEMICAL synthesis - Abstract
• This study highlights a sustainable approach with promising therapeutic applications. • EDA-mediated VLCF synthesis offers an eco-friendly route to isoniazid azomethines. • Isoniazid azomethine 3e demonstrates superior antioxidant potential among analogues. • Molecular docking reveals strong binding affinity of 3e, suggesting effective inhibition. • In silico ADMET analysis confirms favorable safety and pharmacokinetic profiles. Green synthesis of biologically active molecules is essential for environmental sustainability, resource efficiency, reduced environmental impact, and compliance with regulations. It ensures a safer working environment, and fosters innovation in sustainable chemistry practices. In this context, we introduce an electron donor-acceptor (EDA)-mediated visible light-promoted, catalyst-free (VLCF) scalable synthesis of isoniazid azomethines. This synthesis encompasses the drug salizide and its analogues, which were subsequently evaluated for their antioxidant activities. Isoniazid azomethines 3e demonstrated superior activity compared to salizide and ascorbic acid, with an IC 50 of 0.078 mg/mL in the hydrogen peroxide antioxidant assay. Specifically, 3e exhibited greater antioxidant properties (79.02 %) than isoniazid azomethine 3b (75.82 %), isoniazid azomethine 3d (62.2 %), isoniazid azomethine 3c (59.86 %), and isoniazid azomethine 3a (54.62 %). In the superoxide dismutase antioxidant assay, 3e was also identified as the most active, with a SOD activity level of 650 U/mg of protein, surpassing other compounds (3a-d) with SOD activity levels of 330, 560, 350, and 420 U/mg of protein, respectively. Molecular docking against horseradish peroxidase (1W4Y) showed compound 3e with the best binding energy (-6.561 kcal/mol), forming key hydrogen bonds (Asn135, Pro139) and a π-cation interaction with Arg38. These interactions suggest 3e may effectively inhibit hydrogen peroxide catalysis. The in silico assessment of the physicochemical properties, pharmacokinetics, and toxicology of synthesized compounds suggests that these compounds exhibit promising ADMET characteristics, with no identified toxicological concerns. [Display omitted] [ABSTRACT FROM AUTHOR] more...
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- 2025
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8. PHOTOPHYSICAL AND MORPHOLOGICAL PROPERTIES OF SYMMETRICAL SCHIFF BASES ASSEMBLED IN SPIN-COATED FILMS.
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CALDERA-VILLALOBOS, MARTÍN, HERRERA-GONZÁLEZ, ANA MARÍA, and COREÑO-ALONSO, OSCAR
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SCHIFF bases , *CONJUGATED polymers , *BAND gaps , *MOLECULAR structure , *POLYTHIOPHENES , *CHEMICAL engineering , *ISOXAZOLES , *SEMICONDUCTOR thin films , *INTERMOLECULAR forces , *TRIPHENYLAMINE - Published
- 2023
9. Competition of Thermodynamic and Kinetic Factors during the Formation of Stereoisomers of the Bis(chelate) Ni(II) Complexes Based on (N,O(S,Se))-Bidentate Azomethines: A Quantum Chemical Study.
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Kharabayev, N. N. and Minkin, V. I.
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CHELATES , *DENSITY functional theory , *MOLECULAR structure , *CHEMICAL models , *ISOMERS - Abstract
The molecular structures and relative energies of trans- and cis-isomers of low-spin bis(chelate) Ni(II) complexes based on (N,O(S,Se))-bidentate azomethines are calculated by the density functional theory. The mechanism of formation of the NiL2 complexes is studied in terms of the model of their step formation (Ni++ + (L)– → (NiL)+, (NiL)+ + (L)– → NiL2). The formation of the coordination sites NiN2O2, NiN2S2, and NiN2Se2 of the complexes is determined by the energy preference of one of possible configurations and also by the activation barriers of isomerization of the primary products formed at the initial step of the reaction of the starting components. [ABSTRACT FROM AUTHOR] more...
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- 2022
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10. Synthesis, Structure, Spectral-Luminescent Properties, and Biological Activity of Chlorine-Substituted N -[2-(Phenyliminomethyl)phenyl]-4-methylbenzenesulfamide and Their Zinc(II) Complexes.
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Burlov, Anatolii S., Vlasenko, Valery G., Milutka, Maxim S., Koshchienko, Yurii V., Makarova, Nadezhda I., Lazarenko, Vladimir A., Trigub, Alexander L., Kolodina, Alexandra A., Zubenko, Alexander A., Metelitsa, Anatoly V., Garnovskii, Dmitrii A., Gusev, Alexey N., and Linert, Wolfgang more...
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ZINC compounds synthesis , *THERMOGRAVIMETRY , *ZINC , *ZINC compounds , *DIFFERENTIAL scanning calorimetry , *ELEMENTAL analysis - Abstract
New azomethine compounds of 2-(N-tosylamino)benzaldehyde or 5-chloro-2-(N-tosylamino)benzaldehyde and the corresponding chlorine-substituted anilines, zinc(II) complexes based on them have been synthesized. The structures of azomethines and their complexes were determined by elemental analysis, IR, 1H NMR, X-ray spectroscopy, and X-ray diffraction. It is found that all ZnL2 complexes have a tetrahedral structure according to XAFS and X-ray diffraction data. The photoluminescent properties of azomethines and zinc complexes in methylene chloride solution and in solid form have been studied. It is shown that the photoluminescence quantum yields of solid samples of the complexes are an order of magnitude higher compared to the solutions and range from 11.34% to 48.3%. The thermal properties of Zn(II) complexes were determined by thermal gravimetric analysis (TGA) and differential scanning calorimetry. The TGA curves of all the compounds suggest their high thermal stability up to temperatures higher than 290 °C. The electrochemical properties of all complexes were investigated by the cyclic voltammetry method. The multilayered devices ITO/PEDOT:PSS/NPD/Zn complex/ TPBI/LiF/Al with wide electroluminescence (EL) color range spanning the range from bluish-green (494 nm) to green (533 nm) and the high values of brightness, current and power efficiency were fabricated. The biological activity of azomethines and zinc complexes has been studied. In the case of complexes, the protistocidal activity of the zinc complex with azomethine of 5-chloro-2-(N-tosylamino)benzaldehyde with 4-chloroaniline was two times higher than the activity of the reference drug toltrazuril. [ABSTRACT FROM AUTHOR] more...
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- 2022
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11. Spectroscopic and Physicochemical Investigations of Azomethines with Triphenylamine Core towards Optoelectronics.
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Amin, Muhammad Faisal, Gnida, Paweł, Kotowicz, Sonia, Małecki, Jan Grzegorz, Siwy, Mariola, Nitschke, Paweł, and Schab-Balcerzak, Ewa
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DENSITY functionals , *PHOTOVOLTAIC cells , *DIETHYL sulfate , *OPTOELECTRONICS , *CHEMICAL properties , *TRIPHENYLAMINE - Abstract
Three new azomethines based on triphenylamine with two or three substituents were obtained. Chemical structure and purity were confirmed by 1H NMR, FTIR elemental analysis and mass spectroscopy. The investigations were focused on the relationship between chemical structure and properties important for optoelectronic materials. Thus, the studies of thermal, optical and electrochemical properties were carried out based on differential scanning calorimetry, thermogravimetric analysis, electronic absorption, photoluminescence and cyclic voltammetry measurements. The ongoing consideration of experimental results was complemented by theoretical calculations using the density functional theory method. The donor activity of obtained compounds was tested in bulk-heterojuntion photovoltaic cells with structure ITO/PEDOT:PSS/imine:PCBM/Al and ITO/PEDOT:PSS/imine:P3HT:PCBM/Al). The effect of the presence of the amino-thiophene-3,4-dicarboxylic acid diethyl ester groups and various number of hexyloxyphenyl units on imines properties was demonstrated. [ABSTRACT FROM AUTHOR] more...
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- 2022
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12. Synthesis and Characterization of New Conjugated Azomethines End-Capped with Amino-thiophene-3,4-dicarboxylic Acid Diethyl Ester.
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Pająk, Agnieszka Katarzyna, Kotowicz, Sonia, Gnida, Paweł, Małecki, Jan Grzegorz, Ciemięga, Agnieszka, Łuczak, Adam, Jung, Jarosław, and Schab-Balcerzak, Ewa
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METHYLAMMONIUM , *DIETHYL sulfate , *GLASS transition temperature , *DENSITY functional theory , *LITHIUM , *SOLAR cells , *PEROVSKITE - Abstract
A new series of thiophene-based azomethines differing in the core structure was synthesized. The effect of the central core structure in azomethines on the thermal, optical and electrochemical properties was investigated. The obtained compounds exhibited the ability to form a stable amorphous phase with a high glass transition temperature above 100 °C. They were electrochemically active and undergo oxidation and reduction processes. The highest occupied (HOMO) and the lowest unoccupied molecular (LUMO) orbitals were in the range of −3.86–−3.60 eV and −5.46–−5.17 eV, respectively, resulting in a very low energy band gap below 1.7 eV. Optical investigations were performed in the solvents with various polarity and in the solid state as a thin film deposited on a glass substrate. The synthesized imines absorbed radiation from 350 to 600 nm, depending on its structure and showed weak emission with a photoluminescence quantum yield below 2.5%. The photophysical investigations were supported by theoretical calculations using the density functional theory. The synthesized imines doped with lithium bis-(trifluoromethanesulfonyl)imide were examined as hole transporting materials (HTM) in hybrid inorganic-organic perovskite solar cells. It was found that both a volume of lithium salt and core imine structure significantly impact device performance. The best power conversion efficiency (PCE), being about 35–63% higher compared to other devices, exhibited cells based on the imine containing a core tiphenylamine unit. [ABSTRACT FROM AUTHOR] more...
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- 2022
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13. New nano-fungicides for the management of sheath blight disease (Rhizoctonia solani) in rice.
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Siddhartha, Verma, Ankita, Bashyal, Bishnu Maya, Gogoi, Robin, and Kumar, Rajesh
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FUNGICIDES , *RHIZOCTONIA solani , *RICE sheath blight , *RICE , *TRANSMISSION electron microscopy , *DISEASE management - Abstract
Rice sheath blight, caused by Rhizoctonia solani, is one of the increasing concerns in rice causing severe economic losses worldwide. Chemical control measures are already in practice for the management of this disease but approach for discovery of new chemicals with improved disease control potential is essential. The present investigation involves the development of nanoformulations of halogen substituted azomethines as new potent fungicide for the management of sheath blight disease in rice. The halogen substituted azomethines were synthesized and screened for in-vitro bioefficacy. Then the azomethines were nanoformulated for their in-vivo pot culture evaluation against Rhizoctonia solani. Transmission electron microscopy confirmed the particle size of the developed nanoformulations in the range of 1–100 nm. In-vitro inhibition results of test compounds revealed their ED50 values in the range of 11.9 to 22.4 μg/ml with best performer 2,4,5-trichloro-N-(2,4-dichlorobenzylidene)aniline. 3-Chloro-N-(2,6-dichlorobenzylidene)-4-fluoroaniline displayed maximum in-vivo efficacy against R. Solani which was comparable with that of hexaconazole, a standard recommended fungicide. [ABSTRACT FROM AUTHOR] more...
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- 2022
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14. Zinc(II) Complexes with Azomethines of 2,4,6-Trimethylaniline and Halogen-Substituted Salicylaldehyde.
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Milutka, M. S., Burlov, A. S., Vlasenko, V. G., Koshchienko, Yu. V., Korshunova, E. V., Uraev, A. I., Trigub, A. L., Zubenko, A. A., Klimenko, A. I., and Gusev, A. N.
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ZINC compounds , *DICHLOROMETHANE , *SOLID solutions , *ZINC , *X-ray spectroscopy , *SCHIFF bases , *PHOTOLUMINESCENT polymers - Abstract
Azomethines were synthesized from 2,4,6-trimethylaniline, salicylaldehyde, and its 3(5)-halogen derivatives, as well as their complexes with zinc(II) (ZnL2). The structure and composition of the compounds were determined by elemental analysis, IR, 1H NMR, and X-ray spectroscopy. The ZnL2 complexes have a tetrahedral structure. The photoluminescent properties of azomethines and their zinc complexes in methylene chloride solutions and in solid state have been studied. The photoluminescence quantum yields of azomethines lie in the range 4.66–12.16%; for zinc complexes they decrease to 0.45–2.02%. The average photoluminescence lifetimes for azomethines and their complexes range from 2.00 to 2.87 ns. Azomethine, obtained from 2,4,6-trimethylaniline and dichlorosalicylic aldehyde, and its complex with zinc have significant protistocidal activity. [ABSTRACT FROM AUTHOR] more...
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- 2022
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15. Synthesis and studies of antimicrobial activity of azomethine crown ether derivatives and their copper complexes.
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Sadovskaya, N. Yu., Glushko, V. N., Blokhina, L. I., Belus', S. K., Retivov, V. M., Zhila, M. Yu., and Cherdynceva, T. A.
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CROWN ethers , *COPPER compounds , *ETHER derivatives , *ANTI-infective agents , *MICROCOCCUS luteus , *SCHIFF bases - Abstract
New Schiff bases were synthesized by condensation of 4-pyridinecarboxaldehyde with crown ethers (4-aminobenzo-15-crown-5, 4,4-diaminodibenzo-18-crown-6, and 4,4-diaminodibenzo-21-crown-7). Treatment of the synthesized azomethines with equimolar amount of copper(II) acetate gave the corresponding copper complexes. Antimicrobial activity of crown ethers and their derivatives against Gram-positive (Staphylococcus aureus, Micrococcus luteus) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria was studied. The effects of the substituents on antimicrobial activity of the ligands and their derivatives were analyzed. [ABSTRACT FROM AUTHOR] more...
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- 2022
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16. Targeted Synthesis and Analysis of Biologically Active Azomethine Derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
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A. S. Chiriapkin, I. P. Kodonidi, and M. V. Larsky
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azomethines ,2-amino-4 ,7-tetrahydro-1-benzothiophene-3-carboxamide ,molecular design ,pass ,synthesis of azomethines ,addition – elimination reaction ,hplc ,Pharmaceutical industry ,HD9665-9675 - Abstract
Introduction. Azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide are acyclic precursors of biologically active compounds derived from 5,6,7,8-tetrahydro-3H-benzoteopheno[2,3-d]pyrimidine-4-one. Examples of these groups of compounds with different pharmacological properties are given in the literature, but their cytostatic effect is mainly described. These data and the preparative availability allow us to judge the prospects for further study and molecular design in a number of azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide. Optimization of methods for the synthesis and analysis of substances of this series and the identification of structure-activity relationship are of considerable interest for medical chemistry and pharmaceutical science. The resulting leading compounds will allow us to further develop laboratory requirements for the synthesis of an active pharmaceutical substance.Aim. To make a predict, optimize the synthesis conditions and develop a method for high performance liquid chromatography (HPLC) analysis of pharmacologically active azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide.Materials and methods. The prediction of biological activity was carried out through the web resource PASS Online. The synthesis of the target azomethines was carried out by the interaction of aromatic aldehydes with 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide in an ethanol. The reaction was monitored by thin-layer chromatography (TLC). The determination of related impurities was done by HPLC. The analysis was carried out under the conditions of isocratic elution with a mobile phase of acetonitrile – water (70:30).Results and discussion. The results of the prediction of the biological activity of the constructed structures suggest the manifestation of cytostatic, antitubercular and anti-inflammatory activity characteristic of all target azomethines. The analysis of the reactivity revealed the influence of substituents of aldehydes contained in the aromatic core on the completeness of the condensation reaction. The spectral characteristics clearly confirmed the structure of the products, and the HPLC results showed the purity of the obtained substances, which is more than 95 %.Conclusion. As a result of the conducted studies, the structure of promising azomethine derivatives of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide was justified and the method of their synthesis and analysis by HPLC was optimized. In the future, the results of the research will allow us to identify the leading compounds with the specified pharmacological properties. more...
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- 2021
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17. Crystal structure and Hirshfeld surface analysis of 3-[(1E)-(4-{4-[(E)-(3-hydroxybenzylidene)amino]phenoxy}phenylimino)methyl]phenol
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Shaaban K. Mohamed, Joel T. Mague, Mehmet Akkurt, Farouq E. Hawaiz, Sahar M. I. Elgarhy, and Elham A. Al-Taifi
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crystal structure ,hydrogen bond ,phenol ,aromatic ether ,phenoxy ,azomethines ,hirshfeld surface analysis ,Crystallography ,QD901-999 - Abstract
In the crystal, the molecule of the title compound, C26H20N2O3, has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O—H...N and C—H...O hydrogen bonds. Between the layers, C—H...π interactions are observed. more...
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- 2021
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18. HYDROGEN BONDING IN THE CRYSTAL OF 1,1′-((1E,1′E)-(PYRIDINE-3,4-DIYLBIS (AZANYLYLIDENE))BIS(METHANYLYLIDENE))- BIS(NAPHTHALEN-2-OL) ACETONITRILE SOLVATE: COMBINED EXPERIMENTAL AND THEORETICAL STUDY.
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Mardaleishvili, I. R., Vologzhanina, A. V., Novikov, A. S., Shienok, A. I., Kol′tsova, L. S., Zaichenko, N. L., Nadtochenko, V. A., and Tskhovrebov, A. G.
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HYDROGEN bonding , *ACETONITRILE , *ELECTRON density , *ELECTRON distribution , *HYDROGEN atom , *SCHIFF bases - Abstract
The title compound, 1,1′-((1E,1′E)-(pyridine-3,4-diylbis(azanylylidene))bis(methanylylidene))bis (naphthalen-2-ol) (1), was synthesized and structurally characterized. The compound cocrystallized with one MeCN molecule. Interestingly, one of two salicylaldehyde Schiff base fragments exists in enol form, while the other one - in a ketone form. Moreover, cocrystallized acetonitrile molecule forms hydrogen bonding with three hydrogen atoms of the dye molecule. The nature and energies of intermolecular and intramolecular hydrogen bonds were studied theoretically using DFT calculations and topological analysis of the electron density distribution within the formalism of Bader′s theory (QTAIM method). [ABSTRACT FROM AUTHOR] more...
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- 2022
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19. SYNTHESIS AND CRYSTAL STRUCTURE OF COBALT(III) COMPLEXES WITH SUBSTITUTED 2-[(BENZIMIDAZOLE-1-YL) IMINOMETHYL]PHENOLS.
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Burlov, A. S., Kuzmenko, T. A., Vlasenko, V. G., Koshchienko, Yu. V., Mashchenko, S. A., Chaltsev, B. V., Kolodina, A. A., and Kiskin, M. A.
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CRYSTAL structure , *COBALT , *PHENOLS , *MOLECULAR crystals , *PHENOL , *COBALT compounds - Abstract
Two Co(III) complexes are synthesized based on 2-{(E)-[2-(hydroxy(alkyl)amino)benzimidazole-1-yl]iminomethyl}phenol (H3L1 and H3L2, alkyl is ethyl or propyl). By the elemental analysis and IR spectroscopy it is established that the obtained complexes have the compositions [Co(H2L1)(HL1)]·2C2H5OH and [Co(H2L2)(HL2)]CH3OH·1/2H2O. Their crystal and molecular structures are determined by single crystal X-ray diffraction (XRD). From the XRD data it is found that the complexes crystallize in the triclinic space group as solvates with alcohol and water molecules. In mononuclear molecules of both complexes, two trischelate ligands in mono- and dianionic forms are coordinated to the Co(III) cation. The coordination environment of the cobalt atom CoN4O2 corresponds to a distorted octahedron in both compounds. [ABSTRACT FROM AUTHOR] more...
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- 2021
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20. СИНТЕЗ И СТРУКТУРНЫЕ ИССЛЕДОВАНИЯ АЗОМЕТИНОВ И АМИДОВ - ИСХОДНЫХ СОЕДИНЕНИЙ ДЛЯ СИНТЕЗА БЕНЗОКСАЗОЛОВ.
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ПУЛАТОВА, З. Ж., ХУРРАМОВ, А. Р., БОБАКУЛОВ, Х. М., and ЭЛМУРАДОВ, Б. Ж.
- Abstract
Background. Azomethines are known to be important intermediates for the preparation of benzoxazoles, which are biologically active compounds. Therefore, the development of methods for the synthesis of substituted azomethines is topical. Purpose: carrying out reactions of (substituted) aminophenols with aromatic aldehydes under various conditions and determining the factors affecting the type of products, determining their structures. Methodology. The reactions of 2-aminophenol, 4-nitro-2-aminophenol, 4-chloro-2-aminophenols with aldehydes were carried out under various conditions. As a result, azomethine and acetamide were obtained in high yields instead of the expected 2-arylbenzoxazoles. The structure of the synthesized substances was proved on the basis of the results of 1Hba 13C NMR spectroscopy and X-ray diffraction analysis. Originality: The synthesis of azomethines, components of the synthesis of heterocyclic compounds, was carried out. It was found that the condensation of aminophenols and aromatic aldehydes can proceed in different directions. Findings. Azomethine amides have been synthesized in high yields and are widely used for the synthesis of substituted benzoxazoles. The 1H and 13C NMR spectra of the obtained substances were analyzed, as well as the X-ray diffraction data of single crystals, and their chemical structures were established. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
21. Spectral and Luminescent Properties of Bis(azomethine) Based on 2-Hydroxy-1-Naphthaldehyde and 2,3-Diaminopyridine.
- Author
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Mardaleishvili, I. R., Kol'tsova, L. S., Zaichenko, N. L., Krutius, O. N., and Shienok, A. I.
- Subjects
- *
GROUP formation , *LUMINESCENCE , *YLIDES , *PYRIDINE , *MOIETIES (Chemistry) , *SCHIFF bases , *PYRIDINE derivatives - Abstract
The spectral and luminescent properties of solutions of bis(hydroxynaphthoazomethine) of the pyridine family have been studied in comparison with the analogue of the benzene family. The presence of the pyridine nitrogen atom in the ortho position to the azomethine group favors the formation of the keto form of the azomethine moiety in the ground state of the molecule. The position of the luminescence maxima of solutions weakly depends on the presence of a nitrogen atom in the heterocycle and is more determined by the solvent polarity. Longer-wavelength and more efficient luminescence is observed in polar media. [ABSTRACT FROM AUTHOR] more...
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- 2021
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22. Synthesis, Structure, Spectral-Luminescent Properties, and Biological Activity of Chlorine-Substituted Azomethines and Their Zinc(II) Complexes.
- Author
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Milutka, M. S., Burlov, A. S., Vlasenko, V. G., Koshchienko, Yu. V., Makarova, N. I., Metelitsa, A. V., Korshunova, E. V., Trigub, A. L., Zubenko, A. A., and Klimenko, A. I.
- Subjects
- *
ELEMENTAL analysis , *ZINC compounds , *DICHLOROMETHANE , *ZINC , *X-ray spectroscopy , *PHOTOLUMINESCENT polymers - Abstract
A number of chlorine-substituted azomethines of 2-hydroxybenzaldehydes and their zinc(II) complexes were synthesized. Structure of azomethines and zinc complexes was established by elemental analysis, IR, 1H NMR, and X-ray spectroscopy data. Complexes ZnL2 have a tetrahedral structure. The complexes exhibit weak photoluminescent properties in methylene chloride, whereas the photoluminescence quantum yields of the solid complexes are 100 times higher. Biological activity of the azomethines and zinc complexes was studied. [ABSTRACT FROM AUTHOR] more...
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- 2021
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23. Local Atomic Structure and Magnetic Properties of Cu(II), Co(II), and Zn(II) 1-(2-Hydroxybenzylidenamino)benzimidazolinone-2 Complexes.
- Author
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Vasilchenko, I. S., Vlasenko, V. G., Kuzmenko, T. A., Divaeva, L. N., Borodkin, G. S., Levchenkov, S. I., Zaichenko, S. B., Korshunova, E. V., Chalsev, B. V., and Burlov, A. S.
- Abstract
New azomethine 1-(2-hydroxybenzylidenamino)benzimidazolinone-2 and Cu(II), Co(II) and Zn(II) complexes based on it are synthesized and studied. The structure of azomethine and metal complexes is found from the data of elemental analysis, infrared (IR) spectroscopy,
1 H NMR spectroscopy, X-ray absorption spectroscopy, and magnetochemistry. It is shown that all complexes have a mononuclear structure with the general formula M(HL)2 . For the copper complex, the weak antiferromagnetic-type exchange between copper ions is observed due to the formation of intermolecular hydrogen bonds N–H···O=C. [ABSTRACT FROM AUTHOR] more...- Published
- 2021
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24. Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate
- Author
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Ayalew Wodajo, Alexander G. Tskhovrebov, Tuan Anh Le, Alexey S. Kubasov, Maria M. Grishina, Oleg N. Krutius, and Victor N. Khrustalev
- Subjects
azomethines ,imines ,hydrogen bonding ,weak interactions ,excited-state intramolecular proton transfer ,crystal structure ,Crystallography ,QD901-999 - Abstract
The bis(anil) molecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H...N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H...O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H...O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H...Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase. more...
- Published
- 2020
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25. Reactions of Pyridoxal Derivatives with Phenyl Iso(thio)cyanates.
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Kibardina, L. K., Trifonov, A. V., Dobrynin, A. B., Burilov, A. R., and Pudovik, M. A.
- Subjects
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CYANATES , *GROUP formation , *HYDROXYMETHYL compounds , *SCHIFF bases , *PARTICIPATION - Abstract
The reaction of phenyl isocyanate with pyridoxal is carried out with the participation of hydroxymethyl and phenolic groups with the formation of dicarbamate derivatives. The reactions of pyridoxal azomethines with phenyl isocyanate, depending on the structure and the ratio of the starting reagents, lead to the formation of mono-, di- or tricarbamate derivatives. The product of addition of azomethine pyridoxal to phenyl isocyanate with the participation of a hydroxymethyl group was obtained. [ABSTRACT FROM AUTHOR] more...
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- 2021
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26. Unsymmetrical Pyridoxal-Based Bisazomethines.
- Author
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Bagautdinova, R. H., Kibardina, L. K., Burilov, A. R., and Pudovik, M. A.
- Subjects
- *
AROMATIC aldehydes , *HYDROCHLORIC acid , *SCHIFF bases - Abstract
The reaction of equimolar amounts of pyridoxal and 1,2-propylenediamine leads to the formation of monoimine, which exists as a cyclic imidazolidine tautomer. The latter reacts with aromatic aldehydes to form unsymmetric bisazomethines. The reaction of azomethine with phenylisocyanate produces a compound containing a carbamate group, and the reaction with hydrochloric acid leads to the formation of a salt-based furopyridine. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
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27. Synthesis of Dihydrochlorides of Azaadamantanes Containing 8-Hydroxyquinoline Fragments and their Antibacterial Activity in Mice with Dysentery and Staphylococcal Infections.
- Author
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Harutyunyan, G. L., Harutyunyan, A. D., Gevorkyan, K. A., Paronikyan, R. V., Stepanyan, G. M., and Gasparyan, S. P.
- Subjects
- *
STAPHYLOCOCCAL diseases , *DYSENTERY , *CHEMICAL synthesis , *MICE , *SCHIFF bases - Abstract
New azaadamantane derivatives containing 8-hydroxyquinoline fragments were synthesized. Their antibacterial activity was studied. The synthesized compounds exhibited high antibacterial activity in vitro. The 6-oxo-5,7-diethyl- and 5,7-dimethyl-2-(8'-hydroxyquinolyl-5')-1,3-diazaadamantane dihydrochlorides showed therapeutic effects in mice with dysentery and staphylococcal infections. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
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28. IDENTIFICATION OF SUPRAMOLECULAR DIMERS IN THE CRYSTAL STRUCTURE OF (Z)-1-(((5-FLUOROPYRIDIN-2-YL)AMINO)METHYLENE)NAPHTHALEN-2(1H)-ONE via C(sp2)–H⋯F HYDROGEN BONDING: A COMBINED EXPERIMENTAL AND THEORETICAL STUDY.
- Author
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Tskhovrebov, A. G., Novikov, A. S., and Khrustalev, V. N.
- Subjects
- *
CRYSTAL structure , *ELECTRON distribution , *HYDROGEN bonding , *INTERMOLECULAR interactions , *ATOMS in molecules theory , *ELECTRON density , *DIMERIZATION - Abstract
Title compound C16H11FN2O (1) is nearly planar, and adopts the keto-amine form with a strong intramolecular N–H⋯O hydrogen bond. Interestingly, the compound features an intramolecular C–H⋯N weak interaction in the crystal. In addition, the molecules of 1 form supramolecular dimers via C–F⋯H–C13 weak interactions. The nature and energies of intermolecular noncovalent interactions, which are responsible for the supramolecular dimerization, are studied theoretically using DFT calculations, and the topological analysis of the electron density distribution is performed within the formalism of Bader′s theory (QTAIM method). [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
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29. Crystal structure and Hirshfeld surface analysis of 3-[(1E)-(4-{4-[(E)-(3-hydroxybenzylidene)amino]-phenoxy}phenylimino)methyl]phenol.
- Author
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Mohamed, Shaaban K., Mague, Joel T., Akkurt, Mehmet, Hawaiz, Farouq E., Elgarhy, Sahar M. I., and Al-Taifi, Elham A.
- Subjects
CRYSTAL structure ,SURFACE analysis ,SURFACE structure ,HYDROGEN bonding ,CRYSTALS - Abstract
In the crystal, the molecule of the title compound, C
26 H20 N2 O3 , has crystallographically imposed twofold rotation symmetry. The crystal packing consists of layers parallel to the ab plane formed by O--H N and C--H O hydrogen bonds. Between the layers, C--H π interactions are observed. [ABSTRACT FROM AUTHOR] more...- Published
- 2021
- Full Text
- View/download PDF
30. Tetra-, Penta-, and Hexacoordinate Stereoisomers of the Bis(ligand) Complexes of Zn(II) and Cd(II) Based on (N,O,S(Se))-Tridentate Azomethines. A Quantum Chemical Study.
- Author
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Kharabayev, N. N.
- Abstract
The molecular structures and relative energies of tetra-, penta-, and hexacoordinate stereoisomers of the Zn(II) and Cd(II) bis(ligand) complexes based on (N,O,Y (Y = S, Se))-tridentate azomethines (coordination nodes of the competing stereoisomers are MN2O2, MN2O2Y, and MN2O2Y2, respectively) are calculated by the density functional theory and nonempirical Hartree–Fock method. The simulation of the mechanism for the formation of the tetra-, penta-, and hexacoordinate stereoisomers with allowance for the subsequent stereoisomerization makes it possible to establish the preferable tetracoordination (as a pseudotetrahedron) for the zinc complexes and penta- or hexacoordination for the cadmium complex depending on the specific features of the ligand structure. [ABSTRACT FROM AUTHOR] more...
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- 2021
- Full Text
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31. New Schiff bases from 2,5-bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde.
- Author
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Verochkina, Ekaterina A., Vchislo, Nadezhda V., and Larina, Ludmila I.
- Subjects
- *
SCHIFF bases , *ELEMENTAL analysis , *AMINO acids , *AMINES , *DATA analysis - Abstract
Novel densely functionalized Schiff bases have been synthesized by the reaction of 2,5-bis-(butylsulfanyl)-2,3-dihydro-4H-pyran-2-carbaldehyde with primary amines and amino acids. Structure of the obtained compounds is confirmed using the data of elemental analysis, IR and NMR techniques, and chromatomassspectrometry. [ABSTRACT FROM AUTHOR] more...
- Published
- 2021
- Full Text
- View/download PDF
32. Study of 1,3-dipolar cycloaddition of amino-acid azomethines and Juglone.
- Author
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Syngaevsky, Vadym, Karkhut, Andrew, Polovkovych, Sviatoslav, Gzella, Andrzej, Lesyk, Roman, and Novikov, Volodymyr
- Subjects
- *
RING formation (Chemistry) , *ISOXAZOLIDINES , *X-ray spectra , *X-ray diffraction - Abstract
Novel 2,3,4,9-tetrahydro- and 4,9-dihydro-1H-benzofisoindole derivatives were synthesized from Juglone and amino-acid azomethines in 74–85% yields via 1,3-dipolar cycloaddition. The stereo- and regioselectivity of cycloaddition was confirmed by NMR spectra and single-crystal X-ray diffraction analysis. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
33. Crystal structure of 1,1'-{(1E,1'E)-[4,4'-(9H-fluorene- 9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis- (methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate.
- Author
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Wodajo, Ayalew, Tskhovrebov, Alexander G., Le, Tuan Anh, Kubasov, Alexey S., Grishina, Maria M., Krutius, Oleg N., and Khrustalev, Victor N.
- Subjects
CRYSTAL structure ,HISTONE deacetylase ,STACKING interactions ,DIHEDRAL angles ,HYDROGEN bonding ,INTRAMOLECULAR forces ,DECARBOXYLASES - Abstract
The bis(anil) molecule of the title compound, C
47 H32 N2 O2 C6 H4 C2 , contains two anil fragments in the enol--enol form, exhibiting intramolecular O--H N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8) between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10) with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C--H O interactions. The dimers arrange in a onedimensional column along the b axis via another C-H O interaction and a stacking interaction between the hydroxynaphthalene ring system with a centroid-centroid distance of 3.6562 (16) A. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C--H Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase. [ABSTRACT FROM AUTHOR] more...- Published
- 2020
- Full Text
- View/download PDF
34. Theoretical, spectroscopical, and experimental investigations of small azomethine molecules for organic solar cells.
- Author
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Yorur Goreci, Cigdem
- Subjects
- *
SOLAR cells , *SMALL molecules , *MOLECULAR shapes , *LIQUID chromatography-mass spectrometry , *MOLECULAR orbitals , *SCHIFF bases , *PHOTOSENSITIZERS , *CONDENSATION - Abstract
Small azomethine molecules (4,4′-bis((2-hydroxy-4-octyloxyphenyl)methylimino)diphenylmethane (BP-DPM) and 4,4′-bis((2-hydroxy-4-octyloxyphenyl)methylimino)diphenyl ether (BP-DPE)) for photovoltaic applications were synthesized by condensation of appropriate arylaldehydes and arylendiamines and characterized using Fourier-transform infrared spectroscopy, 1H NMR, 13C NMR, and liquid chromatography–mass spectrometry. Azomethine molecules are additives in organic solar cells. The effect of a possible energy transfer between BP-DPE and P3HT on the photovoltaic performance of devices employing ternary blends of BP-DPE :P3HT: phenyl-C61-butyric acid methyl ester (PCBM) was investigated by absorption and emission spectra. The devices employing BP-DPE :P3HT:PCBM with 1:4 ratio exhibited a Jsc of 4.2 mA cm−2, Voc of 575 mV, and FF of 0.27 which led to a power conversion efficiency (PCE) of 0.65%. In addition, density functional theory calculations (DFT/B3LYP/6-31G(d)) were used to determine the optimized molecular geometry, highest occupied molecular orbital–lowest unoccupied molecular orbital energies, electronic structures, and the molecular electrostatic potential surfaces of the molecules. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
35. Synthesis of New C-Alkyl-N-pyridoxylmethylbenzimidazoles.
- Author
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Bagautdinova, R. Kh., Aitbay, G. N., Kibardina, L. K., Strelnik, A. G., Burilov, A. R., and Pudovik, M. A.
- Subjects
- *
ALDEHYDES , *IMINES , *BENZIMIDAZOLES - Abstract
The reactions of pyridoxal monoimine based on ortho-phenylenediamine with aliphatic aldehydes results in the formation of new C-alkyl-N-pyridoxylmethylbenzimidazoles. [ABSTRACT FROM AUTHOR]
- Published
- 2020
- Full Text
- View/download PDF
36. Heterocyclic Derivatives of 4-Amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one.
- Author
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Akishina, E. A., Kazak, D. V., Dikusar, E. A., Zalesskaya, E. G., Zhukovskaya, N. A., Stepin, S. G., and Potkin, V. I.
- Subjects
- *
NIACIN , *PYRAZOLONES - Abstract
A convenient and scalable preparative method for the synthesis of azomethines from 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one and substituted benzaldehydes, as well as 1,2-oxazole and 1,2-thiazolecarbaldehyde was developed. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
37. Synthesis and Study of Framework Azomethine Compounds as Ingredients of Rubber Stocks.
- Author
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Kochetkov, V. G., Burmistrov, V. V., D'yachenko, V. S., Rasskazova, E. V., Novopol'tseva, O. M., and Butov, G. M.
- Subjects
- *
SCHIFF bases , *RUBBER , *VULCANIZATION , *THERMAL resistance , *DIAMINES - Abstract
Bisazomethines derived from D,L-camphor, 2-adamantanone, and aliphatic diamines were prepared. The possibility of using bisazomethines as vulcanization accelerators was examined. The physicomechanical parameters of vulcanizates based on SKI-3 and their resistance to thermal oxidative aging were determined. The influence of the bisazomethine structure on the vul canization rate was found. Among the compounds synthesized, N,N′-(propane-1,3-diyl)bis(1,7,7-trimethylbicyclo[2.2.1]heptan-2-imine) shows the best set of vulcanization and operation properties. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
38. Synthesis of new phenolic compounds and biological evaluation as antiproliferative agents.
- Author
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Ibrahim, Marwa A, George, Riham F, Abou-Seri, Sahar M, and El-Moghazy, Samir M
- Subjects
- *
PHENOLS , *NON-small-cell lung carcinoma , *BRAIN tumors , *CELL lines - Abstract
New series of phenolic azomethine compounds in addition to 5-arylidene thiazolidinones are synthesized and screened for their anticancer activity against the brain cancer cell line SNB-75 and non-small lung cancer cells HOP-92. The azomethine derivative 12b is the most active compound against SNB-75 displaying an IC50 value of 0.14 μM. Compounds 7b, 16a and 27d display submicromolar activity against the HOP-92 cell line with IC50 values of 0.73, 0.74 and 0.81 μM, respectively. Moreover, studying the cytotoxic effects of the most active compounds against normal lung cells WI-38 revealed that compounds 7b, 16a and 27d showed high safety profiles as anticancer agents. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
39. Synthesis and characterization of two new TiO2-containing benzothiazole-based imine composites for organic device applications
- Author
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Anna Różycka, Agnieszka Iwan, Krzysztof Artur Bogdanowicz, Michal Filapek, Natalia Górska, Damian Pociecha, Marek Malinowski, Patryk Fryń, Agnieszka Hreniak, Jakub Rysz, Paweł Dąbczyński, and Monika Marzec more...
- Subjects
azomethines ,composites ,HOMO-LUMO ,imines ,organic devices ,TiO2 ,Technology ,Chemical technology ,TP1-1185 ,Science ,Physics ,QC1-999 - Abstract
The effect of the presence of titanium dioxide in two new imines, (E,E)-(butane-1,4-diyl)bis(oxybutane-4,1-diyl) bis(4-{[(benzo[d][1,3]thiazol-2-yl)methylidene]amino}benzoate) (SP1) and (E)-N-[(benzo[d][1,3]thiazol-2-yl)methylidene]-4-dodecylaniline (SP2), on the properties and stability of imine:TiO2 composites for organic device applications were examined. The investigated titanium dioxide (in anatase form, obtained via the sol–gel method) exhibited a surface area of 59.5 m2/g according to Brunauer–Emmett–Teller theory, and its structure is a combination of both meso- and microporous. The average pore diameter calculated by the Barrett–Joyner–Halenda method was 6.2 nm and the cumulative volume of pores was 0.117 m3/g. The imine SP1 exhibited columnar organization (Col), while SP2 revealed a hexagonal columnar crystalline phase (Colhk). The imine:TiO2 mixtures in various weight ratio (3:0, 3:1, 3:2, 3:3) showed a lower energy gap and HOMO–LUMO energy levels compared to pure TiO2. This implies that TiO2 provides not only a larger surface area for sensitizer adsorption and good electron collection, but also causes a shift of the imine energy levels resulting from intermolecular interaction. Also the temperature of the phase transition was slightly affected with the increase of TiO2 concentration in imine-based composites. The changes observed in the Fourier transform middle-infrared absorption (FT-MIR) spectra confirmed the significant influence of TiO2 on structural properties of both investigated imines. Similar interactions of oxygen vacancies existing on the TiO2 surface with SP1 and SP2 were observed. The imine:TiO2 mixtures showed good air stability and reusability, which demonstrates its potential for organic device applications. more...
- Published
- 2018
- Full Text
- View/download PDF
40. Photoredox Fluoroalkylation of Arylidene and Alkylidene Amidrazones.
- Author
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Supranovich, Vyacheslav I., Chernov, Grigory N., Levin, Vitalij V., and Dilman, Alexander D.
- Subjects
- *
BLUE light , *CARBAZOLE , *ALDEHYDES , *CONDENSATION - Abstract
A method for the photoredox fluoroalkylation of the C–H bond of azomethine compounds obtained from condensation of aldehydes and N‐methylpyrrolidinone‐derived amidrazones is described. The reactions are promoted with a carbazole‐based organic photocatalyst under blue light irradiation. The ability of the cyclic nitrogen to stabilize a nitrogen‐centered radical is believed to be a key factor responsible for the reaction efficiency. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
41. Switchable Luminescence of New Compounds Based on Imidazoles and Azomethines.
- Author
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Mardaleishvili, I. R., Lyubimova, G. V., Lyubimov, A. V., Kol'tsova, L. S., Shienok, A. I., Levin, P. P., Tatikolov, A. S., and Zaichenko, N. L.
- Subjects
- *
LUMINESCENCE , *LUMINOPHORES , *MASS media , *WAVELENGTHS , *COUMARINS , *ALCOHOL - Abstract
The spectral and luminescent properties of compounds A3–SA, A4–o–SA, and A4–o–K have been studied, whose structures include moieties of triphenylimidazole A3, tetraphenylimidazole A4, and hydroxyazomethines salicylideneaniline SA and coumarin-substituted azomethine K. Due to electronic conjugation of moieties, the compound A3–SA exhibits switchable luminescence only in alcohol solutions, whereas independent behavior of the moieties is observed in the case of linking of these luminophores by an oxygen bridge and luminescence switching by changing the excitation wavelength is possible both in solutions and polymeric media. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
- Full Text
- View/download PDF
42. Novel R3M (M = Si, Ge) substituted furan and thiophene-derived aldimines: Synthesis, electrochemistry, and biological activity.
- Author
-
Spura, Jana, Farhati, Amel, Romanovs, Vitalijs, Borodulin, Artyom, Belakovs, Sergejs, Popelis, Juris, Shestakova, Irina, Dammak, Mohamed, and Jouikov, Viatcheslav
- Subjects
- *
ALDIMINES , *ELECTROCHEMISTRY , *THIOPHENES , *SILYL group , *REDUCTION potential , *FRONTIER orbitals , *ELECTROLYTIC reduction - Abstract
New furan and thiophene derivatives of aldimines o -HO-C 6 H 4 N CHC 4 H 4 X(R) (X = O, S; R = H, SiMe 3 , SiEt 3 , GeMe 3 , GeEt 3) were synthesized by condensation of o -aminophenol with the substituted aldehyde precursor. Their structure, electrochemical reduction/oxidation (in CH 3 CN/0.1 M Bu 4 NPF 6), frontier orbital energies, and cytotoxicity have been studied. Their electrochemical redox potentials E p show good correlation with the corresponding orbital energies and the difference E p ox – E p red corresponds well to their orbital hardness. These new compounds have a pronounced cytotoxicity toward cancer cells of human fibrosarcoma HT-1080 and mouse hepatoma MG-22A (IC 50 ≅ 1–8 μg ml−1) that can be modulated by introducing a Me 3 M substituent into the fifth position of the heterocycle (e.g., IC 50 (Me 3 Si)/IC 50 (H) ≥ 50). R 3 M-substitution reduces the orbital hardness of the aldimines studied and facilitates oxidation, promoting their oxidative metabolism. The neighboring group effect in the α-Me 3 Si-substituted thiophene derivative favors S-oxidation, which supposedly makes its metabolic mechanism different compared to R 3 M-substituted furan series (or for M = Ge in the thiophene series). Interestingly, SiMe 3 and GeMe 3 groups in both heterocyclic series (furan and thiophene) cause opposite trends in cytotoxicity, while the silyl group increases it, the germyl group decreases it. [ABSTRACT FROM AUTHOR] more...
- Published
- 2019
- Full Text
- View/download PDF
43. Controlled Molecular Magnetism of Bi- and Polynuclear Transition Metal Complexes Based on Hydrazones, Azomethines, and Their Analogs.
- Author
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Lukov, V. V., Shcherbakov, I. N., Levchenkov, S. I., Tupolova, Yu. P., Popov, L. D., Pankov, I. V., and Posokhova, S. V.
- Subjects
- *
SINGLE molecule magnets , *HYDRAZONES , *COORDINATION compounds , *CHEMICAL structure , *INTERMOLECULAR interactions , *TRANSITION metal complexes - Abstract
The possibilities of the magnetochemical method for the description of structures and properties of bi- and tetranuclear metallochelates and supramolecular architectures based on coordination compounds with restricted types of ligand systems, mainly hydrazones, azomethines, and their analogs, are reviewed. The known published data for the bi- and polynuclear complexes, whose paramagnetic centers are bound by both intra- and intermolecular exchange interactions, are systematized. A relationship between specific features of the electronic and geometric structures of the complexes and the character of the exchange effects is considered. Magnetostructural relations in the discussed compounds are systematized. The compounds discussed are important model objects for the development of the strategy for the targeted design of one-, two-, and three-dimensional magnetically ordered structures. [ABSTRACT FROM AUTHOR] more...
- Published
- 2019
- Full Text
- View/download PDF
44. Theoretical Modeling of the Structure of N-[2-[(Hydroxyalkylimino)Methyl]Phenyl]-4-Methylbenzene-Sulfamides and Their Mono- and Binuclear Copper(II) Complexes.
- Author
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Burlov, A. S., Starikova, A. A., Vlasenko, V. G., and Koshchienko, Yu. V.
- Subjects
- *
COORDINATION compounds , *MAGNETIC structure , *AMINO alcohols , *SCHIFF bases , *MAGNETIC properties , *METHYLENE group - Abstract
The paper presents a theoretical DFT UB3LYP/6-311++G(d,p) modeling of the structure and magnetic properties of Cu(II) coordination compounds with tridentate Schiff bases derived from 2-tosylaminobenzaldehyde and amino alcohols. It is shown that the elongation of the aliphatic chain in the amine part of ligand systems prevents the formation of binuclear metal-chelate structures. At the same time, mononuclear bis-chelate complexes, as well as mono-adducts containing a coordinated solvent molecule and a tridentate azomethine compound, are formed regardless of the number of methylene units. [ABSTRACT FROM AUTHOR] more...
- Published
- 2019
- Full Text
- View/download PDF
45. Mesomorphic Behavior of Symmetric Azomethine Dimers Containing Different Chromophore Groups
- Author
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Elena Perju and Luminita Marin
- Subjects
symmetrical dimers ,azomethines ,thermotropic liquid crystals ,mesomorphic glass ,optical properties ,Organic chemistry ,QD241-441 - Abstract
A series of new azomethine dimers was synthesized by the condensation reaction of flexible bis-benzaldehydes with four aromatic amines containing phenyl, naphthyl, anthracene and pyrene groups. Their right structure was confirmed by FTIR and 1H-NMR spectroscopy and their thermal properties were investigated by thermogravimetric analysis, differential scanning calorimetry and polarized light optical microscopy. A view on their photophysical behavior was gained by UV-vis and photoluminescence spectroscopy. The dimers containing pyrene and anthracene presented liquid crystalline behavior, while the other dimers were crystalline compounds. Two dimers containing pyrene moieties formed mesomorphic glasses and had intense luminescence, promising properties for applications in building optoelectronic devices. more...
- Published
- 2021
- Full Text
- View/download PDF
46. Zinc(II) and nickel(II) complexes with N-[2-(2-diethylphoshponylethyliminomethyl)phenyl]-4-methylbenzenesulfonamide: Synthesis, structure, and photoluminescence properties.
- Author
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Burlov, Anatolii S., Vlasenko, Valery G., Popov, Leonid D., Koshchienko, Yurii V., Garnovskii, Dmitrii A., Kolodina, Alexandra A., Korshunova, Evgeniya V., Zubavichus, Yan V., and Lazarenko, Vladimir A. more...
- Subjects
- *
NICKEL , *PHOTOLUMINESCENCE , *SCHIFF bases , *X-ray crystallography , *ZINC , *ULTRAVIOLET-visible spectroscopy , *ZINC compounds synthesis , *PHOTOLUMINESCENT polymers - Abstract
[Display omitted] • Two novel Schiff base Zn(II) and Ni(II) complexes were prepared. • The structures of the compounds were established by X-ray crystallography. • The photoluminescent properties of Schiff base and Zn(II) complex were investigated. Two Zn(II) and Ni(II) complexes derived from the N -[2-(2-diethylphosphonylethyliminomethyl)phenyl]-4-methylbenzenesulfonamide ligand (HL) with stoichiometry ML 2 (M = Zn, Ni) have been synthesized. Their structures have been established using elemental analysis, IR, 1H NMR, UV–Vis spectroscopy, and synchrotron single-crystal X-ray diffraction. The Zn(II) and Ni(II) metal sites therein adopt the tetrahedral configuration. The DMSO and toluene solutions of the Zn(II) complex manifest photoluminescence in the blue-violet spectral range characterized by PL maxima at 436 and 432 nm and quantum yields of 0.15 and 0.30, respectively. [ABSTRACT FROM AUTHOR] more...
- Published
- 2023
- Full Text
- View/download PDF
47. COLORING PROPERTIES OF WOOL FABRIC COLORED BY NEW DYESTUFFS - AZOMETHINES
- Author
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DJORDJEVIC Dragan, SMELCEROVIC Miodrag, MICIC Aleksandra, AMIN Goran, and MILIC Dragan
- Subjects
Azomethines ,Dyestuff ,Coloring ,Wool ,CIEL*a*b ,Manufactures ,TS1-2301 - Abstract
The azomethines have broad applications in food and dyestuff industries, and in analytical chemistry, catalysis and also in the field of agrochemical. These have played an influential part in the improvement of modern coordination chemistry, but also they can also be found at key points in the development of inorganic biochemistry, catalysis and also in optical materials. The present paper describes coloring properties of wool fabric colored by new dyestuffs - azomethines, derivate of isatin. Synthesizing of dyestuffs can often have one to six chromogen, which can be defined as the photoactive components that contain colored or uncolored absorbent components. In addition of monoazo, diazo, poly-azo, anthraquinone, xanthan and similar systems, the azomethines or imines, also includes to the chromogen groups. Azomethines, such as, isatin-3-hydrazone, isatin-3-thiosemicarbazone and isatin-3-phenylhydrazone, were synthesized and their coloring performance on wool fabric assessed. The synthesized azomethines showed very good substantively for wool fibers with good coloring performance according to CIEL*a*b* system which characterized quantitative and qualitative coloring property. Dyestuff 3 or isatin-3-phenylhydrazone bound to woolen textiles to a greater extent and greater intensity (minimum value of L). Dyestuff 2 or isatin-3-thiosemicarbazone linked to the minimum amount for textiles (the largest value of L). Although it must be noted that it is a lighter shade (yellow color) as opposed to the dyestuff 3 (red color). more...
- Published
- 2016
48. SYNTHESIS AND SCREENING OF SOME AZOMETHINES BEARING METHYL SALICYLATE MOIETY FOR ANTIBACTERIAL ACTIVITIES
- Author
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Shipra Baluja and Sumitra Chanda
- Subjects
azomethines ,methyl salicylate ,antibacterial activity ,agar disc method ,DMF ,DMSO ,Pharmacy and materia medica ,RS1-441 - Abstract
In this study, the series of novel azomethines were synthesized from methyl salicylate and their structural determination was done by IR, NMR and mass spectral data. The screening of these synthesized compounds were done against some Gram positive and Gram negative bacteria in DMF and DMSO solvents by agar disc method. It is observed that solvent and compound structure both affect the inhibition. DMF is found to be good solvent in the present study. Amongst all studied compounds, JB-4 showed maximum zone of inhibition against most of the studied bacterial strains while compound JB-2 is least effective. Thus, substitution affects inhibition and methyl salicylate moiety with cinnamaldehyde side chain is most effective. Further, virtual screening of these compounds was done to evaluate molecular properties and bioactive scores of these compounds. more...
- Published
- 2016
- Full Text
- View/download PDF
49. Phosphorus containing pyrydoxal azomethines and alkoxyfuropyridines of salt structure.
- Author
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Pudovik, Michael A., Kh. Bagautdinova, Roza., Kibardina, Ludmila K., and Burilov, Alexander R.
- Subjects
- *
PHOSPHORUS , *SALT , *MORNING sickness , *ACIDS - Abstract
The reaction of azomethines of pyridoxal or alkoxyfuropyridines with phosphorus acids produces new salt derivatives. [ABSTRACT FROM AUTHOR]
- Published
- 2019
- Full Text
- View/download PDF
50. On the Influence of the Nature of Non-Bridging Donor Atoms on the Structure and Magnetic Properties of Binuclear Cu(II) Complexes with Heterocyclic Azomethine Ligands.
- Author
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Shcherbakov, I. N., Levchenkov, S. I., Popov, L. D., Tupolova, Yu. P., Morozov, A. N., Raspopova, E. A., and Lyubchenko, S. N.
- Subjects
- *
MAGNETIC structure , *MAGNETIC properties , *SCHIFF bases , *LIGAND exchange reactions , *ATOMS , *COPPER & the environment - Abstract
Binuclear complex [Cu2L(μ2-pz)] (pz = pyrazolate anion) of copper(II) with the condensation product of 1,3-diamino-2-propanol (DAP) and 4-formyl-3-formylcoumarin (H3L) is synthesized and characterized. Magnetic properties of the complex are compared with those demonstrated by a number of previously studied compounds based on bis-azomethine derivatives of DAP with the structure similar to that of studied compounds, i.e. identical exchange fragments and immediate donor environments of copper(II) ions. Antiferromagnetic exchange parameters of these complexes are calculated within the DFT method using the "broken-symmetry" approximation. It is shown for the complexes with the same structure of the exchange fragment and the nearest donor environment of metal centers that the significant variation of the exchange parameter (∼100 cm−1) is determined by the electronic nature of non-bridging donor oxygen atoms of the carbonyl fragment of the bis-azomethine ligand. [ABSTRACT FROM AUTHOR] more...
- Published
- 2019
- Full Text
- View/download PDF
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