•Compounds 2F, 3F and 4F were synthesized.•The compounds were characterized by IR, 1H NMR, 13C NMR spectra.•Theoretical study for compounds 2F-4F was performed by using DFT/B3LYP/6–311++G(d,p) ...method.•Newly synthesized compounds (2F-4F) were tested against eight bacteria and two yeast strains.•Compounds 2F-4F were tested for both cancer cells and normal cells.•Molecular docking calculations were performed.
(E)-5-(4-fluorobenzyl)-4-((2-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (2F), (E)-5-(4-fluorobenzyl)-4-((3-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (3F) and (E)-5-(4-fluorobenzyl)-4-((4-fluorobenzylidene)amino)-2,4-dihydro-3H-1,2,4-triazol-3-one (4F) were synthesized and confirmed by FT-IR and 1H, 13CNMR spectroscopic methods. Theoretical study for compounds 2F-4F was performed by using DFT/B3LYP/6–311++G(d,p) method. The optimized structures, IR and NMR data, the frontier molecular orbitals (HOMO and LUMO) and the molecular electrostatic potential (MEP) map of compounds 2F-4F were calculated. In addition, newly synthesized compounds (2F-4F) were tested against eight bacteria and two yeast strains and their the minimum inhibitory concentration (MIC) values were determined. The MTT test was performed to measure the antiproliferative effects of the 2F-4F compounds on cell proliferation (NCI-60 screening methodology). Molecular docking calculations were performed to investigate ligand-protein interactions between the compounds (2F and 3F) and the Epidermal Growth Factor Receptor (EGFR) and the Vascular Endothelial Growth Factor Receptor (VEGFR1).
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•Synthesis of new peripherally cobalt(II), manganese(III) phthalocyanines.•Synthesis of new non-peripherally cobalt(II), manganese(III) phthalocyanines.•Investigation of ...electrochemical properties.
In this study, 4-2-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)ethoxyphthalonitrile ET-CN, 3-2-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)ethoxyphthalonitrile n-ET-CN and cobalt(II), manganese(III) phthalocyanines bearing 2-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)ethoxy group at peripheral, non-peripheral positions were synthesized for the first time. The new compounds have been characterized by FT-IR, NMR (only for ET-CN, n-ET-CN), mass and UV-Vis spectroscopy (except ET-CN, n-ET-CN) techniques. Electrochemistry of cobalt(II), manganese(III) phthalocyanines bearing 2-(3,5-diphenyl-1H-1,2,4-triazol-1-yl)ethoxy group at peripheral, non-peripheral positions were examined by using cyclic voltammetry.
Phthalimidoacetyl isothiocyanate underwent addition-cyclization reactions with some nitrogen and carbon nucleophilic reagents. Simultaneous or subsequent cyclization of the obtained adducts gave ...target heterocyclic systems such as 1,2,4-triazoles, 1,3-diazines, 1,3-oxazines and thiourea attached to a phthalimido moiety. The antimicrobial activity of the synthesized compounds was tested.
In this study, triazol derivatives, 4,4'-(((1E, 1E')-1,2-phenylenebis (methanylyidene)) bis (azanylidene)) bis (5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (2), 4,4'-(((1E, 1E')-1,3-phenylenebis ...(methanylyidene)) bis (azanylidene)) bis (5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (3) and 4,4'-(((1E, 1E')-1,4-phenylene bis (methanyl yidene)) bis (azanylidene)) bis (5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (4) were synthesized from the reaction of 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one and phthalaldehyde/isophthalaldehyde/terephthalaldehyde, respectively. Compounds 2-4 were characterized by Fourier transform infrared (FTIR), proton and carbon-13 nuclear magnetic resonance (
1
H- and
13
C- NMR) spectroscopic methods. Theoretical study for compounds 2-4 were carried out by DFT/B3LYP/6-311++G(d,p). Structural and spectroscopic parameters were determined theoreticaly and compared with experimental ones. Also, the molecular electrostatic potential (MEP) maps of compounds were obtained. Leishmanicidal activity of compounds 2-4 against to Leishmania infantum was determined by microdilution broth method containing alamar blue. As a result of the study, compounds 2-4 were found to be effective against the specie of Leishmania. Molecular docking analysis against Trypanothione Reductase (TRe) with compound 2 was carried out to see the necessary interactions responsible for antileishmanial activity. The docking calculations of compound 2 supported the antileishmanial activity exhibiting high inhibition constant.
Communicated by Ramaswamy H. Sarma
The blue-light-emitting Ir(III) complexes using 2-(3-(trifluoromethyl) -1H-1,2,4-triazol-5-yl)pyridine and fluorinated 2-phenylpyridine as ligands were synthesized and characterized in details. Their ...molecular structures were confirmed by 1H NMR, FT-IR and elemental analyzer. The emission peaks of complex (F2,4ppy)2Ir(tfmptz) using 2-(2,4-difluorophenyl)pyridine as main ligand are located at 457 and 481 nm. Increasing the number of F atoms leads to a lower the lowest unoccupied molecular orbital energy level. Phosphorescent organic light-emitting devices doped the synthesized Ir(III) complexes into 4,4′-N,N′-dicarbazolebiphenyl as emitting layers were fabricated. The based-(F3,4,5ppy)2Ir(tfmptz) device shows the maximum current efficiency of 9.9 cd/A with the electroluminescent peaks at 471 and 502 nm.
Two blue-emitting Ir(III) complexes using 2-(3, 4, 5-trifluorophenyl)pyridine (F3,4,5 ppy) and 2-(2, 4-difluorophenyl)pyridine (F2,4ppy) as main ligands have been reported and their photophysical properties have been investigated. The (F2,4ppy)2Ir(tfmptz)-based devices have the superior performances with the current efficiency of 5.2 cd/A. Display omitted
A new class of 2-amino-4-(1,2,4-triazol)pyridine derivatives were designed and synthesized as potent epidermal growth factor receptor inhibitors. In particular, compound 10c exhibited significant ...inhibitory against EGFRL858R/T790M, and also displayed potent anti-proliferative activity against non-small cell lung cancer cell line H1975. Besides, compound 10j showed potent inhibitory activity against glioblastoma cell line U87-EGFRvⅢ, which was at least 3-fold more potent than Osimertinib and 25-fold superior to Lazertinib. Moreover, molecular modeling and molecular dynamics simulations disclosed the binding model of the most active compound to the domain of EGFR. This contribution provides 2-amino-4-(1,2,4-triazol)pyridines as a new scaffold for EGFRT790M and/or EGFRvⅢ inhibitor.
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•Sixteen 2-amino-4-(1,2,4-triazol)pyridine derivatives were designed and synthesized.•Compound 10c exhibited strong inhibitory activities against EGFRL858R/T790M enzyme.•Compound 10j showed potent inhibitory activity against U87-EGFRvIII cell.•Molecular docking and molecular dynamics simulation gave a probable explanation for the activity of 10c.
Current trends in the search for new biologically active compounds among synthetic molecules have arguably proved a priority in studies of the heterocyclic 1,2,4-triazole system. For many years, ...1,2,4-triazole derivatives remain the object of close attention of scientists of various scientific fields. The unique properties of 1,2,4-triazole derivatives include high reactivity, which allows different modification of this system, practical absence of toxicity of these derivatives and the presence of a wide range of biological, pharmacological properties, which in the complex provides the prerequisites for the creation of new biologically active compounds, and in the future, active pharmaceutical ingredients (AFI). The aim of our work is to investigate some transformations in a number of derivatives of 5-(thiophen-3-ylmethyl) -4-R1-1,2,4-triazole-3-thiol, to study the physicochemical properties of the new synthesized compounds. A well-known fact remains the successful attempt of many scientists involved in the study of the heterocyclic 1,2,4-triazole system to synthesize potential biologically active compounds. The process of creating new molecules is very painstaking and requires considerable effort. The chemical approaches for the synthesis of the starting compounds required for further transformations are well known and described. Therefore, we used the corresponding N-R1-2 as intermediates for the synthesis of new 5-(thiophen-3-ylmethyl) -4-R1-1,2,4-triazole-3-thiols appropriate ones were used N-R1-2-(2-(thiophen-3-yl) acetyl) hydrazinocarbothioamide.
The derivatives of 1,2,4-triazole are of the great scientific interest in the fields of pharmaceutics, agricultural chemistry, and construction The production of Trifuzol-Neo has already been ...launched, and it is now commercially available. Compounds based on 1,2,4-triazole may also be useful in veterinary practice due to their antiviral activity. Trifuzol-Neo, or piperidinium (5-(2-furanyl)-4-phenyl-4Н-1,2,4-triazol-3-ylthio)acetate (Figure 1), has already proved to be an effective immunostimulator for poultry.Since that, the quality control of raw materials and the ready product is required during the production stage. Currently, there is only one method for determination of the assay of Trifuzol-Neo, which involves HPLC-DMD (Center of Medical Research Information and Patent and Licensing Practice of Ukraine. The main disadvantages of HPLC-DMD are the use of relatively high amounts of costly solvents (acetonitrile in this case), considerable baseline instability, and time-consuming system stabilization. Gas-chromatography is able to avoid these constrictions since it involves gas as a mobile phase, which is a more cost-effective and reproducible alternative. The newly developed GC/MS method for Trifuzol-Neo assay determination consists of the following steps: weighing 20.0mg of Trifuzol-Neo powder, dillution in 20mL methanol, injection of 0.5uL of the obtained solution to GC column (at least three times). The same operations are done with a Trifuzol-Neo standard.
Treatment of
4
N-monosubstituted bis(thiosemicarbazone) ligands of 3,5-diacetyl-1,2,4-triazol series with lithium tetrachloridopalladate gave the dinuclear complexes of general formula Pd(μ-H
3L
1–5)
...2, but using dichloridobistriphenylphosphinepalladium(II) salt, the first mononuclear bis(thiosemicarbazone)–palladium–triphenylphosphine complexes of the 3,5-diacetyl-1,2,4-triazol series, Pd(H
3L
1–5)PPh
3, have been obtained. All the compounds have been characterized by elemental analysis and by IR and NMR spectroscopy, and the crystal and molecular structures of dinuclear complexes Pd(μ-H
3L
3)
2 and Pd(μ-H
3L
5)
2 as well as mononuclear complexes Pd(H
3L
1)PPh
3, Pd(H
3L
2)PPh
3, Pd(H
3L
3)PPh
3 and Pd(H
3L
4)PPh
3 have been determined by X-ray crystallography. The new compounds synthesized have been evaluated for antiproliferative activity
in vitro against NCI-H460, A2780 and A2780cisR human cancer cell lines. Subsequent toxicity study, on normal renal LLC-PK1 cells, shows that all compounds investigated exhibit very low toxicity on kidney cells with respect to cisplatin.
New mononuclear and dinuclear palladium(II) complexes derived from
N
4-substituted bis(thiosemicarbazone) ligands have been synthesized and characterized. They exhibit important antitumour activity since they are capable of circumvent cisplatin resistance in A2780cisR cells and reducing toxicity on normal kidney cells.
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