In this study, the synthesis of di-[2-(3-alkyl/aryl-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl)-azomethinephenyl] isophtalates (2a-g) from the reactions of 3-alkyl/ aryl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1a-g) with di-(2-formylphenyl) isophtalate is described. Then, the compounds 2 were treated with morpholine in the presence of formaldehyde to synthesize di-{2-[1-(morpholine-4-yl-methyl)-3alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl]-azomethinephenyl} isophtalates (3a-g). The newly synthesized compounds were characterized using IR, 1 H-NMR and 13 C-NMR spectral data. In addition, the compounds synthesized were screened for their antimicrobial activities. Furthermore, the antioxidant properties of the newly synthesized compounds were analysed for their in-vitro potential antioxidant activities in three different methods (reducing power, free radical scavenging and metal chelating activity). These antioxidant activities were compared to those from standard antioxidants, such as BHA, BHT, EDTA and α-tocopherol.

A series of 3-alkyl(aryl)-4-[3-(2-metylbenzoxy)-4-methoxybenzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones (1-9) were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropyl alcohol, tert-butyl alcohol, acetonitrile, and N,N-dimethylformamide (DMF), and graphs were drawn for all cases. The half-neutralization potential values and the corresponding pKa values were determined by the half neutralization method. Thus, the effects of solvents and molecular structure upon acidity were discussed.

In this study, to determine the pKa values of 2-ethoxy-6-(3-substitue-4,5-dihydro-1H-1,2,4-triazol-5-one-4-yl-azomethine)-phenyl benzoates (1-9) were titrated potentiometrically with tetrabutylammonium hydroxide in four non-aqueous solvents such as isopropyl alcohol, tert-butyl alcohol, acetone and N,N-dimethylformamide (DMF), and graphs were drawn for all cases. In addition, the effects of solvents and molecular structure upon acidity compounds 1-9 were also determined and discussed. The half-neutralization potential values and the corresponding pKa values were determined by the half neutralization method.

In this article, 1-(2,6-dimethylmorpholine-4-yl-methyl)-3-methyl-4-[3-ethoxy-(4benzenesulfonyloxy)-benzylidenamino]-4,5-dihydro-1H-1,2,4-triazol-5-one has been theoretically studied. The 1 H and 13 C NMR chemical shifts of the title molecule were calculated by the GIAO method and compared with experimental results. The vibrational frequency values of this compound have been calculated. The polarizability (α), hyperpolarizability (β), dipole moment along with molecular electrostatic potential surface of the title compound have been performed. The molecular electrostatic potential (MEP) map was calculated to assign reactive site on the surface of the molecule. The calculated electronic, structural and thermodynamic parameters of the title molecule were examined by using the density functional method (DFT/B3LYP) with 6-31G(d,p) basis set.

In this study, the effects of solvents and molecular structure upon acidity, five 3-alkyl(aryl)-4-phthalimido-4,5-dihydro-1H-1,2,4-triazol-5-ones (3-7) were potentiometrically titrated with tetrabutylammonium hydroxide (TBAH) in four different anhydrous solvents (isopropyl alcohol, acetonitrile, tert-butyl alcohol and N,N-dimethylformamide) and HNP and corresponding pKa values were determined by half-neutralization method for all cases.

This work was carried out in collaboration between all authors. Author HY designed the study, managed the literature searches and interpreted all spectroscopic and experimental results. Author GK wrote the protocol and performed all theoretical studies. Author GO wrote the first draft of the manuscript and interpreted the theoretical results of the study. All authors read and approved the final manuscript.

No abstract

A series of 2-ethoxy-4-{[3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (3) were synthesized from the reactions of 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1) with 2-ethoxy-4-formyl-phenyl benzenesulfonate (2). N-acetyl derivatives (4) of compounds 3 were also obtained. Then, the compounds 3 have been treated with morpholine and 2,6-dimethylmorpholine in the presence of formaldehyde to synthesize 2-ethoxy-4-{[1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (5) and 2-ethoxy-4-{[1-(2,6-dimethylmorpholine-4-yl-methyl)-3-alkyl(aryl)-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl]-azomethine}-phenyl benzenesulfonates (6), respectively. The structures of twenty-six new compounds were identified by using elemental analysis, IR, 1H NMR, 13C NMR, and MS spectral data. In addition, in vitro antibacterial activities of the new compounds were evaluated against six bacteria such as Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klepsiella pneumonia according to agar well diffusion method. Furthermore, in order to determine the possible antidiabetic properties of the synthesized 1,2,4-triazole derivatives, inhibition effects on the AR enzyme were investigated and molecular docking studies were carried out to determine the receptor-ligand interactions of these compounds. IC50 values of triazole-derived compounds (6a, 6b, 6d-g) against AR enzyme were determined as 0.95 µM, 0.75 µM, 1.83 µM, 0.62 µM, 1.05 µM, 1.06 µM, respectively. Considering the docking scores and binding energies obtained docking studies, it has been shown that molecules fit very well to the active site of the AR enzyme.