1,2,4-triazole derivative with Schiff base; thiol-thione tautomerism, DFT study and antileishmanial activity

Süleymanoğlu, Nevin; Ustabaş, Reşat; Direkel, Şahin; Alpaslan, Yelda Bingöl; Ünver, Yasemin

doi:10.1016/j.molstruc.2017.08.075

Cited by 47 publications

(23 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…We concluded that the infrared spectra of the synthesized product conformed to the molecular conformation of 4-amino-1,2, 4-triazole-nisopropyl butylamine. 1 H NMR spectrum 13C NMR spectrum Figure 4 shows the seven types of carbon in the final product: one on the triazine rings, four on the benzene rings, one on -C¼N, and one on the triazole rings. In Figure 4, 172.779 ppm was the signal peak of carbon on the triazine rings, 153.987-157.050 ppm indicated the carbon on -C¼N, 38.909-40.156 ppm indicated the carbon on the benzene rings, and 122.310-138.875 ppm indicated the carbon on the triazole rings, which was in accord with the basic law of chemical shift of aromatic ring carbon.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Preparation and antitumor effects of 4-amino-1,2,4-triazole Schiff base derivative

et al. 2020

View full text Add to dashboard Cite

Objectives: The purpose of this paper was to synthesize 4-amino-1,2,4-triazole Schiff base derivative and to evaluate its antitumor activity. Methods: 2,4,6-Tris (4-formylphenoxy)-1,3,5-triazine was synthesized by nucleophilic substitution with reaction of p-hydroxybenzaldehyde with cyanuric chloride. Then, the intermediate was reacted with 1,2,4-triazole to form 4-amino-1,2,4-triazole Schiff base derivative by reduction and ammonification of aldehydes. The 4-amino-1,2,4-triazole Schiff base derivative was characterized by infrared spectroscopy, nuclear magnetic resonance, and elemental analyses. Finally, the anticancer effect of 4-amino-1,2,4-triazole Schiff base derivative was evaluated by MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay on a lung adenocarcinoma cell line (A549) and a human hepatoma cell line (Bel7402). Results: The product synthesized in this study was confirmed to be 4-amino-1,2,4-triazole Schiff base derivative, and it significantly suppressed the proliferation of cancer cell lines in a dosedependent manner. Conclusions: We successfully prepared 4-amino-1,2,4-triazole Schiff base derivative and verified its antitumor activity.

show abstract

Section: Resultsmentioning

confidence: 99%

“…After pressing the mixture, the product was characterized by infrared spectroscopy, 1 H nuclear magnetic resonance (NMR), and 13C NMR. 1 H NMR and 13 C NMR were performed using deuterium instead of dimethyl sulfoxide (DMSO) as solvent.…”

Section: Equipment and Reagentsmentioning

confidence: 99%

Preparation and antitumor effects of 4-amino-1,2,4-triazole Schiff base derivative

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Schiff base derivatives are useful compounds that have many applications. They have been playing vital roles in the pharmaceutical industry as antimicrobials, antidepressants, cytotoxics, analgesics, antileischmanials, anticonvulsants and fungicides and as anti‐inflammatory and anticancer agents . In coordination chemistry, Schiff bases constitute privileged ligands that can form stable complexes with transition metals .…”

Section: Introductionmentioning

confidence: 99%

New copper(II) and zinc(II) complexes based on azo Schiff base ligand: Synthesis, crystal structure, photoisomerization study and antibacterial activity

Slassi

El‐Ghayoury

Aarjane

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

Newly synthesized mononuclear copper(II) and zinc(II) complexes containing an azo Schiff base ligand (L), prepared by condensation of 2‐hydroxy‐5‐(o‐tolyldiazenyl)benzaldehyde and propylamine, were obtained and then characterized using infrared and NMR spectroscopies, mass spectrometry and X‐ray diffraction. Ligand L behaves as a bidentate chelate by coordinating through deprotonated phenolic oxygen and azomethine nitrogen. The copper and zinc complexes crystallize in triclinic and orthorhombic systems, respectively, with space groups P−1 and Pca21. In these complexes, the Cu(II) ion is in a square planar geometry while the Zn(II) ion is in a distorted tetrahedral environment. The photochemical behaviors of ligand L, [Cu(L)2] and [Zn(L)2] were investigated. The azo group in L underwent reversible trans–cis isomerization under UV and visible irradiation. This process was inhibited for the complexes. In addition, ligand L and its copper and zinc complexes were assessed for their in vitro antibacterial activities against four pathogenic strains.

show abstract

“…activity can be obtained . Given the excellent antifungal, antibacterial, anticancer, antimalarial, and cytotoxic activities of 1,2,4‐triazole Schiff base derivatives, as well as their other excellent properties, the synthesis routes and biological properties of these compounds have attracted extensive attention.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

et al. 2020

ChemistrySelect

View full text Add to dashboard Cite

Seven Schiff base compounds were synthesized via the nucleophilic condensation of 5‐substituted‐3‐thione‐1,2,4‐triazole and 2,4,6‐trimethyl benzaldehyde. All of the synthesized compounds (A1–A3 and B1–B4) were thoroughly characterized by using spectroscopic and physical analytical methods. The in vitro antifungal activities of the prepared compounds were studied, and results showed that A2, B1, B2, and B3 have good biological activity. Molecular docking was used to predict the binding modes of the ligands to 6CR2 protein, and the reasons behind the excellent activities of A2 and B2 were explored. Finally,the highest occupied molecular orbital, lowest unoccupied molecular orbital, and natural bonding orbital of the compounds were calculated by using density functional theory at the B3LYP/6‐31G level.

show abstract

1,2,4-triazole derivative with Schiff base; thiol-thione tautomerism, DFT study and antileishmanial activity

Cited by 47 publications

References 28 publications

Preparation and antitumor effects of 4-amino-1,2,4-triazole Schiff base derivative

Preparation and antitumor effects of 4-amino-1,2,4-triazole Schiff base derivative

New copper(II) and zinc(II) complexes based on azo Schiff base ligand: Synthesis, crystal structure, photoisomerization study and antibacterial activity

Synthesis, Biological Activity, and Molecular Docking Studies of Novel 5‐Substituted‐1,2,4‐Triazole‐3‐thione Derivatives

Contact Info

Product

Resources

About