Ahmet Cansız

6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: synthesis, experimental, theoretical characterization and biological activities.

The molecular geometry, vibrational frequencies, and gauge including atomic orbital (GIAO) (1)H and (13)C NMR chemical shift values of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional theory (DFT) methods with 6-31G(d) basis sets, and compared with the experimental data. The calculated results show that the optimized geometries can well reproduce the crystal structural parameters and the theoretical vibrational frequencies, and (1)H and (13)C NMR chemical shift values show good agreement with experimental data. To determine conformational flexibility, molecular energy profile of the title compound was obtained by HF/6-31G(d) and (DFT/B3LYP) calculations with respect to selected degree of torsional freedom, which was varied from -180° to +180° in steps of 10°. The energetic behavior of the title compound in solvent media was examined using the B3LYP method with the 6-31G(d) basis set by applying the Onsager and the polarizable continuum model (PCM). The results obtained with these methods reveal that the PCM method provided more stable structure than Onsagers method. The title compound has been tested in vitro for biological effects.

3‐(2‐Furyl)‐4‐(4‐methoxy­phenyl)‐1H‐1,2,4‐triazole‐5(4H)‐thione

The title compound, C13H11N3O2S, has a non-planar conformation. The dihedral angles are 3.41 (8) and 85.48 (7)° between the triazole ring plane and the furan and benzene ring planes, respectively. The crystal packing is stabilized by several hydrogen bonds.

6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole

The title compound, C(14)H(9)N(5)S, has been synthesized and characterized both spectroscopically and structurally. The triazolo-thiadiazole system, the pyridine ring and the phenyl ring are all planar. The plane of the triazolo-thiadiazole system forms dihedral angles of 1.53 (13) and 7.55 (12) degrees with the planes of the pyridine and phenyl rings, respectively. In the molecule, there are two intramolecular interactions of types C-H...N and C-H...S. Intermolecular C-H...N interactions involving a phenyl CH group and a triazole N atom lead to the formation of a one-dimensional chain. In the crystal structure, two types of pi-pi interactions affect the packing of the molecules. In addition, there are intermolecular non-bonded S...N contacts of 2.870 (2) A, which may cause steric hindrance.

4-Allyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione: synthesis, experimental and theoretical characterization.

The title molecule, 4-allyl-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione (C(10)H(10)N(4)S), was synthesized and characterized by IR-NMR spectroscopy and single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group is P2(1)/c, a=8.006(5)Å, b=15.363(5)Å, c=8.936(5)Å, β=104.441(5)° and V=1064.4(10)Å(3), F(000)=456, D(x)=1.362 g/cm(3). In addition to the molecular geometry from X-ray experiment, the molecular geometry, vibrational frequencies, gauge including atomic orbital (GIAO) (1)H and (13)C chemical shift values of the title compound in the ground state have been calculated using the Hartree-Fock (HF) and density functional method (DFT/B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of the title compound was obtained by HF/6-31G(d) and (DFT/B3LYP) calculations with respect to selected degree of torsional freedom, which was varied from -180° to +180° in steps of 10°. Besides, molecular electrostatic potential (MEP), frontier molecular orbitals (FMO), and several thermodynamic properties were performed by the HF and DFT methods.

4‐Ethyl‐5‐(2‐hydroxy­phenyl)‐2H‐1,2,4‐triazole‐3(4H)‐thione

In the title compound, C10H11N3OS, an intramolecular C—H⋯S hydrogen bond is observed, which leads to a thione tautomer in the solid state. The benzene ring forms a dihedral angle of 85.33 (6)° with the triazole ring. There are intermolecular N—H⋯S and O—H⋯N hydrogen bonds and C—H⋯π interactions.

Synthesis of (1R,2R)-1,2-bis-(5-(4-hydroxynaphthalen-1-ylazo)-[1,3,4]thiadiazol-2-yl)-ethane-1,2-diol

In this study, (1R,2R)-1,2-bis-(5-amino-1,3,4-thiadiazol-2-yl)ethane-1,2-diol (2), was synthesized by using (2R,3R)-(+)-Tartaric acid (1) as starting compound. Then the diazo component 3 was obtained from 2 and 1-naphthol. In addition, the structures of the synthesized compounds 2 and 3 were confirmed by elemental analyses, IR, 1H-NMR, and 13C-NMR spectra.

[Synthesis of two new acetanilide derivatives and their effect on the serum antioxidant vitamins (A, E, and C) and the MDA level in rats].

Acetanilide derivatives, 2,2′-thiobis[N-(4-nitrophenyl)acetamide] and 2,2′-thiobis[N-(4-chlorophenyl)acetamide], were synthesized and characterized. They were shown to cause a considerable oxidative stress in rats.

Synthesis and biological activity of new 2-amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]thiazole derivatives

Abstract2-Amino-4-[3-methyl-3-(5,6,7,8-tetrahydro-2-naphthyl)cyclobutyl]thiazole was synthesized by reaction of 1-methyl-1-(5,6,7,8-tetrahydro-2-naphthyl)-3-chloroacetylcyclobutane with thiourea in ethanol, and its subsequent transformations afforded new derivatives which were tested in vitro for antibacterial activity against some bacteria using the disk diffusion technique.

5-Benzyl-4-phenyl-2,4-di­hydro-1,2,4-triazole-3-thione

As part of structural studies of 1,2,4-triazole derivatives, the crystal structure of the title compound, C15H13N3S, has been investigated. The structure shows a V-shape in the molecular skeleton, as found for similar compounds. The crystal structure is stabilized by an N—H⋯S and three C—H⋯π intermolecular interactions.

3‐Benzyl‐4‐(4‐methyl­phenyl)‐1H‐1,2,4‐triazole‐5(4H)‐thione

The title compound, C16H15N3S, displays the usual geometrical parameters of 1,2,4-triazole derivatives. The occurrence of N—H⋯S hydrogen-bonding interactions results in the formation of dimers.