title: 6-Phenyl-3-(4-pyridyl)-1,2,4-triazolo-[3,4-b][1,3,4]thiadiazole: synthesis, experimental, theoretical characterization and biological activities.
abstract: 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 Onsager's method. The title compound has been tested in vitro for biological effects.
authors.affiliation: Firat University, Faculty of Science, Department of Chemistry, 23119 Elazığ, Turkey.
authors.forename: Ahmet
authors.initials: A
authors.lastname: Cansız
authors.forename: Ahmet
authors.initials: A
authors.lastname: Cetin
authors.forename: Cahit
authors.initials: C
authors.lastname: Orek
authors.forename: Mustafa
authors.initials: M
authors.lastname: Karatepe
authors.forename: Kamiran
authors.initials: K
authors.lastname: Sarac
authors.forename: Alper
authors.initials: A
authors.lastname: Kus
authors.forename: Pelin
authors.initials: P
authors.lastname: Koparir
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001713:Biphenyl Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D016166:Free Radical Scavengers / Q000494:pharmacology; D006860:Hydrogen Bonding; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010851:Picrates / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D012997:Solvents / Q000737:chemistry; D055672:Static Electricity; D013816:Thermodynamics; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D054159:Torsion, Mechanical; D014732:Vibration
chemical_list: C578296:6-phenyl-3-(4-pyridyl)-1,2,4-triazolo-(3,4-b)(1,3,4)thiadiazole; D000890:Anti-Infective Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D010851:Picrates; D011725:Pyridines; D012997:Solvents; D013830:Thiadiazoles; C004931:1,1-diphenyl-2-picrylhydrazyl