title: A novel series of thiosemicarbazone drugs: from synthesis to structure.
abstract: A new series of thiosemicarbazones (TSCs) and their 1,3,4-thiadiazolines (TDZs) containing acetamide group have been synthesized from thiosemicarbazide compounds by the reaction of TSCs with cyclic ketones as well as aromatic aldehydes. The structures of newly synthesized 1,3,4-thiadiazole derivatives obtained by heterocyclization of the TSCs with acetic anhydride were experimentally characterized by spectral methods using IR, (1)H NMR, (13)C NMR and mass spectroscopic methods. Furthermore, the structural, thermodynamic, and electronic properties of the studied compounds were also studied theoretically by performing Density Functional Theory (DFT) to access reliable results to the experimental values. The molecular geometry, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and Mulliken atomic charges of the studied compounds have been calculated at the B3LYP method and standard 6-31+G(d,p) basis set starting from optimized geometry. The theoretical (13)C chemical shift results were also calculated using the gauge independent atomic orbital (GIAO) approach and their respective linear correlations were obtained.
authors.affiliation: Department of Biochemistry and National Magnetic Resonance Facility at Madison (NMRFAM), University of Wisconsin-Madison, Madison, WI 53706, USA.
authors.forename: Hossein Pasha
authors.initials: HP
authors.lastname: Ebrahimi
authors.affiliation: Department of Chemistry, College of Education for Pure Science, University of Basrah, Basrah, Iraq. Electronic address: jshalkabi2@gmail.com.
authors.forename: Jabbar S
authors.initials: JS
authors.lastname: Hadi
authors.affiliation: Department of Chemistry, College of Education for Pure Science, University of Basrah, Basrah, Iraq. Electronic address: tahseen.alsalim@uobasrah.edu.iq.
authors.forename: Tahseen A
authors.initials: TA
authors.lastname: Alsalim
authors.affiliation: Department of Chemistry, College of Education for Pure Science, University of Basrah, Basrah, Iraq.
authors.forename: Thaer S
authors.initials: TS
authors.lastname: Ghali
authors.affiliation: David Geffen School of Medicine, University of California at Los Angeles, Los Angeles, CA 90095, USA.
authors.forename: Zeinab
authors.initials: Z
authors.lastname: Bolandnazar
mesh_terms: D008958:Models, Molecular; D015394:Molecular Structure; D013057:Spectrum Analysis / Q000379:methods; D013882:Thiosemicarbazones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D013882:Thiosemicarbazones
keywords: DFT computational studies; Sulfa drug; Thiadiazole; Thiadiazoline; Thiosemicarbazide; Thiosemicarbazone