ABSTRACT
Two new molecular structures, namely 1,3-bis(trimethylsilyl)-1H-benzimidazole-2(3H)-thione, C13H22N2SSi2, (2), and 1-trimethylsilyl-1H-benzimidazole-2(3H)-thione, C10H14N2SSi, (3), are reported. Both systems were derived from 1H-benzimidazole-2(3H)-thione. Noncovalent C-H···π interactions between the centroid of the benzmidazole system and the SiMe3 groups form helicoidal arrangements in (2). Dimerization of (3) results in the formation of R2(2)(8) rings via N-H···S interactions, along with parallel π-π interactions between imidazole and benzene rings.
Subject(s)
Benzimidazoles/chemistry , Silanes/chemistry , Thiones/chemistry , Crystallography, X-Ray , Hydrogen Bonding , Molecular StructureABSTRACT
Coordination compounds with cobalt(II), nickel(II), copper(II) and zinc(II) and the ligand 2,6-bis(2,6-diethylphenyliminomethyl)pyridine (L) were synthesized and fully characterized by IR and UV-Vis-NIR spectroscopy, elemental analysis, magnetic susceptibility and X-ray diffraction for two representative cases. These novel compounds were designed to study their activity as anti-proliferative drugs against different human cancer cell lines. The tridentate ligand forms heptacoordinated compounds from nitrate metallic salts, where the nitrate acts in a chelating form to complete the seven coordination positions. In vitro cell growth inhibition was measured for Co(II), Cu(II) and Zn(II) complexes, as well as for the free ligand. Upon coordination, the IC50 value of the transition-metal compounds is improved compared to the free ligand. The copper(II) and zinc(II) compounds are the most promising candidates for further in vitro and in vivo studies. The activity against colon and prostate cell lines merits further research, in views of the limited therapeutic options for such cancer types.
Subject(s)
Antineoplastic Agents/chemistry , Coordination Complexes/chemistry , Coordination Complexes/toxicity , Pyridines/chemistry , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/toxicity , Cell Line, Tumor , Cobalt/chemistry , Coordination Complexes/chemical synthesis , Copper/chemistry , Crystallography, X-Ray , Humans , Ligands , Magnetic Resonance Spectroscopy , Models, Molecular , Nickel/chemistry , Spectroscopy, Near-Infrared , X-Ray Diffraction , Zinc/chemistryABSTRACT
Herein we report the synthesis, structural and spectroscopic characterization of coordination compounds with bis[2-(1H-benzimidazol-2-yl)phenyl]disulfide [bis-(2phSbz)] (1) and cobalt(II), zinc(II) and cadmium(II) halides (2-7). Their X-ray diffraction analyses showed that the metal ions present similar distorted tetrahedral structures, with the disulfide ligand coordinated through the imidazolic nitrogen atoms, forming a twisted eleven membered chelate ring. Structures of nickel(II) compounds 8 and 9, showed that the disulfide bond in the ligand was cleaved forming six membered chelates. In 8, the two ligands are sulfides, however in 9 one of them was oxidized to a sulfone. In both compounds the nickel(II) has a distorted square planar geometry and the sulfur atoms are in cis positions. The oxidation reaction of bis-(2phSbz) was performed in KMnO4/NaOH, giving the 2-(1H,3H-benzimidazolium-2-yl)-benzene sulfonate (10). The solid state structure of compounds 2-5 and 7-10 was determined by X-ray diffraction analyses.
Subject(s)
Benzimidazoles/chemistry , Chelating Agents/chemistry , Coordination Complexes/chemistry , Disulfides/chemistry , Halogens/chemistry , Metals/chemistry , Cadmium/chemistry , Cobalt/chemistry , Coordination Complexes/chemical synthesis , Crystallography, X-Ray , Molecular Conformation , Nickel/chemistry , Zinc/chemistryABSTRACT
A new sulfate acid polymorph of 1,3-dihydrobenzotriazole, viz. 1,3-dihydrobenzotriazolium hydrogensulfate, C(6)H(6)N(3)+.HSO4-, differs from an existing polymorph in that the polymeric interaction between the HSO4- anions, together with different classical (D-H...A) and nonclassical (C-H...A) interactions, changes the space group.