Synthesis, Characterization and In Vitro Antibacterial Studies of Organotin(IV) Complexes with 2-Hydroxyacetophenone-2-methylphenylthiosemicarbazone ( )
Five new organotin(IV) complexes of 2-hydroxyacetophenone-2-methylphenylthiosemicarbazone [H2dampt, (1)] with formula [ (dampt)] (where , (2); , (3); , (4); 2, (5); 2, (6)) have been synthesized by direct reaction of H2dampt (1) with organotin(IV) chloride(s) in absolute methanol. The ligand (1) and its organotin(IV) complexes (2–6) were characterized by CHN analyses, molar conductivity, UV-Vis, FT-IR, 1H, 13C, and 119Sn NMR spectral studies. H2dampt (1) is newly synthesized and has been structurally characterized by X-ray crystallography. Spectroscopic data suggested that H2dampt (1) is coordinated to the tin(IV) atom through the thiolate-S, azomethine-N, and phenoxide-O atoms; the coordination number of tin is five. The in vitro antibacterial activity has been evaluated against Staphylococcus aureus, Enterobacter aerogenes, Escherichia coli, and Salmonella typhi. The screening results have shown that the organotin(IV) complexes (2–6) have better antibacterial activities and have potential as drugs. Furthermore, it has been shown that diphenyltin(IV) derivative (6) exhibits significantly better activity than the other organotin(IV) derivatives (2–5). 1. Introduction Thiosemicarbazones and their metal complexes have received considerable attention in chemistry and biology, primarily because of their marked and various biological properties [1–3]. The pharmacological profiles of 2-formyl, 2-acetyl, and 2-benzoylpyridine thiosemicarbazones have been investigated [4]. Seena and Kurup [5] have synthesized and characterized dioxomolybdenum(IV) complexes with 2-hydroxyacetophenone-N(4)-cyclohexyl and N(4)-phenyl thiosemicarbazone which suggested that the Mo(IV) complex is pentacoordinated [5]. For the past few years, studies of the coordination chemistry of thiosemicarbazone involved complexes with transition metal ions [6–8]. Organotin(IV) complexes have been the subject of interest for some time because of their biomedical and commercial applications including in vitro and in vivo antitumor activity [9, 10]. Many organotin(IV) complexes have been found to be as effective as or even better than traditional anticancer drugs [11–14]. Organotin(IV) chelates with nitrogen, sulfur, and oxygen donor ligands have gained attention during the last few years [15]. The coordination chemistry of tin is extensive with various geometries and coordination numbers known for both inorganic and organometallic complexes [16, 17]. In our previous work, we have reported some new organotin(IV) complexes with heterocyclic-N(4)-cyclohexylthiosemicarbazone ligands [18, 19]. The
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