Design, structural and spectroscopic elucidation, and the in vitro biological activities of new diorganotin dithiocarbamates

• DOI: 10.1016/j.ejmech.2012.10.021
• Publication Date: 2012-10-24T16:00:17Z
• Authors: Isabella P. Ferreira; Geraldo M. de Lima; Eucler B. Paniago; Willian R. Rocha; Jacqueline A. Tak...; Carlos B. Pinheiro; José D. Ardisson
• Keywords: Models, Molecular; Magnetic Resonance Spectroscopy; Bacteria; Dose-Response Relationship, Drug; Molecular Structure; Fungi; Microbial Sensitivity Tests; Crystallography, X-Ray; 01 natural sciences; 3. Good health; 0104 chemical sciences; Structure-Activity Relationship; Anti-Infective Agents; Thiocarbamates; Drug Design; Organotin Compounds

The reaction of 2,2-dimethoxy-N-methylethyllamine or 2-methyl-1,3-dioxolane with CS(2) in alkaline media produced two novel dithiocarbamate salts. Subsequent reactions with organotin halides yielded six new complexes: [SnMe(2){S(2)CNR(R(1))(2)}(2)] (1), [Sn(n-Bu)(2){S(2)CNR(R(1))(2)}(2)] (2), [SnPh(2){S(2)CNR(R(1))(2)}(2)] (3), [SnMe(2){S(2)CNR(R(2))(2)}(2)] (4), [Sn(n-Bu)(2){S(2)CNR(R(2))(2)}(2)] (5), [SnPh(2){S(2)CNR(R(2))(2)}(2)] (6), where R = methyl, R(1) = CH(2)CH(OMe)(2), and R(2) = 2-methyl-1,3-dioxolane. All compounds were identified in terms of infrared, (1)H and (13)C NMR, and the complexes were also characterized using (119)Sn NMR, (119)Sn Mössbauer and X-ray crystallography. The biological activity of all derivatives has been screened in terms of IC(90) and IC(50) against Aspergillus flavus, Aspergillus niger, Aspergillus parasiticus, Penicillium citrinum, Curvularia senegalensis, Staphylococcus aureus, Listeria monocytogenes, Bacillus cereus, Streptococcus sanguinis, Escherichia coli, Citrobacter freundii, Salmonella typhimurium, and Pseudomonas aeruginosa and the results correlated well with a performed study of structure-activity relationship (SAR). Complexes (3), (5) and (6) displayed the best IC(90) and IC(50) in the presence of the fungi, greater than that of miconazole, used as control drug.