Design, structural and spectroscopic elucidation, and the in vitro biological activities of new diorganotin dithiocarbamates
| Autor: | Jacqueline A. Takahashi, Isabella P. Ferreira, Carlos B. Pinheiro, José D. Ardisson, Willian R. Rocha, Eucler B. Paniago, Geraldo M. de Lima |
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| Rok vydání: | 2012 |
| Předmět: |
Models
Molecular Magnetic Resonance Spectroscopy Stereochemistry Aspergillus flavus Microbial Sensitivity Tests Crystallography X-Ray Structure-Activity Relationship chemistry.chemical_compound Anti-Infective Agents Thiocarbamates Drug Discovery Organotin Compounds Penicillium citrinum Dithiocarbamate Pharmacology chemistry.chemical_classification Bacteria Dose-Response Relationship Drug Molecular Structure biology Organic Chemistry Aspergillus niger Fungi General Medicine Nuclear magnetic resonance spectroscopy Carbon-13 NMR biology.organism_classification Aspergillus parasiticus Citrobacter freundii chemistry Drug Design |
| Zdroj: | European Journal of Medicinal Chemistry. 58:493-503 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2012.10.021 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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