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

Abstract

The reaction of 2,2-dimethoxy-N-methylethyllamine or 2-methyl-1,3-dioxolane with CS2 in alkaline media produced two novel dithiocarbamate salts. Subsequent reactions with organotin halides yielded six new complexes: [SnMe2{S2CNR(R1)2}2] (1), [Sn(n-Bu)2{S2CNR(R1)2}2] (2), [SnPh2{S2CNR(R1)2}2] (3), [SnMe2{S2CNR(R2)2}2] (4), [Sn(n-Bu)2{S2CNR(R2)2}2] (5), [SnPh2{S2CNR(R2)2}2] (6), where R = methyl, R1 = CH2CH(OMe)2, and R2 = 2-methyl-1,3-dioxolane. All compounds were identified in terms of infrared, 1H and 13C NMR, and the complexes were also characterized using 119Sn NMR, 119Sn Mössbauer and X-ray crystallography. The biological activity of all derivatives has been screened in terms of IC90 and IC50 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 IC90 and IC50 in the presence of the fungi, greater than that of miconazole, used as control drug.