Synthesis, Characterization and Biological Activities of Organotin (IV) Methylcyclohexyldithiocarbamate Compounds

Abstract

Problem statement: The growing interest in the chemistry of sulphur donor ligands are due to their encouraging anticancer, antibacterial and antifungal activities as well as their widespread industrial application. Dithiocarbamates belong to this class and much attention has been paid to them. Approach: Novel organotin compounds with the molecular formula R_mSn[S₂CN(CH₃)(C₆H₁₁)]_4-m (where m = 2, R = CH₃, C₂H₅; m = 3, R = C₆H₅) have been synthesized using in situ method. These compounds were characterized by elemental analysis, IR, ¹H and ¹³C NMR spectroscopy. Results: Elemental analysis revealed that all compounds were of good purity. Infrared spectra of the compounds showed that the thioureide ν(C-N) band was in the region 1450-1500 cm⁻¹. The unsplitting band of ν(C-S) in the region 974-979 cm⁻¹ indicated the bidentate nature of the chelated dithiocarbamato legends. The 13C NMR chemical shift of the carbon atom in the N-CS₂ group appeared in the range of 196.29-199.82 ppm. Single crystal analysis from one of these compounds showed that the chelating mode of the dithiocarbamate groups was isobidentate. These compounds have been screened for antibacterial activity against four bacteria; Staphylococcus aureus, Salmonella typhimurium, Pseudomonas aeruginosa and Bacillus subtilis. Only one of these compounds shows promising results against S. aureus and S. typhi. Cytotoxicity screening on human leukemic promyelocyte HL-60 cells found that two of these compounds were very active with CD₅₀ values of 0.87 and 0.18 µg mL⁻¹. Conclusion: The studied compounds were found to have the potential in biological activity especially in cytotoxicity where this possibly can be used for clinical trials after further research.