Synthesis, characterization and biological activities of organotin (IV) methylcyclohexyldithiocarbamate compounds

Normah Awang, Ibrahim Baba, Bohari Mohd. Yamin, Mohd. Sham Othman, Kamaludin Nurul Farahana

Research output: Contribution to journalArticle

18 Citations (Scopus)

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 RmSn[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.

Original languageEnglish
Pages (from-to)310-317
Number of pages8
JournalAmerican Journal of Applied Sciences
Volume8
Issue number4
Publication statusPublished - 2011

Fingerprint

Cytotoxicity
Bioactivity
Organotin Compounds
Salmonella
Chemical shift
Bacilli
Chelation
Chemical analysis
Sulfur
Nuclear magnetic resonance spectroscopy
Industrial applications
Bacteria
Screening
Carbon
Nuclear magnetic resonance
Single crystals
Ligands
Infrared radiation
Atoms

Keywords

  • Antibacterial activity
  • Biological activities
  • Disc diffusion
  • Elemental analysis
  • Infrared spectra
  • Salmonella typhimurium
  • Staphylococcus aureus
  • Synthesized compounds

ASJC Scopus subject areas

  • General

Cite this

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title = "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 RmSn[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.",
keywords = "Antibacterial activity, Biological activities, Disc diffusion, Elemental analysis, Infrared spectra, Salmonella typhimurium, Staphylococcus aureus, Synthesized compounds",
author = "Normah Awang and Ibrahim Baba and {Mohd. Yamin}, Bohari and Othman, {Mohd. Sham} and {Nurul Farahana}, Kamaludin",
year = "2011",
language = "English",
volume = "8",
pages = "310--317",
journal = "American Journal of Applied Sciences",
issn = "1546-9239",
publisher = "Science Publications",
number = "4",

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TY - JOUR

T1 - Synthesis, characterization and biological activities of organotin (IV) methylcyclohexyldithiocarbamate compounds

AU - Awang, Normah

AU - Baba, Ibrahim

AU - Mohd. Yamin, Bohari

AU - Othman, Mohd. Sham

AU - Nurul Farahana, Kamaludin

PY - 2011

Y1 - 2011

N2 - 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 RmSn[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.

AB - 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 RmSn[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.

KW - Antibacterial activity

KW - Biological activities

KW - Disc diffusion

KW - Elemental analysis

KW - Infrared spectra

KW - Salmonella typhimurium

KW - Staphylococcus aureus

KW - Synthesized compounds

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