70574-30-0

Upstream product

• 32846-80-3 S-isopropyl methanethiosulfonate 
• 4875-10-9 o-nitrothiophenol 
• 75-30-9 2-iodo-propane 
• 118209-13-5 2-nitrophenyl disulphide anion 

Relevant academic research and scientific papers

Unsymmetric aryl-alkyl disulfide growth inhibitors of methicillin-resistant Staphylococcus aureus and Bacillus anthracis

This study describes the antibacterial properties of synthetically produced mixed aryl-alkyl disulfide compounds as a means to control the growth of Staphylococcus aureus and Bacillus anthracis. Some of these compounds exerted strong in vitro bioactivity. Our results indicate that among the 12 different aryl substituents examined, nitrophenyl derivatives provide the strongest antibiotic activities. This may be the result of electronic activation of the arylthio moiety as a leaving group for nucleophilic attack on the disulfide bond. Small alkyl residues on the other sulfur provide the best activity as well, which for different bacteria appears to be somewhat dependent on the nature of the alkyl moiety. The mechanism of action of these lipophilic disulfides is likely similar to that of previously reported N-thiolated β-lactams, which have been shown to produce alkyl-CoA disulfides through a thiol-disulfide exchange within the cytoplasm, ultimately inhibiting type II fatty acid synthesis. However, the mixed alkyl-CoA disulfides themselves show no antibacterial activity, presumably due to the inability of the highly polar compounds to cross the bacterial cell membrane. These structurally simple disulfides have been found to inhibit β-ketoacyl-acyl carrier protein synthase III, or FabH, a key enzyme in type II fatty acid biosynthesis, and thus may serve as new leads to the development of effective antibacterials for MRSA and anthrax infections.

N-alkylthio beta-lactams, alkyl-coenzyme a asymmetric disulfides, and aryl-alkyl disulfides as anti-bacterial agents

The present invention provides N-alkylthio β-lactams and disulfide compounds (e.g., alkyl-coenzyme A asymmetric disulfides or aryl-alkyl disulfides), compositions containing such compounds, and method of their use as anti-bacterial agents.

Relative Nucleophilicities of Aryldisulphide and Thiolate Ions in Dimethylacetamide Estimated from their Reaction Rates with Alkyl Halides

The relative rates of nucleophilic substitution (SN2) of alkyl halides by aromatic thiolates ArS- and aryldisulphide ions ArS2- have been studied in dimethylacetamide by UV-visible spectrophotometry for Ar = 4-nitrophenyl (1), 2-nitrophenyl (2), and 8-quinolyl (3).Rate constants are relative to the rate constants for benzenethiolate ions (4), studied as reference.With Ar = (1), the reaction rate for disulphide ions is ten times higher than that for monosulphide ions stabilized by the elevated delocalization of their charge.With Ar = (2) and (3), the reactivity of disulphide ions is higher than that of the corresponding thiolates.Our study is consistent with the uncomplicated introduction of a disulphide bond into various substrates from aryldisulphide ions stabilized in aprotic dipolar media.