360774-36-3

Upstream product

• 102-54-5 ferrocene 
• 23909-00-4 3-(2,6-dichlorobenzylthio)-propanoic acid 

Downstream Products

• 1415679-00-3 3-[(2,6-dichlorophenyl)methylsulfanyl]-1-ferrocenylpropan-1-ol 

Relevant academic research and scientific papers

Sulfur-containing ferrocenyl alcohols and oximes: New promising antistaphylococcal agents

A small library containing four different series of new ferrocene derivatives, 2-(alkylsulfanyl)-1-ferrocenylethan-1-ols, 3-(alkylsulfanyl)-1- ferrocenylpropan-1-ols, (E)- and (Z)-2-(alkylsulfanyl)-1-ferrocenylethan-1-one oximes, and (E)- and (Z)-3-(alkylsulfanyl)-1-ferrocenylpropan-1-one oximes (36 different compounds in total) was synthesized starting from ferrocene and the corresponding sulfanyl acids. All compounds were spectrally (IR and NMR) and electrochemically characterized. In general, the obtained compounds were found to exhibit very strong antimicrobial activities (broth microdilution assay) against the tested microorganisms (six common human pathogens). For the majority of the tested compounds, the determined MIC values were either under the 10μg/ml MIC limit recognized to delimit efficient antimicrobials or were comparable to/lower than those of the used positive controls (tetracycline/nystatin). The most susceptible organism was found to be Staphylococcus aureus with MIC values even reaching 0.001μg/ml. The presence of iCH(OH)(CH2)nSi and iCH(iNOH)(CH2)nSi (n=1 or 2) structural fragments seems to be essential for the observed strong activity (introduction of hydroxyimino and alcohol functionalities, instead of the keto function, resulted in a more than 105-fold increase in antistaphylococcal activity in some instances). Nevertheless, a possible influence of the ferrocenyl-core redox chemistry (Fe2+/Fe 3+) should not be disregarded. The studied alcohols exhibited a reversible one-electron redox couple at almost the same position as ferrocene, while the hydroxyimino group conjugated with cyclopentadienyl ring considerably shifted the redox potential of the ferrocene unit in oximes.

Synthesis, spectral characterization, electrochemical properties and antimicrobial screening of sulfur containing acylferrocenes

Several known and eight new sulfur containing acylferrocenes of the general formula FcCO(CH2)nSR (where Fc = ferrocenyl, n = 1 or 2 and R = alkyl, 4-bromobenzyl or 2,6-dichlorobenzyl group) were synthesized in order to test their in vitro antimicrobial activity against 11 bacterial and three fungal/yeast strains. It has been shown that only four of the 14 ketones are completely inactive at the tested dose, while the activities of the other ones were noteworthy. All new compounds were well characterized by IR and NMR spectral data, and their electrochemical properties were investigated by cyclic voltammetry. The X-ray crystal structures of two representative ketones are also presented.