Please use this identifier to cite or link to this item: https://scidar.kg.ac.rs/handle/123456789/10505
Title: Sulfur-containing ferrocenyl alcohols and oximes: New promising antistaphylococcal agents
Authors: Ilic, Dragana
Damljanović, Ivan
Stevanović, Dragana
Vukićević, Miomir
Blagojevic, Polina
Radulovic, Niko
Vukicevic R.
Issue Date: 2012
Abstract: 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 ï¿CH(OH)(CH2)nSï¿ and ï¿CH(ïNOH)(CH2)nSï¿ (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. © 2012 Verlag Helvetica Chimica Acta AG, Zürich.
URI: https://scidar.kg.ac.rs/handle/123456789/10505
Type: article
DOI: 10.1002/cbdv.201200029
ISSN: 1612-1872
SCOPUS: 2-s2.0-84867757098
Appears in Collections:Faculty of Science, Kragujevac

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