Synthesis, physicochemical properties and antimicrobial activity of mono-/dinitroxyl amides.
Two comparative sets of mono-/dinitroxyl amides were designed and prepared. The novel TEMPO and/or PROXYL derivatives were fully characterised and their spin, redox and antimicrobial properties were determined. Cyclic voltammetry revealed (quasi)reversible redox behavior for most of the studied radicals. Moreover, the electron-withdrawing substituents increased the oxidation potential of nitroxides in comparison to electron-donating groups. While EPR spectra of monoradicals featured the typical three-line signal, the spectra of biradicals showed more complex splitting patterns. The in vitro biological assay revealed that unlike pyrrolidinyl derivatives, the piperidinyl nitroxides significantly inhibited the growth of Staphylococcus sp.
Department of Organic Chemistry, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia. peter.szolcsanyi@stuba.sk.
Miroslav
M
Kavala
Vlasta
V
Brezová
Lubomír
L
Švorc
Zuzana
Z
Vihonská
Petra
P
Olejníková
Ján
J
Moncol
Jozef
J
Kožíšek
Peter
P
Herich
Peter
P
Szolcsányi
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D055598:Chemical Phenomena; D003198:Computer Simulation; D003497:Cyclic N-Oxides / Q000138:chemical synthesis / Q000737:chemistry; D055664:Electrochemical Techniques; D004566:Electrodes; D004578:Electron Spin Resonance Spectroscopy; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009589:Nitrogen Oxides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010084:Oxidation-Reduction; D013210:Staphylococcus / Q000187:drug effects; D014961:X-Ray Diffraction
D000577:Amides; D000890:Anti-Infective Agents; D003497:Cyclic N-Oxides; D009589:Nitrogen Oxides; C003959:TEMPO