The Synthesis, Structure And Properties Of Ferrocenyl-oxadiazoles Derivatives

Ferrocene and its derivatives play an important role in catalysis, materials,molecular recognition and electrochemistry with its unique sandwich structure.1,3,4-oxadiazoles attract an increasingly attention due to their special and extensivephysiological activity, optical activity and the application in medicine andpesticide. Therefore, in the case of adding the1,3,4-oxadiazoles unit to thestructure of ferrocene, we get a series of compounds which have broad-spectrumelectrochemical and biological activities. In this paper, we use ferrocene and2,5-disubstituted1,3,4-oxadiazoles as raw materials to synthesize ten ferrocenyl-oxadiazole derivatives. We also studied their quantum chemistry calculation andtheir electrochemical and biological activities.1. Five new Ferrocene-2-carboxylic acid (5-phenyl-[1,3,4]oxadiazol-2-yl)-amidecompounds were obtained by condensation, oxidization and acylationreactions, using ferrocenecarboxylic acid, benzaldehyde,4-methyl benzaldehyde,4-methoxybezaldehyde,4-chlorobenzaldehyde and4-bromobenzaldehyde assubstrates, respectively. These compounds were characterized by IR,1H NMR,MS and elemental analysis. Their UV-vis spectral, fluorescence, the response tometal ions, electrochemistry and biological activity were studied.2. Five2-4-Ferrocene-2-yl-4-oxo-N-(5-phenyl-[1,3,4]oxadiazol-2-yl)-butyramidecompounds were obtained by condensation, oxidization and acylation reactions,using3-ferrocenoylpropionic acid, benzaldehyde,4-methyl benzaldehyde,4-methoxybezaldehyde,4-chlorobenzaldehyde and4-bromobenzaldehyde assubstrates, respectively with HBTU as contracting reagent. These compoundswere characterized by IR,1H NMR, MS and elemental analysis. Their UV-visspectral, fluorescence, electrochemistry, the response to metal ions, andbiological activity were studied.3. Electrochemical study showed that single electronic redox reaction happened onthe surface of electrode which indicated that the electrochemical environment offerrocenyl were fundamentally the same and the reaction on the electrode werecontrolled by diffusion of these ten new ferrocene derivatives.4. Those compounds all showed good antibacterial properties to Colibacillus, andpoor antibacterial properties to Staphylococcus aureus. The first group displayed relatively good inhibitive ability to HepG-2, MGC-803and weak inhibitiveability to McF-7. The second group displayed relatively weak inhibitive ability toHepG-2, MGC-803and McF-7.