Biologically Active New N, N', N''-Tri-Substituted Ferrocenyl Phenylguanidines and their Characterization

Abstract

The results revealed that the ferrocene incorporation to guanidines enhances their DNA binding ability. A similar trend was found in antioxidant and antimicrobial studies. Being the bioactive molecules these compounds are potential drug candidates.

Synthesis and Biological Evaluation of Some New Ferrocenyl Phenyl Guanidines as Antibacterial, Antifungal Agents

“…The syntheses of the ferrocenylphenylguanidines (d-1 to d-4) were achieved in four steps [19]. In the first step; nitrophenylferrocene (a) was made by the coupling of ferrocene with diazonium salts of corresponding nitroaniline using phase transfer catalyst (CTAB.…”

“…Incorporation of phenyl groups on guanidine moiety may decrease the bascicity of guanidines and increase theirlipophylicity and in turn increase the antibacterial and antifungal activies as reported [18]. Introduction of electronegative groups and ferrocene atthe phenyl groupsof N, N´, N´´-triphenylguanidinesprovide extended conjugation and further increase in lipophylicity as Antibacterial, Antifungal Agents and an increase in the antimicrobial activities was observed and reported [19]. In the present work the extended delocalization due to ferrocene was decreased by its incorruption at the meta position of phenyl ring and the effect on antimicrobial activities was determined.…”

“…13 C and 1 H-NMR spectra were recorded on a Bruker-300 MHz spectrometer in CDCl 3 using tetra methyl silane (TMS) as an internal reference. (1.95g, 6mmol) were mixed with the 3ferrocenyl aniline (1.66g, 6mmol) in 20ml dimethylformamide (DMF) with two equivalents of triethylamine (1.7ml, 12mmol) [19]. Keeping the temperature below 5ºC, Mercuric chloride (1.63g, 6mmol) was added with strong stirring of the reaction mixture.…”