Perspectives of ferrocenyl chalcones: synthetic scaffolds toward biomedical and materials science applications

Abstract

Ferrocene and its derivatives constitute versatile and interesting scaffolds for the global chemical enterprise due to its multiple applications that range from biomedical to materials science. Ferrocenyl derivatives are the leading compounds in our research for the syntheses and characterization as well as their potential biological applications. Among them, our recent focus has been in ferrocenyl chalcones as a framework for further derivatization. The proposed modifications consist on the incorporation of heterocyclic moieties into the ferrocenyl chalcone core. This can be afforded either by introducing a heterocyclic aromatic moiety as a substituent or functionalizing the α-β unsaturated system. Another modification explored is the formation of ammonium or pyridinium salts to increase water solubility. Studied ferrocenyl chalcones exhibit remarkable stability, physical, and electrochemical properties. These factors have led the approaches for them to be precursors of biologically active compounds (cancer, bacteria, malaria, and neurobiological diseases). Moreover, other potential applications include molecular materials, redox-sensors, and polymers. Our goal in this mini review is to highlight the chemistry of ferrocene derivatives with particular prominence to those ferrocenyl chalcones studied in our laboratory and their applications. Moreover, we are providing a background on ferrocene, chalcones, and ferrocenyl chalcones, emphasizing the methodologies with preeminent yields.

In vitro antioxidant activity evaluation of ferrocenyl chalcones

“…The FT-IR/ATR spectra of all synthesized compounds were recorded in the wavelength range 400-4000 cm -1 using a Thermo ScientificNicolet iS10 apparatus. 1 H and 13 C NMR spectra of compounds 1 ̶ 3 were recorded on a Bruker Ascend 400 apparatus at room temperature in deuterated chloroform (CDCl3), while spectra of compounds 4 and 5 were recorded in deuterated dimethyl sulfoxide (DMSO-d6). All melting points were determined on Electrothermal apparatus.…”

“…Singh et al demonstrated that ferrocene appended chalcone linked triazole allied organosilatranes possess high radical scavenging efficacy [9]. Moreover, other potential applications of investigated derivatives include molecular materials, redox-sensors, and polymers [1]. Our goal in this paper is to highlight the synthesis and antioxidant activity of ferrocenyl chalcones (Scheme 1) with particular prominence to the most active derivatives which represent an interesting starting point for the synthesis of some new pharmacologically active compounds.…”

“…Ferrocene and its derivatives represent the leading compounds for the global chemical enterprise due to its multiple applications that range from biomedical to materials science [1]. In addition, chalcones represent naturally occurring derivatives of the parent compound 1,3-diphenyl-2propen-1-one, pertaining to the flavonoid family of organic compounds.…”

Inhibition of Cathepsin B by Ferrocenyl Indenes Highlights a new Pharmacological Facet of Ferrocifens

“…A novel strategy based on multifunctional hybrids of ferrocene was then considered. This approach has recently been the subject of a large number of reviews [5][6][7][8][9][10][11][12][13][14][15][16] and the results have proved to be, to say the least, mixed. Nonetheless the redox motif [ferrocenyl-ene-phenol] remains the most biologically promising candidate to date, since compounds presenting this motif show remarkable antitumor properties both in vitro and in vivo.…”

Enantioselective Synthesis of Planar Chiral Ferrocifens that Show Chiral Discrimination in Antiproliferative Activity on Breast Cancer Cells

“…In the realm of bio‐organometallic chemistry, the ferrocifen system continues to attract significant attention . These molecules possess a ferrocenyl‐ene‐ p ‐phenol motif, and a basic dimethylaminoalkoxy chain, as in 3 .…”