Syntheses and Characterization of Ferrocenyl Chalcones
Otaño Vega, Myrna R.
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Bioorganometallic chemistry was revolutionized with the inclusion of the ferrocene moiety in well-known organic molecules. Ferrocene derivatives have gained importance due to their excellent stability in aqueous, aerobic media, the easy accessibility to a large variety of derivatives, and ideal electrochemical properties. Tamoxifen is one example in which one aromatic ring was replaced with a ferrocene leading to a more active species, ferrocifen. Ferrocenyl chalcones are a family of 1,3-diphenyl-2-propen-1-one in which one phenyl group is replaced with the ferrocene moiety. In this research the synthesis and characterization of five families of ferrocenyl chalcones is discussed: mono-, symmetric-substituted, cyclic, and nonsymmetric ferrocenyl chalcones in addition to the synthesis, characterization and preliminary anti-bacterial activity of Curcumin analogues. A total of eleven new derivatives were synthesized. Each compound was characterized by NMR spectroscopy, FT-IR, melting point determination, elemental analyses, CV, and UV-Vis spectroscopy. In addition, four new X-ray crystal structures are presented. The mono- and symmetric-substituted ferrocenyl chalcones have been synthesized via the classical base-catalyzed Claisen–Schmidt condensation reaction in ethanol solvent and solvent-free media. The first family of ferrocenyl chalcones was the mono-substituted derivatives and is discussed in Chapter 2. A total of twenty two of these chalcones, four of them new derivatives, were synthesized with yields ranging between 40–94% after recrystallization. Also, two new X-ray crystal structures were elucidated. The second family, the symmetric-substituted chalcones, is discussed in Chapter 3. For this family, four new derivatives were synthesized and characterized with 37-82% yields and four other derivatives were attempted. Moreover, two new X-ray crystal structures of these derivatives were also elucidated. A third family, the ferrocenophane,which is a cyclic derivative, were also synthesized and characterized. The fourth family is the non-symmetric ferrocenyl chalcones. One new derivative was synthesized in 60% yield via the Fridel-Crafts acylation of a ferrocenyl chalcone. In addition, attempts to synthesize two other nonsymmetrical ferrocenyl derivatives are discussed in Chapter 4. Finally, the synthesis and characterization of curcumin analogues is presented. A new ferrocenyl chalcone, 1-ferrocenyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one, which we commonly name as Monocurcumin, was synthesized in 27% yield after column chromatography by a pyrrolidine-catalyzed reaction. Preliminary studies on its susceptibility against B. cereus, S. sapro, S. aureus, K. pneumonia, E. coli and, P. aeruginosa bacteria are presented. This derivative showed a MIC of 1.95 μM against Gram-positive B. cereus, S. sapro, S. aureus and Gram-negative K. pneumonia bacteria.