A series of diiron complexes with two cyclopentadienyls, two carbonyls, and one bridging vinyl-aminoalkylidene as ligands, [3a–h]CF3SO3 and [4a–d]CF3SO3, was synthesized in 66–94% yields from diiron μ-aminocarbyne precursors. The subsequent reactions with pyrrolidine led to selective fragmentation to aminoalkylidene-ferracyclopentenone derivatives (5a–h and 6a–c) in 30–84% yields. The compounds were characterized by elemental analysis, Fourier transform infrared and NMR spectroscopy, and by single crystal X-ray diffraction in three cases. The stability in aqueous media relevant to biological trials, the carbon monoxide release, and the catalytic activity in NADH oxidation were evaluated for selected compounds by NMR spectroscopy and gas chromatography. The in vitro antiproliferative activity of the compounds was determined towards cancer (A2780, A2780cisR) and noncancer (HEK-293) cell lines. Moreover, the antibacterial activity was tested on Gram-positive (vancomycin-resistant E. faecium and methicillin-resistant S. aureus) and Gram-negative strains (A. baumannii and P. aeruginosa).
Antiproliferative and bactericidal activity of diiron and monoiron cyclopentadienyl carbonyl complexes comprising a vinyl-aminoalkylidene unit
Biancalana L.;Zacchini S.;Pampaloni G.;F. Marchetti
2020-01-01
Abstract
A series of diiron complexes with two cyclopentadienyls, two carbonyls, and one bridging vinyl-aminoalkylidene as ligands, [3a–h]CF3SO3 and [4a–d]CF3SO3, was synthesized in 66–94% yields from diiron μ-aminocarbyne precursors. The subsequent reactions with pyrrolidine led to selective fragmentation to aminoalkylidene-ferracyclopentenone derivatives (5a–h and 6a–c) in 30–84% yields. The compounds were characterized by elemental analysis, Fourier transform infrared and NMR spectroscopy, and by single crystal X-ray diffraction in three cases. The stability in aqueous media relevant to biological trials, the carbon monoxide release, and the catalytic activity in NADH oxidation were evaluated for selected compounds by NMR spectroscopy and gas chromatography. The in vitro antiproliferative activity of the compounds was determined towards cancer (A2780, A2780cisR) and noncancer (HEK-293) cell lines. Moreover, the antibacterial activity was tested on Gram-positive (vancomycin-resistant E. faecium and methicillin-resistant S. aureus) and Gram-negative strains (A. baumannii and P. aeruginosa).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
