Synthesis, characterization and antimicrobial activity of novel ferrocene containing quinolines: 2-ferrocenyl-4-methoxyquinolines, 1-benzyl-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-ones and 1-benzyl-2-ferrocenylquinolin-4(1H)-ones

• Published in: Journal of organometallic chemistry Vol. 846; pp. 6 - 17
• Main Authors: Pejovic, Anka, Damljanovic, Ivan, Stevanovic, Dragana, Minic, Aleksandra, Jovanovic, Jovana, Mihailovic, Vladimir, Katanic, Jelena, Bogdanovic, Goran A.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 01.10.2017; Elsevier
• Subjects: 2,3-Dihydroquinolin-4(1H)-ones; Antimicrobial activity; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Electrochemistry; Ferrocene; Physical Sciences; Quinolin-4(1H)-ones; Quinolines; Science & Technology; Quinolines; Electrochemistry; Antimicrobial activity; 2,3-Dihydroquinolin-4(1H)-ones; Quinolin-4(1H)-ones; Ferrocene; IN-VITRO; QUINOLONES; STRUCTURAL-CHARACTERIZATION; ANTIMALARIAL ACTIVITY; DERIVATIVES
• ISSN: 0022-328X; 1872-8561
• DOI: 10.1016/j.jorganchem.2017.05.051

A three new series of the ferrocene containing quinolines – 2-ferrocenyl-4-methoxyquinolines, 1-benzyl-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-ones and 1-benzyl-2-ferrocenylquinolin-4(1H)-ones – were synthesized in order to test their in vitro antimicrobial activity against six strains of bacteria and one fungal/yeast strain. It has been shown that all 21 quinolines are completely inactive against the Gram-positive bacteria at tested dose, while their activities on the other strains were noteworthy. All new compounds were characterized by the IR and NMR spectral data, and their electrochemical properties were investigated by the cyclic voltammetry. The X-ray crystal structure of one of the representative quinolin-4(1H)-ones is also presented. [Display omitted] •Synthesis of novel bioactive ferrocene containing quinoline derivatives.•Effective oxidations to quinolone derivatives by two easily accessible reagents.•Full spectral and electrochemical characterization of 21 new synthesized compounds.•All tested ferrocene compounds displayed broad-spectrum effect on Gram (−) bacteria.•All tested ferrocene compounds displayed the best activity against yeast C. albicans.