Antibacterial 3-(arylamino)-1-ferrocenylpropan-1-ones: Synthesis, spectral, electrochemical and structural characterization

• Published in: Journal of organometallic chemistry Vol. 696; no. 23; pp. 3703 - 3713
• Main Authors: Damljanovic, Ivan, Stevanovic, Dragana, Pejovic, Anka, Vukicevic, Mirjana, Novakovic, Sladjana B., Bogdanovic, Goran A., Mihajlov-Krstev, Tatjana, Radulovic, Niko, Vukicevic, Rastko D.
• Format: Journal Article
• Language: English
• Published: LAUSANNE Elsevier B.V 15.11.2011; Elsevier
• Subjects: 3-(Arylamino)-1-ferrocenylpropan-1-ones; Acryloylferrocene; Antibacterial activity; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; Mannich bases; Microwave irradiation; Montmorillonite K-10; Physical Sciences; Science & Technology; Montmorillonite K-10; Microwave irradiation; Antibacterial activity; Acryloylferrocene; 3-(Arylamino)-1-ferrocenylpropan-1-ones; Mannich bases; FRIEDEL-CRAFTS ACYLATION; AZA-MICHAEL ADDITION; ALPHA,BETA-UNSATURATED COMPOUNDS; EFFICIENT SYNTHESIS; ANTITUMOR-ACTIVITY; AROMATIC-AMINES; SOLVENT-FREE; ALIPHATIC-AMINES; CONJUGATE ADDITION; MANNICH-BASES
• DOI: 10.1016/j.jorganchem.2011.08.016
• ISSN: 0022-328X

Syntheses of fourteen new 3-(arylamino)-1-ferrocenylpropan-1-ones have been achieved in good to excellent yields by an aza-Michael addition of different arylamines to acryloylferrocene. The reaction was performed by microwave (MW) irradiation (500 W/5 min) of a mixture of reactants and montmorillonite K-10, without a solvent. The obtained compounds were spectrally and electrochemically (cyclic voltammetry) fully characterized, whereas single-crystal X-ray analysis has been performed for three of them. In a microdilution assay, all of the compounds were shown to have a broad-spectrum effect on Gram-negative and -positive bacteria, although the degree of inhibition varied. A notable activity was observed for all compounds in inhibiting the growth of an important human pathogen Staphylococcus aureus. An aza-Michael addition of arylamines to acryloylferrocene in good to excellent yields that proceeds in 5 min under microwave irradiation and solvent-free conditions and employs a cheap and environmentally friendly catalyst (montmorillonite K-10) is described. Fourteen newly synthesized compounds were full spectrally and electrochemically characterized. The structures of three compounds were corroborated by X-ray single-crystal analysis. The synthesized compounds showed broad-spectrum effect on Gram (−) and (+) bacteria and were especially active against Staphylococcus aureus. [Display omitted] ► Michael addition of arylamines to acryloylferrocene in good to excellent yields. ► Proceeds in 5 min under microwave irradiation and solvent-free conditions. ► Employs a cheap and environmentally friendly catalyst (montmorillonite K-10). ► Full spectral and electrochemical characterization of 14 new synthesized compounds. ► Broad-spectrum effect on Gram (−) and (+) bacteria and especially against S. aureus.