Synthesis and antibacterial study of unsaturated Mannich ketones

• Published in: European journal of medicinal chemistry 2001-09, Vol.36 (9), p.705-717
• Main Authors: Lóránd, Tamás, Kocsis, Béla, Sohár, Pál, Nagy, Gergely, Kispál, Gyula, Krane, Hans-Georg, Schmitt, Horst, Weckert, Edgar
• Format: Article
• Language: English
• Subjects: antibacterial activity; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Bacillus subtilis - drug effects; Biological and medical sciences; Crystallography, X-Ray; cytotoxicity; Escherichia coli - drug effects; HeLa Cells; Humans; Magnetic Resonance Spectroscopy; Mannich Bases - chemical synthesis; Mannich Bases - pharmacology; Mannich ketone; Medical sciences; Microbial Sensitivity Tests; Micrococcus luteus - drug effects; NMR; Pharmacology. Drug treatments; Pseudomonas aeruginosa - drug effects; Spectrophotometry, Infrared; Staphylococcus aureus - drug effects; Stereoisomerism; Structure-Activity Relationship
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/S0223-5234(01)01264-8

Several Mannich ketones of 2-arylmethylenecycloalkanones were synthesised using the classical acid-catalysed Mannich reaction. Antibacterial activity of these new water-soluble compounds was reported against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Staphylococcus saprophyticus, Micrococcus luteus and Bacillus subtilis standard strains. Human cell line cytotoxicity of our new compounds was evaluated against HeLa cell lines. Some compounds showed low cytotoxicity (41.52 nM mL −1 for 14 and 46.60 nM mL −1 for 18) and proved to be efficient antibacterial agents against the Gram-positive strains. Minimum inhibitory concentrations varied from 1.56 to 100 μg mL −1. The mechanism of action was examined, too.