Novel enaminones as non-cytotoxic compounds with mild antibacterial activity: Synthesis and structure-activity correlations (CROSBI ID 245370)
Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija
Podaci o odgovornosti
Cindrić, Marina ; Rubčić, Mirta ; Hrenar, Tomica ; Pisk, Jana ; Cvijanović, Danijela ; Lovrić, Jasna ; Vrdoljak, Višnja
engleski
Novel enaminones as non-cytotoxic compounds with mild antibacterial activity: Synthesis and structure-activity correlations
Six non−symmetric enaminones 4-[(2-hydroxy-5- methylphenyl)amino]pent-3-en-2-one (H2L1), 4- [(2- hydroxy-4- methylphenyl)amino]pent-3-en-2- one (H2L2), 4-[(4-hydroxy-2- methylphenyl)amino)]pent- 3-en-2-one (H2L3), 3- [(2-hydroxy- 5- methylphenyl)amino]-1-phenylbut- 2-en-1-one (H2L4), 3-[(2- hydroxy-4- methylphenyl)amino]-1- phenylbut-2-en-1-one (H2L5) and 3-[(4-hydroxy-2- methylphenyl)amino]-1-phenylbut- 2-en-1-one (H2L6) have been prepared by solution based method. The enaminones were characterized by elemental and DSC analysis, NMR and IR spectroscopy. Crystal and molecular structures of H2L1, H2L2, H2L4 and H2L6 were determined via single crystal X−ray analysis. The prepared enaminones were screened against THP- 1 and HepG2 cells, and Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Moraxella catarrhalis bacteria to assess their cytotoxic and antibacterial activity, respectively. All compounds proved to be non- cytotoxic and showed mild or no antibacterial activity. Quantum mechanical calculations suggest that the presence of hydroxy group in ortho position, combined with the methyl group on the same aromatic ring, has a significant impact on the biological activities.
crystal and molecular structure ; acyclic enaminones ; theoretical calculations
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Podaci o izdanju
1154
2018.
636-642
objavljeno
0022-2860
1872-8014
10.1016/j.molstruc.2017.10.078