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Synthesis and Spectral Characterization of Asymmetric Azines Containing a Coumarin Moiety: The Discovery of New Antimicrobial and Antioxidant Agents
Author(s) -
Ristić Milenko N.,
Radulović Niko S.,
Dekić Biljana R.,
Dekić Vidoslav S.,
Ristić Novica R.,
StojanovićRadić Zorica
Publication year - 2019
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201800486
Subject(s) - chemistry , antimicrobial , moiety , dpph , coumarin , antioxidant , hydrazone , stereochemistry , carbon 13 nmr , organic chemistry , combinatorial chemistry
Nine unsymmetrical azines containing a coumarin moiety were prepared by the reaction of the hydrazone of 4‐hydroxy‐3‐acetylcoumarin with differently substituted aromatic aldehydes. The azines were fully spectrally characterized, including a complete assignment of 1 H‐ and 13 C‐NMR resonances, and were assessed for their acute toxicities in the Artemia salina model. Their free radical scavenging activities were tested in the DPPH assay, and in vitro antimicrobial activities were determined against seven bacterial and two fungal strains. The azines containing a p ‐hydroxyphenyl group were shown to be the most effective antimicrobial agents, and in the case of resistant strains of Staphylococcus aureus and Acinetobacter baumannii , the activity was comparable to that of chloramphenicol. The derivative having a 3,5‐dimethoxy‐4‐hydroxyphenyl group exhibited pronounced antioxidant power reacting rapidly and in 1 : 1 mol ratio with the DPPH radical.