Design, Synthesis, and Biological Evaluation of New Azulene-Containing Chalcones

Azulene-containing chalcones have been synthesized via Claisen-Schmidt condensation reaction. Their chemical structure has been established by spectroscopic methods where the H-NMR spectra suggested that the title chalcones were geometrically pure and configured (J = 15 Hz). The influence of functio...

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Bibliographic Details
Published in:Materials 2022-02, Vol.15 (5), p.1629
Main Authors: Bala, Daniela, Jinga, Luiza-Izabela, Popa, Marcela, Hanganu, Anamaria, Voicescu, Mariana, Bleotu, Coralia, Tarko, Laszlo, Nica, Simona
Format: Article
Language:English
Subjects:
Antiinfectives and antibacterials
Azulene
Bacteria
Biological activity
Chromatography
Fluorescence
Functional groups
Fungicides
Microorganisms
NMR
Nuclear magnetic resonance
Substitution reactions
Toxicity
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Summary:Azulene-containing chalcones have been synthesized via Claisen-Schmidt condensation reaction. Their chemical structure has been established by spectroscopic methods where the H-NMR spectra suggested that the title chalcones were geometrically pure and configured (J = 15 Hz). The influence of functional groups from azulene-containing chalcones on the biological activity of the 2-propen-1-one unit was investigated for the first time. This study presents optical and fluorescent investigations, QSAR studies, and biological activity of 10 novel compounds. These chalcones were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria. The results revealed that most of the synthesized compounds showed inhibition against Gram-negative microorganisms, independent of the substitution of azulene scaffold. Instead, all azulene-containing chalcones exhibited good antifungal activity against , with MIC values ranging between 0.156 and 0.312 mg/mL. The most active compound was chalcone containing azulene moieties on both sides of the 2-propene-1-one bond, exhibiting good activity against both bacteria-type strains and good antifungal activity. This antifungal activity combined with low toxicity makes azulene-containing chalcones a new class of bioorganic compounds.
ISSN:1996-1944
1996-1944
DOI:10.3390/ma15051629