Abstract
Azulene-containing chalcones have been synthesized via Claisen–Schmidt condensation reaction. Their chemical structure has been established by spectroscopic methods where the 1H-NMR spectra suggested that the title chalcones were geometrically pure and configured trans (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 Candida parapsilosis, 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.
Highlights
The spread of antibiotic-resistant pathogenic microorganisms represents a serious concern of the scientific community; the development of newer drugs with increased effect against broad strains of bacteria is imperative
Tehree apbsroerppatiroend accor rsflpeupeocroterrsatcewednecrepeerrmoecciosesrdidouendrseopsnec[at1rVa3a]wr.ieTarnehCreeacIroRyrd1se0pd0eascpttrerocaotrm(oKptheBmortpopemeraelltteuertrse()PwawiltoheAraelJtaocs,ocCollAFeP,cU-t6eS5dA00)o.snTpehace-Bruker 3tr7oflsupoercotmroetmere(Mtearr(yE’stCtloinugrteEna,stGone,rMmDa,nUyS)Ai)netqhueip4p0ed0–w4i0th00a 1c5m0 W−1 rxaenngone.laTmhpeuNsinMgR spect recorded on a Bruker Ultrashield Advance III 500 MHz spectrometer (Karlsruh many); the chemical shifts expressed as δ values are reported relative to sidual proton NMR resonances of the deuterated solvent
The antimicrobial activity of all compounds was assessed on Gram-positive bacteria (Staphylococcus aureus ATCC 25923), Gram-negative bacteria (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853), and fungi (Candida parapsilosis ATCC 22019) using quantitative binary serial dilution method in 96-well plates [28,29]
Summary
The spread of antibiotic-resistant pathogenic microorganisms represents a serious concern of the scientific community; the development of newer drugs with increased effect against broad strains of bacteria is imperative. Special attention has been paid to chalcones, a class of organic compounds with a broad range of biological activities, including antibacterial, antitumor, antimalarial, anti-inflammatory, and anti-HIV activities [1,2,3,4]. The chemical structure consisting of two aromatic rings joined by an α,β-unsaturated carbonyl system (Scheme 1), which is available via easy organic synthesis, has generated intensive. In this context, we describe her cGheenmeraicl aElxpseyrnimtheenstaisl ,Inofportmicaatlioannd fluorescence investigations, QSAR studies, and bi activUitnyleossf o1t0henrowviseel satzautelde,nteh‐ecoconmtaminericniagllcyhaavlaciolanbeles.chemicals and solvents were used as received. Tehree apbsroerppatiroend accor rsflpeupeocroterrsatcewednecrepeerrmoecciosesrdidouendrseopsnec[at1rVa3a]wr.ieTarnehCreeacIroRyrd1se0pd0eascpttrerocaotrm(oKptheBmortpopemeraelltteuertrse()PwawiltoheAraelJtaocs,ocCollAFeP,cU-t6eS5dA00)o.snTpehace-Bruker 3tr7oflsupoercotmroetmere(Mtearr(yE’stCtloinugrteEna,stGone,rMmDa,nUyS)Ai)netqhueip4p0ed0–w4i0th00a 1c5m0 W−1 rxaenngone.laTmhpeuNsinMgR spect recorded on a Bruker Ultrashield Advance III 500 MHz spectrometer (Karlsruh many); the chemical shifts expressed as δ (ppm) values are reported relative to sidual proton NMR resonances of the deuterated solvent. Thin-layer chromatography (TLC) was performed on silica gel F254 plates (Merck, Darmstadt, Germany) with visualization by UV irradiation at 254 and 365 nm
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