Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles.
A set of novel quinolone-triazole conjugates (12-31) were synthesized in three steps in good yields starting from 2-phenylquinoline-4-carboxylic acid. All the intermediates, as well as the final 1,2,4-triazolyl quinolines were fully characterized by their detailed spectral analysis utilizing different techniques such as IR,1H NMR,13C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.
a University of Zagreb School of Medicine, Center for Translational and Clinical Research , Zagreb , Croatia.
Donatella
D
Verbanac
b Department of Chemistry , University of Delhi , Delhi , India.
Ritu
R
Malik
b Department of Chemistry , University of Delhi , Delhi , India.
Mahesh
M
Chand
b Department of Chemistry , University of Delhi , Delhi , India.
Khushbu
K
Kushwaha
b Department of Chemistry , University of Delhi , Delhi , India.
Monika
M
Vashist
a University of Zagreb School of Medicine, Center for Translational and Clinical Research , Zagreb , Croatia.
Mario
M
Matijašić
c Laboratory for Epigenomics , Division of Molecular Medicine, Ruđer Bošković Institute , Zagreb , Croatia , and.
Višnja
V
Stepanić
a University of Zagreb School of Medicine, Center for Translational and Clinical Research , Zagreb , Croatia.
Mihaela
M
Perić
a University of Zagreb School of Medicine, Center for Translational and Clinical Research , Zagreb , Croatia.
Hana Čipčić
HČ
Paljetak
d Department of Physiology and Pharmacology 'Vittorio Ersparmer' , Sapienza University of Rome , Rome , Italy.
Luciano
L
Saso
b Department of Chemistry , University of Delhi , Delhi , India.
Subhash C
SC
Jain
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011789:Quantum Theory; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry / Q000494:pharmacology*
C541577:2-phenylquinoline; D000900:Anti-Bacterial Agents; D000975:Antioxidants; D011804:Quinolines; D014230:Triazoles
1,2,4-triazole–quinoline conjugates; Cytotoxicity assays; DFT calculations using DPPH and CAA