期刊
CHEMBIOCHEM
卷 23, 期 4, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.202100649
关键词
DNA binding; HAS binding; molecular docking; photophysical properties; quinoline
资金
- Coordination for Improvement of Higher Education Personnel (CAPES) [001]
- National Council for Scientific and Technological Development (CNPq) [305.379/2020-8, 409.150/2018-5, 304.711/2018-7]
- Research Support Foundation of the State of Rio Grande do Sul (FAPERGS) [17/2551-0001275-5]
This study reports the synthesis, structural analysis, and evaluation of the photophysical properties of twelve novel compounds, as well as DNA and HSA binding experiments and molecular docking studies. The compounds were synthesized using regioselective copper-catalyzed reactions and fully characterized through various spectroscopic and analytical techniques.
The synthesis, structural analysis, and evaluation of the photophysical properties of twelve novel 2-aryl(heteroaryl)-6-(4-alkyl(aryl)-1H-1,2,3-triazol-1-yl)-4-(trifluoromethyl)quinolines (6-8), where aryl(heteroaryl)=Ph, 4-Me-C6H4, 4-F-C6H4 and 2- furyl; 4-alkyl(aryl)=-CH2OH, -(CH2)(5)CH3 and Ph, are reported. Hybrid scaffolds 6-8 were synthesized at 77-95 % yields by regioselective copper-catalysed azide-alkyne cycloaddition (CuAAC) reaction of unpublished 6-azido-4-(trifluoromethyl)quinolines (2) with selected terminal alkynes (3-5). Azido intermediates 2 were obtained from the reaction of 6-amino-4-(trifluoromethyl)quinolines (1) and sodium azide at good yields (78-87 %). Compounds 6-8 were structurally fully characterized by H-1-, C-13- and F-19- and H-1-C-13 2D-NMR (HSQC, HMBC) spectroscopy, X-ray diffraction (SC-XRD) and HRMS analysis. Moreover, the photophysical properties, DNA- and HSA-binding experiments (bio-interactions), and molecular docking studies for compounds 6-8 were performed. These are discussed and compared with similar compounds from recent research.
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