5230-70-6Relevant articles and documents
Naphthoquinone based chemosensors for transition metal ions: Experiment and theory
Gosavi-Mirkute, Prajkta,Patil, Amit,Lande, Dipali N.,Chakravarty, Debamitra,Gejji, Shridhar P.,Satpute, Surekha,Salunke-Gawali, Sunita
, p. 55163 - 55174 (2017)
The synthesis and characterization of 2-((pyridine-2-yl)methylamino)naphthalene-1,4-dione (H-1), 2-((thiophen-2-yl)methylamino)naphthalene-1,4-dione (H-2) and 2-((pyridine/thiophen-2-yl)ethylamino) naphthalene-1,4-dione (H-3 and H-4) have been carried out. Molecular recognition abilities of these ligands toward transition metal ions in methanol, methanol-water, methanol-triethylamine or methanol-water-triethylamine mixtures, stoichiometries and association constants of H-1 and H-3 have been determined. It has been shown that H-1 and H-3 coordinate to metal ions via two nitrogen atoms and oxygen and exhibit remarkable selectivity towards Cu2+ ions in methanol or methanol-water mixtures, the complexation being accompanied by a color change from orange to intense blue. LOD (Limit of Detection) of Cu2+ with H-1, H-3 are 1.48 × 10-8 mol L-1 and 1.59 × 10-8 mol L-1 respectively. The vibrational spectra, 1H NMR chemical shifts and optical properties of H-1 to H-4 derived from density functional theory are also presented.
Design, synthesis, characterization and cation sensing behavior of amino-naphthoquinone receptor: Selective colorimetric sensing of Cu(II) ion in nearly aqueous solution with mimicking logic gate operation
Parthiban,Elango, Kuppanagounder P.
, p. 147 - 153 (2017)
An amino-naphthoquione receptor (R1) has been rationally designed, synthesized and characterized using 1H and 13C NMR, LCMS and single crystal X-ray diffraction studies. The receptor exhibits an instantaneous colour change from yellow to blue selectively with Cu(II) ions in water-DMF (98:2% v/v) medium. The results of UV–Vis and fluorescence spectral studies indicates that the mechanism of sensing involves formation of a 1:1 complex between R1 and Cu(II) ion. The proposed mechanism has been confirmed through product analysis using FT-IR, UV–Vis, EPR and HRMS studies in addition to magnetic moment and elemental analysis measurements. The formed [Cu(R1)Cl2] possess a square planar geometry. The binding constant for the interaction of Cu(II) ion with the present unsubstituted quinone is found to be relatively higher than that with quinones containing electron withdrawing chlorine atom and electron releasing methyl group reported in literature. The detection limit of Cu(II) ion in aqueous solution by R1 is observed to be 8.7?nM. The detection of Cu(II) ion by R1 in aqueous solution produces remarkable changes in the electronic and fluorescence spectra, which is applied to construct logic gate at molecular level.
Synthesis, antitumor activity and docking of 2,3-(substituted)-1,4-naphthoquinone derivatives containing nitrogen, oxygen and sulfur
Delarmelina, Maicon,Daltoé, Renata D.,Cerri, Murilo F.,Madeira, Klesia P.,Rangel, Leticia B. A.,Júnior, Valdemar Lacerda,Rom?o, Wanderson,Taranto, Alex G.,Greco, Sandro J.
, p. 1804 - 1816 (2015/09/22)
Eleven 2,3-(substituted)-1,4-naphthoquinone derivatives were synthesized in yields ranging from 52-89percent. These derivatives were evaluated for their cytotoxic effects on human lungs (H460), triple-negative breast (MDA-MB-231) and ovarian (A2780) cancer cell lines. Compounds 5f and 8 showed IC50 values of 3.048 × 10-5 mol L-1 and 4.24 × 10-6 mol L-1 for H460; 5c and 8 showed IC50 values of 2.16 × 10-5 mol L-1 and 1.60 × 10-5 mol L-1 for MDA-MB-231, and 5g and 8 showed IC50 values of 2.68 × 10-6 mol L-1 and 3.89 × 10-6 mol L-1 for A2780. Additionally, we conducted a docking study with the four most active compounds and the therapeutic targets PI3K and topoisomerase II showing the pharmacophoric conformation of these compounds.
